Delicatessen

(1991)

If you like jet-black humor and surrealistic nightmares, you will find an embarrassment of riches in 1991’s French extravaganza, Delicatessen. Co-directors Marc Caro and Jean-Pierre Jeunet mix mood and setting like twisted Rembrandts, somehow crafting an unapologetically saccharine love story in the middle of a cannibalistic orgy.  It expertly draws upon our primordial fear that the butcher in the delicatessen (Jean Claude Dreyfus) might be using meats of a more “exotic” variety.  Credit Caro and Jeunet for choosing the menacingly impish Dominique Pinon as the perfect hero for their off-kilter story.  Part trickster, part innocent; Pinon supplies the conflicted humanity that’s foolish enough to look for love in the middle of Hell.

While comparisons to the work of Gilliam and Lynch abound, these are mostly atmospheric parallels.Delicatessen is a wholly unique experiment in absurdist comedy that more closely resembles a slapstick cartoon than a post-apocalyptic parable.  Suicidal tenants devise elaborate (and unsuccessful) contraptions to kill themselves, while underground Troglodytes plot their doomed rescue operations.  Things would certainly spin out of control were it not for the mesmerizing presence of Pinon, who anchors a cast of increasingly bizarre and undefinable characters.  It might be fair to charge Delicatessen with weirdness for weirdness’ sake, but it’s too deliciously wicked to care.

 – J.R. Kinnard

Billy Madison

(1995)

It doesn’t get weirder or funnier – or frankly, more quotable – for a 90’s kid than Billy Madison. This is Adam Sandler at his peak; before Jack and Jill, before The Ridiculous 6, before You Don’t Mess with the Zohan. It was an innocent time. A purer time.

The beautiful plot of Billy Madison is absurd: a wealthy man-child must return to school to inherit his fortune. This is literally every kid’s nightmare, right? Throw in the beautiful Bridgette Wilson-Sampras as the super inappropriate love interest, Norm Macdonald as the lovable BFF, Bradley Whitford as the villainous Eric Gordon (which I’ve never forgiven him for) and a fat wrestling teacher – it makes zero sense, but it’s strangely genius.

Honestly I think a string of quotes you know you repeated until they lost meaning will suffice to explain the impact of this silly comedy, like when you read about all those common phrases Shakespeare invented. “T-T-T-T-TODAY JUNIOR.” “If peeing your pants is cool, consider me Miles Davis.” “That’s quacktastic.” “Stop looking at me swan!” “Chlorophyll? More like bore-ophyll!” “Lady, you’re scaring us.” “O’DOYLE RULES!” “I award you no points, and may God have Mercy on your soul.”

 – Aubrey Nagle

Mrs. Doubtfire

(1993)

– Jon Gerblick

Wag the Dog

(1998)

In this age when American elections resemble a strange sort of real-life tragicomedy, Wag the Dog’s pointed satire of manipulative political machinery remains highly relevant to say the least. Barry Levinson directed this 1997 film from an Oscar-nominated screenplay by Hilary Henkin and David Mamet, which was itself based on Larry Beinhart’s novel. The picture co-stars Robert De Niro and Dustin Hoffman as a campaign advisor and the filmmaker he enlists to help produce a fictional war and divert attention from a president’s sex scandal. Of course, with that latter part of the scenario, Wag the Dog amusingly hit on elements of the Washington D.C. scene circa the late-‘90s in particular, but as funny and novel as the idea of a fabricated conflict was then, post-9/11, the concept is even more striking. And one can only imagine how the whole charade would unfold in the era of social media and our current penchant for first-before-accurate news reporting. In any case, the mutually-dependent tryptic of a complicit mass media, a consuming public, and savvy, often unscrupulous politicians is satirized in equal hilarious measure throughout the movie, especially as De Niro, Hoffman, and company ramp up fervent patriotism by whatever means necessary.

 – Jeremy Carr

That Thing You Do

(1996)

The lessons of That Thing You Do! are many: Life is long. Bands come and go. When a man in a really nice camper wants to put your song on the radio, you sign the papers. But the one that crescendoes above the film’s quotable asides is to go simple and go with your gut. The Erie, Penn., band that scales 1964’s pop charts only ascended because drummer Guy Patterson thought the titular hit sounded better fast during its first performance. And in retrospect, it’s hardly surprising Tom Hanks, who was making his debut as a writer/director in 1996, would espouse the virtue of trusting your instincts. That Thing You Do! marks the beginning of the Hanks brand, that of a simple, genuine-if-nothing charm and a keen, optimistic view of history.

If That Thing You Do! is a deeper cut on this list, it didn’t have bankability of comedy institutions on its side; it doesn’t really even star comedic performers. (Steve Zahn’s mock-airheadedness notwithstanding.) And despite the color palette of a malt shop, it was decidedly made for adults, probably why it didn’t hit at the box office and seems to inspire a biannual, online appreciation of its bountiful nuggets and nods: The harmony-laden jaunt that starts the movie is the previous epoch’s swan song. The bass player’s name is “the bass player.” Bryan Cranston ever-so-briefly plays a crewcut. One of Zahn’s best gags is referencing a movie band he was guesting in two scenes earlier. In large part, a film ages well by rewarding its fans for every return. Get out there and be a wonder, not an oneder.

 – Chance Solem-Pfeifer

The Sandlot

(1993)

There’s a time in everyone’s childhood when certain moments are so great that you wish growing up was impossible. The Sandlot epitomizes that desire by transporting viewers back to the San Fernando Valley in 1962 where a group of pre-teens spend their summer playing baseball at a local sandlot while also cracking an abundant supply of snarky one-liners. More than just a nostalgia-driven baseball movie, The Sandlot achieves its cult status mostly through the camaraderie of its young actors where you totally believe the collective friendship of the crew. This highly benefits the scene-stealing characters of Hamilton “Ham” Porter and Michael “Squints” Palledorous, both of whom have perfectly over-the-top deliveries of their greatest lines. Furthermore, the shenanigans the characters get into off the field are simple by design but firmly executed by director David Mickey Evans, especially the carnival chewing tobacco sequence. The Sandlot ultimately pulls off something remarkable that no other movie of the 90s could do and that’s be as equally great a baseball movie as it is a comedy. With that said its legacy shall last “For…ev…ER, For…ev…ER, For…ev…ER.”

 – Tyler Christian

Mystery Science Theater 3000: The Movie

(1996)

The most magical thing the Mystery Science Theater 3000 brand ever did was absolutely change the way we enjoy movies, while at the same time remaining a cult title that never quite achieved huge mainstream success.  (A two-hour comedy show about a man and two robots cracking wise over terrible movies doesn’t exactly have broad appeal.) Still, the brand had enough recognition that MST3K saw its one and only theatrical release from Universal Studios in 1996, appropriately titled Mystery Science Theater 3000: The Movie. One of those rare productions to suffer every imaginable behind-the-scenes complication outside of a newly dead cast member, that MST3K escaped relatively unscathed is either a miracle or a testament to the show’s creators and their ability to produce terrific work under some pretty tough stipulations. (The feature to be mocked had to hail from the Universal catalogue, be in color, and be “bad but not TOO bad.”) From there, the usual MST3K concept was watered down and manipulated by producer notes (less Dr. Forrester! shorter running time!) to the degree that it’s still painful for cast members to talk about the experience to this day.

But based on the final product, you would never know it.

While MST3K: The Movie enjoys a slight uptick in production design and cinematography, thanks to its film-scope budget, the spirit of the show remains firmly in place, and without having to cut for commercial breaks, it offers a smoother viewing experience. To be fair, one of Universal’s stipulations was for the best, as it led to the crew’s decision to send up This Island Earth—a film perfectly bad, but not too bad, paving the way for an experience less painful than, say, Santa Claus Conquers the Martians. While it never reaches the heights of majestic lunacy as the best episodes (Mitchell; I Accuse My Parents; Pod People), it still offers not just one of the best skewerings by the Satellite of Love, but the perfect gateway experience for someone who’d never before had the pleasure of watching a group of imprisoned men and robots tear up a crop of incredibly stupid low budgets movies that totally had it coming. Mike (host/writer Michael J. Nelson) and the bots (voiced by Kevin Murphy and Trace Beaulieu) let loose an array of sarcasm, absurdity, and amused observations that’s glorious to behold (“Should we be seeing this?” Tom Servo muses as an on-screen pilot wildly jerks the plane’s shifter between his legs) and will linger in your mind for as long as you hold admiration for MST3K’s eleven-year televised legacy…with perhaps more to come.

 – J. Tonzelli

Happy Gilmore

(1996)

Naturally, Adam Sandler’s magnum opus would end up on this list. The 1990s, when he and his buddies actually gave a shit. That could be the tagline for this movie: When Sandler Still Gave A Shit! Because, if you’ve seen this movie, it delivers on all of his comedic prowess. His shtick that he crafted over the years and through his time on Saturday Night Live is on full display in this 18-hole, gloriously violent, rage-fueled tournament of golf. The jokes are delightfully dumb, but there’s a sincerity in them that definitely diminished over the years.

Sandler really could play the down-on-his-luck-but-still-kinda-nice-but-he’ll-punch-you-too characters very, very well. Punch-Drunk Love is just the calmer version of Happy Gilmore. I grew up with this movie, too, so I suppose that added to my delight. My mom loves this movie. You love this movie. If you don’t love this movie, you love when Bob Barker kicks Sandler’s ass. Not even The Matrix‘s insane choreography can top “The Price is Wrong, Bitch.” Lets crack open a sick pack and watch this, guys? Sounds fun, right? Nobody ever says no to Happy Gilmore.

– Josh Heath

The Full Monty

(1997)

15 years before Magic Mike, 1997’s The Full Monty is the wry and heartfelt story of unemployed English steel workers who decide to put on a Chippendales-esque show in order to raise money for their various causes. Though the comedy is centered around the absurd/unlikely notion of the amateur exhibitionists and the various ‘fish out of water’ embarrassing situations they find themselves in as they prepare for the show, the film elevates itself on the razor-sharp dialogue and killer British wit.

Though largely upbeat, the dramatic plotlines which serve as motivation give the film wealth of emotion that turn what could be a silly film into one that swells to an optimistic and triumphant resolution. An excellent upbeat movie, ideal for a date-night watch, featuring great acting and a fantastic soundtrack. The Full Monty was a critical and box office success, received nominations for four Academy Awards (winning one), and in a 2000 poll was voted “the 49^th greatest comedy of all time” by Total Film magazine.

 – A.R. Magalli

Don't Be a Menace to South Central While Drinking Your Juice in the Hood

(1996)

If you existed in the 1990s the sub genre of films aptly titled “hood movies” came up in a big way from Boyz In The Hood to Menace II Society to Juice, et al.  The list goes on and on with plenty of solid deep cuts to explore. But leave it up to the Wayans Brothers (Keenan Ivory, Marlon and Shawn) to show that there is a lighter and incredibly absurd side to living in South Central, Los Angeles. Donning one of the best and most tongue twisting titles in comedy history Don’t Be a Menace to South Central While Drinking Your Juice In The Hood may not be the best film received critically, but it provided a vehicle that deflated the tension that had mounted in earlier in the decade.

That’s not to say one should go into the film expecting a social commentary that is going to resonate because the Wayans essentially made a 90 minute sketch routine that still kills two decades later. Classic bits (most are racially charged) such as a Korean woman trails Shawn and Marlon around a convenient store while a white guy in a suit robs the register would never make it into a film these days, in fact it’s a sketch we’d probably find on YouTube. While the brothers are now known for their movies being completely ignored Don’t Be A Menace held a special place where their obscenity-slinging comedy hit a fever pitch.

 – James Clay

Dogma

(1999)

It may not always sit well with certain factions of the audience, but there are few things more open to lampooning than organized religion. On the heels of his distinctly ‘90s trilogy of Clerks (1994), Mallrats (1995), and Chasing Amy (1997), writer/director Kevin Smith broadened his thematic and narrative scope and matured (somewhat) with Dogma (1999), arguably his funniest film. This star-studded story about a young abortion clinic worker who becomes humanity’s unlikely—and largely unwilling—heroine gets its comedic clout from a sharply written script and humorously inspired casting: Matt Damon and Ben Affleck as two fallen angels, George Carlin as a cardinal, and, because it’s the 1990s, Alanis Morissette as God. Given its subject matter and the fun it has with religious iconography and tradition (Buddy Christ, anyone?), Dogma unsurprisingly met with considerable controversy, particularly from the Catholic Church. As usual in these cases, however, once the furor died down, a very funny film with a surprisingly poignant commentary was left standing.

 – Jeremy Carr

Kicking and Screaming

(1995)

I first watched Noah Baumbach’s Kicking and Screaming a couple of months after I graduated from college. I’d majored in English with a concentration in Writing. I didn’t have a job. And I was terrified to dip my toes into the real world. The punchy witticisms and misadventures of Kicking and Screaming’s misanthropic post-grads came as a revelation to me. That screening lit the flame of a love-and-loathe relationship with the film’s aimless intellectuals that has lasted longer than most of my real life relationships. I’ve revisited this film a dozen times in the years since and I’m always amazed at how confident a debut it is. And how well the overarching themes hold up. Sure, the film’s mid-90s setting leaves it feeling a bit dated, but the timeless sentiment at the film’s core has only gotten more poignant with age.

We view much of that sentiment through the eyes of Grover (Josh Hamilton), a curmudgeonly wannabe writer who spends the entire film in free fall following a brutal graduation night breakup with Jane (Olivia D’Abo). Unable to move forward, Grover and his equally unmotivated buddies (Chris Eigemann, Carlos Jacott, Jason Wiles and a never funnier Eric Stolz) simply stand still – or even step backwards by returning to campus life. They smoke. They drink. They jump from one Freshman bed to the next. They screw each other over. And they do it all behind a screenplay that features Baumbach’s signature wit, insight and insanely quotable dialogue. I still find myself quipping lines from this movie at least twice a week. There’s just so many that still pop. It’s hard to believe that this was Baumbach’s first film. At 26, he was already one of cinema’s wittiest scribes. While he was clearly still developing as a visual storyteller, Baumbach’s Kicking and Screaming screenplay – and its tricky narrative structure – still ranks among his best work. And certainly among the best of the ’90s. Go Cougars!

 – Patrick Phillips

White Men Can't Jump

(1992)

White Men Can’t Jump offers one of the decade’s finest odd-couple pairings. Not since Murphy and Nolte joined forces in 48 Hrs. have a mismatched duo been so fun to watch. On one hand we have peak-era Wesley Snipes as fast-talking hustler, Sidney Deane. Deane is a role tailor made for Snipes’ movie-star charisma. On the other hand we have a young Woody Harrelson as Billy Hoyle. At the time, Harrelson was hungry to prove his stardom wasn’t bound to the world of sit-coms. The duo put on a masterclass in on-screen chemistry, which helps make their love-hate bromance one for the ages.

Not being a straight up comedy only works in the film’s favour. Two straight hours of cracking wise can easily devolve into buffoonery. White Men Can’t Jumps’ crushing emotional beats bring the viewer down so low that when the jokes return, the gut-busting highs feel that much higher. The film’s “dramedic” ebb and flow creates an exhilarating emotional roller coaster, leaving viewers with a comedy high that lingers long after the final credits role.

 – Victor Stiff

Metropolitan

(1990)

Whit Stillman’s debut film, first in a loose cultural trilogy including Barcelona (1994) and The Last Days of Disco (1998), is a relentless barrage of droll philosophizing, cultural commentary, and cutting wit. Centered on the faux-ritualistic debutante ball scene of Manhattan society in the late 80’s, the film works like a comedy of manners for its era, delighting in the contradiction of a self-aggrandizing community that revels equally in the putting on of complex airs as in the intentional disregard of their own presumed customs.

Packed with eye-rollingly dry sips like “I prefer good literary criticism. That way you get both the novelists’ ideas as well as the critics’ thinking” and pithy pseudo-philosophic pretentious gulps like “the cha-cha is no more ridiculous than life itself,” it’s no surprise that the work was called ‘Modernly Austen-esque’ or that Stillman later went on to adapt the famed authoress’s work for the screen in this year’s Love & Friendship.

Unquestionably one of the best dialogued films of the modern era, Metropolitan is a notable poster-child for the success an elite script can achieve even when filmed on a shoe-string budget.

 – A.R. Magalli

Dirty Work

(1998)

Dirty Work has a 17% rating on Rotten Tomatoes, probably making it the lowest critically rated film on this list. However, there is something wonderful about this movie. On paper the plot is stupid and bloated with pointlessness, but in execution, its two lead men seem so uninterested in anything that’s going on, making it a bizarrely perfect anecdote to the sea of lesser comedies produced during this decade.

Dirty Work is directed by Bob Saget, written by Norm Macdonald and stars himself and Artie Lange. The basic plot involves them starting a company that professionally destroys people’s lives. In one particular scene, Norm begins finding dead hookers in the trunks of every car on the set of a used car dealer’s live commercial shoot. That may not sound incredibly funny, but I can tell you this: hearing Norm Macdonald deliver the line, “I’ve never seen so many dead hookers in all my life!” was a staple moment in my comedic upbringing. 

 – David Costill

L.A. Story

(1991)

Anyone could have written a comedy about Los Angeles, so well-known are its stereotypes. But it took someone like Steve Martin, who truly understands and loves the city, to create the gently snarky valentine that is L.A. Story. As weather man Harris Telemacher, Martin navigates a crazy-quilt of comic tropes, all infused with a true affection: he nonchalantly trades gunfire with other freeway drivers while debating brunch options with his girlfriend; he points out side-by-side Tudor and “four-door” mansions in a poke at the city’s mismatched architecture; characters must submit credit histories before dining at a trendy new eatery whose waiters rap the menu; upon telling young love interest, Sandee (spelled “Big S, small a, small n, big D, small e, big E…and there’s a star at the end”), that her breasts feel weird, she responds, “Oh. That’s because they’re real.” These moments are given shape by a charming, almost naïve love story that’s infused with magic realism. As Harris falls for visiting Englishwoman Sara (Victoria Tennant, later married to Martin for a time), he gets love advice from a sentient freeway sign. Their kiss awakens stone lions in a private garden. He “wishes” a rainstorm at the airport that prevents her return to England. The two aspects fit perfectly together in a unique, hilarious, sharply observed film that Harris might call “wonderful, wonderful, wonderful, wonderful, wonderful, and most wonderful and yet again, wonderful.”

 – M. Robert Grunwald

Half Baked

(1998)

Before Dave Chappelle became a legend for his show on Comedy Central, he was known for a little stoner comedy called Half Baked. The film, written by Neal Brennan and Chappelle, doesn’t have much plot to speak of, but that’s really missing the point. The joy of films like these is that they mimic hanging out with your best friends: shooting the breeze and seeing who can crack up each other first. Drug-related comedies can be a slog after the high has worn off, but the energetic personalities of Chappelle, Guillermo Diaz, and Jim Breuer make the bizarre feel truly authentic. Otherwise, how would anyone sit through a movie with a dog that flies out of a high-rise window after a few puffs, a love interest named Mary Jane, and a jail sentence set off by giving a police horse more junk food than it could handle? Like the Marx Brothers comedies of yore, Half Baked serves as a reminder just how funny slap-dash situations filled with ridiculous people can be. And, best yet, it’s not necessary to be high when watching Half Baked for the film to still be funny.

 – Colin Biggs

Galaxy Quest

(1999)

When it comes to parody, there’s basically two kinds: the mean-spirited parody, which seeks to ridicule the source material (like all those terrible genre parodies from the 2000’s), and the affectionate parody, which takes its subject apart so thoroughly and with such care that it’s clear the creators made it out of love. Galaxy Quest, sometimes even considered a “missing” Star Trek movie, is definitely the latter. Following a crew of washed-up actors from an 80’s sci-fi phenomenon, their lives of hitting the convention circuit with people they barely liked 20 years ago are anything but exciting. As it turns out, however, their fandom extends beyond the planet Earth, and the peace-loving Thermians have gone to great lengths to perfectly recreate the ship from the TV show–now all they need is that crew of space heroes to pilot it.

With Tim Allen starring as the arrogant, Shatner-esque Jason Nesmith, who loves nothing more than the adoration of his fans, and the late Alan Rickman as the classically trained Alexander Dane, who’s less than thrilled with the direction his career took, it might sound initially like there’s some spite present after all. A lot of the humor in the film certainly comes from the situation that the characters are in from the start, and the kind of obsessive fandom that sprouts up around sci-fi shows like Star Trek, however these things are also key to the resolution of the plot, and understanding and accepting who they are is what’s most important. Galaxy Quest is as much a celebration of what it means to be a fan, and the special relationship that stars and fans have, while never forgetting that it’s first and foremost a comedy. Whether you’re into sci-fi or not, Galaxy Quest is a 90’s comedy not to be missed.

 – Carlyle Edmundson

The Truman Show

(1998)

What if the universe really does revolve around my actions and reactions? Andrew Niccol’s Academy Award-nominated screenplay for The Truman Show revolves around that very existential quandary, all while satirizing public devotion to television and celebrity culture. Like Jim Carrey’s performance as the eponymous Truman, the film is appropriately livewire when it needs to be, giving Carrey enough room to spread his comedic wings inside a decently dystopian premise. But, the script intelligently recognizes when to pause the laughs and confront some thought-provoking questions, such as why we so require the most minute of details to relate to these characters we place even above ourselves. And though it may not seem like much, what’s most remarkable about Peter Weir’s film is inability to submit to despair. Even where there is still uncertainty by the film’s conclusion, hope still looms on the horizon.

 – William Penix

Grosse Pointe Blank

(1997)

As the nineties came to an end and a new millennium dawned, it became hard for an entire generation not to spend an entire era looking back on what came before. In Grosse Pointe Blank, professional hitman Martin Blank (John Cusack) is depressed, disenfranchised with his job and seemingly beyond help- reluctantly, he accepts the invitation to go to his ten year high school reunion. The fact he bailed on prom night to join the army is the reason he has spent the intervening years in this state, after all.

The movie may represent the pinnacle of nineties cool, but it is a film with a heart firmly in the eighties; everything from the all killer-no filler soundtrack to the stunt casting of Dan Aykroyd as a professional assassin helps reimagine the cornerstones of the previous decade’s pop culture for a more jaded generation. It is a film that could only ever exist in a post-Tarantino cinema landscape- undeniably of its time, even as it spends the entire duration romanticizing times gone by. Both funny and genuinely heartfelt, it is no surprise it remains an enduring cult classic.

 – Alistair Ryder

Bottle Rocket

(1996)

Some directors take time to find their signature style. For Wes Anderson, everything fell in place in his debut; all his signature trademarks, from garish production design to offbeat comic sensibility, have remained intact and unchanged in the decades that have followed Bottle Rocket. It almost wasn’t to be. Bottle Rocket was a monumental flop upon release, to such a degree that Owen Wilson (who, along with his brother Luke, made their film debut here) even considered joining the Marines after it failed to find an audience.

Thankfully, that was never to be- and this bonkers deconstruction of the heist movie template has had its influence felt everywhere in contemporary cinema in the years that followed. The Ocean’s trilogy and Ant-Man both strained to replicate the goofy humor in the screenplay for their heist tales, whilst Wes Anderson quickly begun the transition into one of American cinema’s most recognizable, not to mention influential, directors.

 – Alistair Ryder

Liar Liar

(1997)

If there was a sweet spot in Jim Carrey’s career between “living cartoon character” (The Mask, Ace Ventura) and dramedy darling (The Truman Show, Eternal Sunshine of the Spotless Mind), then it must be Liar Liar. This is one of the best examples of a wonderful premise that prompts the action and then gets out of the way. Carrey plays Fletcher Reede, a selfish, amoral lawyer who works too much and never makes time for this son. When he breaks a promise to attend the kid’s birthday, a blow-out-the-candle wish renders Reede physically incapable of telling a lie for the next twenty-four hours.

Despite its high concept, Liar Liar is an unpretentious, no-nonsense movie that knows what it’s here to do: unleash Jim Carrey hilariously spewing unfiltered Id over everyone he comes across. From the “pen is blue” scene to the show-stopping boardroom roast, there are a half a dozen unforgettable comic set pieces that allow Carrey to have a ton of fun with a great script. The formula worked so well that Carrey later tried to recapture the magic in Yes Man, to diminished returns. Liar Liar does succumb to one classic comedy blunder, which is the need to tie up the story resulting in a third act with fewer laughs; nevertheless, I think it’s Carrey’s funniest film. Stay for the gag-reel during the credits.

 – Daniel Stidham

The Player

(1992)

To call Robert Altman’s The Player a comedy might initially come across as rather reductive. And the film is indeed much more than any one thing, skipping between genres and tones. But all of its commentary on the Hollywood studio system is couched within a winking satire of the intersection of art and commerce (on a scale of two other great Hollywood portraits, it’s somewhere between the nihilistic apocalypse of Barton Fink and the self-aware love letter of Hail Caesar!). Tim Robbins stars as a struggling producer who winds involved in a plot more layered than any actual writer could dream up (besides Player screenwriter Michael Tolkin). The film is deeply funny, from the opening tracking shot featuring criticism of modern whiplash editing to Lyle Lovett’s Lynchian turn as a quirky detective. The Player wears a multitude of personalities, and dons all of them sublimely: it’s a noir-infused satirical comedic thrilling character study… with heart.

 – Josh Oakley

South Park: Bigger, Longer & Uncut

(1999)

This feature-length film version of Comedy Central’s animated comedy powerhouse continues with the South Park brand of
vulgarity, but, with the addition of a 90 minute running time, adds a
world-ending incident to the hay. Now, the foul-mouthed foursome must
save the world. Audiences were familiar with the 30-minute episodes,
but the feature-length movie gave Trey Parker and Matt Stone a chance
to chip in on the war over violence, obscenity, and censorship.

No one wants to be preached to, of course, so the message is spread
with 14 brilliant songs, including the (miraculously) Oscar-nominated
“Blame Canada.” Only Parker/Stone could write comedic songs that are
simultaneously hilarious but connect on the same emotional level as
the material they’re satirizing. A peek of what was to come with “The
Book of Mormon” later. Most importantly, South Park: Bigger, Longer,
and Uncut marked the transition from shock for its own sake to a
larger critique of society, and the show we know today.

 – Colin Biggs

A League of Their Own

(1992)

More than just a misfit baseball comedy a la Major League, but not as heavy as Bang the Drum Slowly, A League of Their Own solidified its position as the perfect “dramedy” before that term ever existed. And director Penny Marshall, who hasn’t directed nearly as many films as she should have, knows a thing or two about meshing comedy and drama, being that her two previous films were the undervalued Awakenings and the utter classic Big. Call A League of Their Own what you want—a comedy with dramatic elements, a drama with moments of comedy, or a dramedy that perfectly marries the two—but when it wants to be funny, it’s very funny, and when it wants to pull at the heartstrings, it does so easily and without cheap manipulation. (Seriously, if you’re not crying every single time Betty Spaghetti gets that telegram, you have no soul.)

A League of Their Own revisits the very real All-American Girls Professional Baseball League, an unexpected byproduct of many men enlisting to fight abroad in World War II, leaving baseball fields barren across the country. Planted into the middle of this alien environment are the close but conflicted Keller sisters, Dottie (Geena Davis) and Kit (Lori Petty), who join the league after being solicited by baseball scout Ernie Capadino (Jon Lovitz). Relying on a mishmash of previous baseball film tropes—the tried and true transition from underdogs to superstars, with a little Bad News Bears thrown in for good measure—A League of Their Own also acknowledges multiple real-world conflicts to remind the audience that just because these women are playing a game, it doesn’t mean it’s always fun. For them, this new baseball league isn’t just an opportunity to do something new, but a chance to escape the constraints of being just a “woman” confined to less than desirable professions or statuses. Madonna’s Mae Mordabito is a former burlesque dancer desperate for a way out. Megan Cavanaugh’s tomboyish Marla Hooch, raised like a boy by her well-meaning father, finally finds an environment where she feels normal, and people she can call her friends. The crowd mocks them as they take the field; radio columnists defame their not-so-womanly women’s league; they are managed by an alcoholic curmudgeon (Tom Hanks) more interested in scratching his balls than forming a line-up. Bt most importantly, their husbands are at war, and at any moment, that telegram from the war department can arrive with their name on it, alerting them that someone they love isn’t ever coming home.

Everything heavy aside, A League of Their Own permanently bequeathed to the masses one of the most quotable lines of all time: “There’s no crying in baseball!”

 – J. Tonzelli

What About Bob?

(1991)

There are two types of people in this world: those who love What About Bob? and those who haven’t yet seen it. A fantastic showcase of Bill Murray’s primal comedic splendor, both subtle and overt – he plays Bob Wiley, a hypochondriac+ with separation anxiety who puts the ‘cute’ in acute and is wily to boot. He’s a brand new patient of narcissistic Dr. Leo Marvin (Richard Dreyfuss with the tightest of beards), a Freud-obsessed psychotherapist.

This physical comedy tics off all the boxes to ace the test of time, despite the movie being more than old enough to vote. From Murray’s disaffected toothbrushing to mantra chanting, Heimlich Maneuvering and Tourette’s syndrome breaks, it’s a lighthearted portrayal of heavier subject matter at its best. The re-watching highlights for me were the subtleties and darker edges that may have been missed upon initial evaluation, like the Marvin’s goth, nihilist child candidly spouting bleak fatalisms.

The slight subversiveness of the time seemed to be testing the waters for dark comedies of the future (Frank Oz also directed late eighties Dirty Rotten Scoundrels and 2007’s Death at a Funeral), and we’re all in a happier, funnier place for it – because comedy, like fashion, repeats itself. You could say it was farce-sighted? or not.

 – Susie Nuessle

Home Alone

(1990)

You can’t have Christmas or a 90’s comedy list without Home Alone. I’ll admit that this is in no small part due to nostalgia. It’s nearly as prominent as A Christmas Story when it comes to holiday movie traditions. That said, there’s a reason for its popularity. Chris Columbus directs John Hughes’ script about a young boy (Macaulay Culkin) who is left behind when his family goes out of town for Christmas and must defend his home against a pair of dim but persistent thieves (Joe Pesci and Daniel Stern). The most memorable part of the movie is pure slapstick. Young Kevin rigs the house with booby traps, any of which would kill a normal person; but these Daffy Duck types keep coming back for more. It’s a more violent Three Stooges act that’s great for a few kicks, but it wouldn’t work if the rest of the movie wasn’t also funny and sweet.

Culkin was the definition of precocious – neither an angel nor an irredeemable brat. Much of the humor is mined from his attempts to improvise an adult life for himself. Home Alone is a particular brand of comfort food that always feels appropriate right about the time the first flakes start falling.

 – Daniel Stidham

Clerks

(1994)

If members of the Generation X crowd could choose a movie that best reflects their era, Kevin Smith’s Clerks would certainly be a top pick. A pinnacle in both 90s comedies and independent filmmaking, Smith’s execution of the film’s day-in-a-life structure is superb as he chronicles the comic misadventures of convenience store clerks, Dante and Randall. The chemistry between Brian O’Hallaran and Jeff Anderson flows so naturally, and their banter on everything from Death Star politics in Star Wars to vents on the occasional customers they encounter are sidesplittingly hilarious. Also as someone who worked in retail for nearly eight months, activities like those became things I’d do on a daily basis. Clerks is as great as dialogue-driven movies can get and the blunt, unapologetic tone Smith carries for how graphic some conversations get never ceases to make my insides hurt from laughter.

 – Tyler Christian

Ace Ventura: Pet Detective

(1994)

The 90s were truly Jim Carrey’s decade, scoring huge hits with Ace Ventura: Pet Detective, The Mask, and Dumb & Dumber. I was 8 or 9 years old at the time and I can remember catchphrases from all three of those films were literally inescapable. Even if you’d somehow managed to not lay an eyeball on Ace Ventura: Pet Detective you knew “Like a glove,” “Re­he­he­he­heaaally,” and so forth. It was a no­-brainer that Carrey would go on to become the king of mainstream comedy for at least the rest of that decade and into the 2000s.

What’s more remarkable is how well the film stands up today. With so-­called comedies arriving in your local cinema constantly containing less than half a dozen laughs in the entire picture (if they’re lucky), it’s astounding just how laugh out loud funny Ace Ventura continues to be. The thing is just jam packed with jokes and it’s Carrey’s impeccable comic timing that allows them to consistently land with such gut busting force. Go back and take another look at Ace Ventura even if you’ve seen it a million times but especially if it’s been awhile. If you’re not laughing hysterically within five minutes… just wait longer.

 – James Casey

My Cousin Vinny

(1992)

I can distinctly remember seeing My Cousin Vinny in theaters in 1992, and being massively entertained, even if some of it was a little over my head at the time. Many years later, I re-watched the film, expecting that the nostalgic respect I had for it would wear off and I’d suddenly notice all the flaws my nine-year-old mind hadn’t picked up on, only to have the exact opposite happen: not only did the film still hold-up, it was a lot better than I’d ever realized. Dale Launer’s screenplay is remarkably clever, and tight, fully committing to the murder mystery that sets the entire film into motion. While a lesser comedy would simply use its set-up as an excuse to get to eventual joke delivery, My Cousin Vinny takes its plot seriously, and still manages to be hilarious.

Much of the film’s success rests in its cast. Joe Pesci won his Oscar for Goodfellas while this film was being made, and while it’s easy to see his role as Vincent LaGuardia “Vinny” Gambini as just another wise guy stereotype the actor would find himself stuck with for his whole career, Vinny is far removed from Pesci’s Goodfellas character Tommy DeVito. Pesci’s Vinny is likable; the type of fuck-up you root for, and he’s matched perfectly with Marisa Tomei as his girlfriend, Mona Lisa Vito. Tomei won the Academy Award for Best Supporting Actress, and rightfully so: her performance is electric here. She’s fast, funny and has great chemistry with Pesci (despite their considerable age difference). The script also takes care to show that despite her airhead Jersey Princess nature, Mona Lisa is quick-witted and incredibly smart, to the point where she becomes a big part of helping Vinny with his case. Pesci and Tomei are supported by Fred Gwynne, giving a fantastic performance as the disbelieving judge assigned to the case. After an eternity being known as Herman Munster (and “that old guy from Pet Semetary”), Gwynne’s performance here demonstrated how much range and acting prowess he had (unfortunately this would be his last film — he died of cancer in 1993). If you haven’t seen My Cousin Vinny since catching an edited-for-TV re-run on TNT years ago, and can only remember the “Two yutes” joke, seek the film out again: you may be surprised at how great it is.

 – Chris Evangelista

The Cable Guy

(1996)

Some guy on this website already wrote about how The Cable Guy was way too ahead of it’s time. I’ll try not to retread too much of what I’ve said previously, because hearing an echo of my voice is obnoxious enough to drive even the deafest man insane.

The Cable Guy is a modern, mature comedy that handles a dark concept – stalking- with a real sense of place, purpose, and direction. It’s not dour, though, don’t worry. It’s a fine-tuned joke machine powered a slew of rad cameos, and by a subtly creepy yet energetic-as-ever performance by Carrey. His character is a blend of wounded puppy, Jim Carrey, and that guy creeping outside your barred-off window at night. You feel bad for him, even as his behavior becomes more erratic. It’s all about this layered character, and they actually put effort into this, man. I quote it almost every day. That lisp is almost iconic. Once you see The Cable Guy, you won’t soon forget it. And remember, it came out in 1996. If you squint, you could almost assume it came out just a few years ago.

 – Josh Heath

There's Something About Mary

(1998)

There’s Something About Mary is a rare bird of a comedy that settled itself somewhere in between insanely raunchy— see quote, “Is that hair gel?”— to thoughtful and endearing. Bobby and Peter Farrelly (The Farrelly Brothers) were on a hot streak (Dumb & Dumber, Kingpin) back in the 90s that heralded many classic scenes (and quotes) that set the comedy world on fire.

There’s Something About Mary is their magnum opus, if one such term exists for a movie where a guy zips his genitals up into his pants. This is low-brow comedy, make no mistake, but teetering the line of rom-com, to gross out comedy took some major skill and gave Ben Stiller, Cameron Diaz, Matt Dillion and the long lost Lee Evans some of the best moments of their career. Finding a way to ground the bricolage of disgusting sight gags was and is a stroke of genius. Of course the cast went on to other hits in their career, but the Farrelly Brothers just haven’t found the right chemistry to shock and amuse audiences since.

– James Clay

Friday

(1995)

If you’ve ever wanted to see the author of AmeriKKKa’s Most Wanted and future star of Are We There Yet? watch another man have a bowel movement (twice, actually), F. Gary Gray’s 1995 slacker comedy Friday is the movie for you. Although Ice Cube had done the movie thing before, Friday (which he penned the screenplay for) marked the true beginning of his Hollywood career, the moment he deemphasized music in favor of acting. Chris Tucker and Ice Cube are like a modern Laurel and Hardy: one big, the other small; one always high, the other straight; one goofy and accident-prone, the other a little more responsible. I don’t blame Cube for focusing most of his energy on acting; he’s a much better physical comic than he usually gets credit for, and Friday allowed him to flex his muscles (and those iconic eyebrows) in ways that weren’t just with his mouth. Recommended if you like: getting high, taking the day off, and watching rappers watch other people poop.

 – Nathan Smith

The Bird Cage

(1996)

An adaptation of the French play La Cage aux Folles, Mike Nichols’s The Birdcage remains a timely socio-cultural farce even twenty years after its release. With much of the focus being on Robin Williams’ Armand Goldman and Nathan Lane as his partner Albert, we bear witness to their carrying the proceedings through Williams’ usual playful energy and Lane’s unabashed theatricality. The laughs are relentless, largely due to Williams and Lane’s performances, but also because of the latter half’s antics so frenetically directed by Nichols. Public opinion of homosexuality has changed significantly since 1996, but much progress is left to be made, and where The Birdcage, as well as its source material, remains most poignant is its painting of a utopian environment where homosexuality is accepted, but still must deal with stereotypes both outside and within those confines.

 – William Penix

Dumb & Dumber

(1994)

It’s important for a comedy to have just as many small laughs as big ones. By the time you finally get around to watching a movie in full, chances are you’ve already seen quite a few of the big laughs in the trailer which kind of diminishes the comedic value during the feature length viewing experience. The small laughs & random/unexpected comedic moments are the glue that binds everything together.

This is certainly the case with Dumb & Dumber and every Farrelly Brothers movie from the 90’s, which is what made them so successful. Dumb & Dumber was Jim Carrey in his prime. He was just coming off of the success of Ace Ventura, and his stint on “In Living Color” was still fresh in our minds. And while Jeff Daniels may have been more of a well rounded actor at the time, trying to trade laughs with Jim Carrey is still pretty intimidating and Daniels carried the movie just as much as his partner. Both stars hold their own in Dumb & Dumber.

A lot of wacky physical comedy & distorted goofy faces were to be expected, but in my personal experience, the older I get the more I find myself (and others around me) bringing up the little random moments in Dumb & Dumber over all the “big” laughs (the Big Gulp scene outside the convenient store, the way Jim Carrey tilts the bottom of the cup as Jeff Daniels drinks the ex-lax coffee, lines like, “That’s a Lamborghini. You might wanna hold on to that”). Maybe it’s maturity or just an appreciation for subtlety. And the best thing about small/minor comedic moments is that they’re sometimes easy to miss, especially when sandwiched between scenes of Jim Carrey being Jim Carrey, so you have a reason to go back and watch the movie again to catch what you may have missed.

 – Marcus Pinn

Clueless

(1995)

Amy Heckerling’s 1995 teen comedy Clueless often gets dismissed as yes, just another teen movie, but in the past few years, it’s assembled a dedicated following among cinephiles. Most of this could be chocked up to how fun it is, but I also think it can be attributed it to something else. More than almost any other movie I’ve ever seen, Clueless is not just the most exemplary entry in its genre but an impeccable satire of that genre, embodying perfectly and skewering ruthlessly the formula by which it plays. Heckerling’s ever-so-loose adaptation of Jane Eusten’s Emma is one of the best, if not the best, teen films ever made, a slice of screwball fantasy awash in valley speak, high school slang, and lush surfaces But it’s also a lot deeper than many of its detractors and even its fans give it credit for, a filmic utopia that uses the tropes and trappings of teen comedy to explore the dynamics of high school friendships. As Cher Horowtiz might say, Clueless has more meaning than a Pauly Shore movie, with razor wit, iconic catchphrases, and gorgeous outfits to boot.

 – Nathan Smith

Austin Powers: International Man of Mystery

(1997)

The combination of the two sequels’ abysmal, sub-sophomoric quality and their inexplicable saturation of the mainstream popular consciousness in the early 2000’s has left the first Austin Powers movie with a lot of bad baggage to account for. If the mere mention of the franchise dredges up painful memories of everyone’s terrible Fat Bastard impersonations, I implore you to view the first movie on its own merit – because it’s great!

International Man of Mystery sports genuine wit and satire to back up Mike Myers’ constant mugging. The greater your familiarity with the first few James Bond movies, the more references you’ll recognize as being plucked wholesale from them, but that knowledge isn’t even really necessary to appreciate what they’re lampooning. Every trope, every incongruity, every bit of non-logic from spy movies past is reckoned with in Austin Powers, and it’s delightful. Is there sophomoric humor? Yeah. Is there corniness? Sure. Is there mugging? God, yes. But there’s also smart, insightful comedy, and that’s something the sequels sorely lacked.

– Jon Gerblick

Tommy Boy

(1995)

Watching Chris Farley sway back and forth while singing “Fat guy in a little coat…” may be peak comedy in the 90s. But how could it not be? At this point, Farley was making it big on “Saturday Night Live,” as was his co-star David Spade, and this may be one of the better culminations of that partnership. The endearing quality of Tommy Boy really comes from Farley’s lovable goofball routine, which he built a lot of his career on while on “SNL,” and the fact that we can easily forgive a lot of his misgivings – even while Spade’s Richard is unable to.

Tommy Boy‘s comedic set pieces are strong with my favorite moment coming when a deer, which is presumed to be dead, erupts with life and begins to tear down the pristine car that Richard holds so dearly. A lot of the story beats in Tommy Boy are schmaltzy and worn out, but the endearment of Farley’s charm and the fact that he sells being a screw-up son who is just looking to prove himself works in their favor. It shares a lot of the same qualities of some of the more delinquent comedies that are coming out today (Farley feels like a definite precursor to what we’ve seen from Adam Sandler in this movie), but there is an undercurrent of heart that seems to lack in a lot of Sandler’s work. Farley succeeds where Sandler doesn’t because we feel more justified in rooting for him than the vindictive and rude personalities that the latter “SNL” star plays. Plus there is no way this movie could’ve failed when it came out… how do you lose with Rob Lowe? Sure, he was being an ass, but it is the 90s! That is peak Rob Lowe!

 – Zach Dennis

Ed Wood

(1994)

When’s the last time Tim Burton made a great movie? Some may argue 2003’s Big Fish, but that film — while occasionally lovely — has more than a few problems. No, the last time Burton bucked his lazy cliches and produced a great work of art was 1994’s biopic Ed Wood. Written by Scott Alexander & Larry Karaszewski, Ed Wood gives the once-dubbed “Worst Director of All Time” a weird, loving tribute. Played by Johnny Depp (in one of his last great performances, before he embraced endless schtick), Ed Wood shows the director as a man determined to make his dreams of being an Orson Welles-like filmmaker a reality, and refusing to let a little thing like his massive lack of talent get in the way. Martin Landau turned in an award-winning performance as Bela Lugosi, whom Ed befriends late in the former Dracula actor’s life. The warm friendship that develops between Ed and Bela is the heart that drives the film, but Ed Wood is essentially a story about believing in yourself, even if you have absolutely no reason to do so. Ed Wood’s films are terrible — but they’re terrible in that special, eye-opening way that only a loving creator could design. Ed loves his non-sensical stories about grave robbing aliens and incoherent mad scientists, and there’s something magical about that. Filmed in glorious black and white, Ed Wood is the closest Burton may ever come to creating a masterpiece.

 – Chris Evangelista

Quick Change

(1990)

The New York of today can be overwhelming, but it’s nothing compared to the New York of 20+ years ago. NYC then was dangerous. As a piece in Salon put it, “In the 1970s, ’80s and early ’90s, New York was viewed as one of the world’s most dangerous metropolises — a cesspool of violence and danger… Friends who lived here during that time talk of being terrified to use the subway, of being mugged outside their apartments, and an overwhelming tide of junkies. Thirty-one one of every 100,000 New Yorkers were murdered each year, and 3,668 were victims of larceny.”

Howard Franklin and Bill Murray’s 1990 film Quick Change was released at the cusp of big change in the city (as the 90s went on, the Big Apple would turn into a much safer place to inhabit). The genius of Quick Change lies in how it takes the potentially deadly chaos that the city had yet to crawl out of it and turn it into something hilarious. The film opens with a lengthy bank robbery-turned-hostage-standoff. Bill Murray plays the bank robber, who arrives on the scene in a full clown get-up. Eventually it’s revealed that two of Murray’s “hostages” — played by Geena Davis and Randy “Star Whackers” Quaid — were in on the job with him. And while the three criminals get away from the robbery unscathed, getting out of the city will prove to be much more difficult. Quick Change is often hilarious, but there’s a melancholy that layers the film that likely didn’t sit well with audiences expecting a riotous Bill Murray comedy (the film eventually made its budget back, but was considered an overall box office disappointment). Quick Change eventually earned the cult status it deserved, and remains one of the best comedies of 90s.

 – Chris Evangelista

Kingpin

(1996)

The Farrelly Brothers’ grimy bowling-based comedy Kingpin holds a special place in my heart for two reasons. The first reason being that it’s endlessly re-watchable. The jokes are layered enough that even after you tire of the film’s gross-out gags, there are so many great one-liners spewing from the mouth of everyone on screen that you’ll find something new to laugh at every time the film comes on TBS.

The second reason Kingpin is so memorable is because it’s the first comedy that I was able to laugh along with my father, a man whose love for Animal House and Porky’s eludes me to this day. Kingpin is able to bridge generational gaps in comedy appreciation, a feat most comedies fail to achieve, no matter how much more brilliant they may be compared to the slapstick stylings of the Farrelly Brothers’ low-brow masterpiece.

Also, you don’t get much more 90s than Kingpin’s soundtrack which is heavy on Freedy Johnston and Blues Traveler.

 – Jeff Rollins

Being John Malkovich

(1999)

The auspicious cinematic debut of both writer Charlie Kaufman and director Spike Jonze, Being John Malkovich is a singular film about Craig (John Cusack), a neurotic, selfish puppeteer who can’t find a job in “today’s wintry climate”, his dissatisfied wife Lottie (Cameron Diaz), and his co-worker Maxine (Catherine Keener), who discover a portal that that slips them into the head of John Malkovich for 15 minutes before they are promptly defenestrated on the side of the New Jersey Turnpike.

Bizarre, self aware, and wholly obsessed with itself yet unconcerned about its status as original, it’s a film that should be nothing more than a gimmick, yet manages to be one of those rare comedies whose images, style, and ideas are no less important than the writing or acting. From the claustrophobic tight shots of Craig’s miserable office job on the 7 ½ floor, to the manic energy of handheld frames barely giving Craig or Lottie breathing room, to the sheer abstract absurdity when Malkovich takes the plunge into his own mind, where he must scream but can utter no word but his own name, it’s a film that always knows what it’s saying and how to say it, even if the audience doesn’t know how to react.

Where many films manage to pass for psychological depth while doing no more than a phrenological survey, Being John Malkovich goes spelunking through the psyche, eagerly plumbing the subconscious to riff on existential philosophy, sexual appetites, celebrity worship, and the fear of meaninglessness. It remains a radical film not only through its Meta narrative and mind-on-its-sleeve sensibilities, but through its explorations of identity and sexual repression.

Election

(1999)

There’s a Tracy Flick in every high school: the insufferable overachiever whose hand is always first in the air and who volunteers for every extracurricular activity in sight. Like most of them, their smug confidence irks both students and faculty. But in Tracy’s case, an ostensibly consensual affair that ruined a teacher has made teachers doubly uncomfortable around her. But civics teacher Jim McAllister (Matthew Broderick) has had enough of Tracy’s goody-goody act to want to take her down a peg. He sees his opportunity in Tracy’s campaign for student council president, which is curiously fervent considering she’s running unopposed. Her comparison with the Coca-Cola company is not lost on Jim. The war that Jim ends up waging against Tracy, while his personal life crumbles spectacularly, makes for brilliant dark comedy.

Election was the second collaboration of director Alexander Payne and his co-writer Jim Taylor, whoseCitizen Ruth was an underrated mini-masterpiece, and who would go on to make About Schmidt, Sideways, and The Descendants. Here, they take delicious glee in Jim’s growing inability to cope with the fallout of his war on Tracy and his affair with the wife of his disgraced colleague. The filmmakers pitch-black humor offers something else: there’s a certain perverse pleasure in seeing the unflappable Ferris Bueller, his face swollen from a bee sting, become the victim of his own weaknesses.

 – M. Robert Grunwald

Dazed and Confused

(1993)

Richard Linklater movies are often funny in the way your best group of friends were in high school… only more so. Personalities bounce back and forth, and laughs are elicited less from set-pieces than the authentic rhythms of characters who either know each other well or not at all. Circumstance takes a backseat to those relationships in Linklater’s first masterpiece, Dazed and Confused. There are certainly efforts to draw out pure humor, namely from the presence of Matthew McConaughey in his breakout role (“high school girls…” is more widely quoted but I’ve always been partial to his delivery of “it’d be a lot cooler if you did”). But a lot of the comedy in Dazed derives from an understanding between the audience and the film, those moments that pop up as they do in real life. Linklater’s filmography is full of this aching authenticity materialized as charm and wit. With Dazed and Confused he told us something about the pains and pleasures of growing up, but only after the keg ran out and the last joint made its way around the circle.

 – Josh Oakley

Wayne's World

(1992)

Mike Myers was the 90s version of early-day Bill Murray. His self-aware smart-ass persona was perfectly balanced out with an earnestness that existed in all his characters, from Austin Powers to his iconic roster of SNL mainstays (Dieter, Linda Richman, Simon, etc.), but his turn as Wayne Campbell, co-host of the Aurora, IL cable access TV show “Wayne’s World” will forever be Myers’ biggest and most influential contribution to comedy.

So popular was “Wayne’s World” as a piece of sketch comedy that SNL head-honcho Lorne Michaels decided to give it a go as a feature length movie. And while most SNL sketches cannot (and historically have not) succeeded when stretched to 90 plus minutes, Wayne’s World is something special. Rather than just turn in an extended comedy skit, Myers and company used Wayne’s World  as means to skewer anything and everything they saw fit. From selling out to dude culture to the very genre of comedy itself, no topic is safe from the wise-cracking and whipsmart script.

Aside from being infinitely quotable, Wayne’s World also delights in iconic sight/sound gags such as the “Bohemian Rhapsody” car ride, Garth Algar (Dana Carvey) dancing to Jimi Hendrix’s “Foxy Lady” as he imagines himself seducing a woman at the local donut joint, and and incredible grand finale that involves several different versions of how the movie might end. Sha-wing.

 – Jeff Rollins

Office Space

(1999)

Office Space has the distinct honor of being one of the more recent movies in existence to find its (cult) audience through video store rentals & word of mouth suggestions instead of its initial (unsuccessful) theatrical run (films like Gummo and Donnie Darko also share the same honor).

So much has been said about Office Space over the years so in an effort to try and not repeat too much of what’s already been said, I’ll just reiterate the fact that it was a movie that managed to convey what so many sad and depressed people hate about office cubicle life but didn’t have the ability express it properly. All jokes aside, working in an office cubicle can be depressing (and I have most of you reading this trumped because not only do I work in an office cubicle myself, but I also draw & design office cubicles for a living).

From the overall subject matter to all the Michael Bolton jokes and now-famous expressions like, “a case of the Mondays,” – Office Space is a timeless classic that appeals to a large demographic of human beings.

 – Marcus Pinn

Rushmore

(1998)

It’s a testament to Wes Anderson’s singular vision that Rushmore could slot into a ‘saddest movies of the ‘90s’ list as easily as it does our ‘best comedies’ compilation. Though it never fully succumbs to its maudlin underbelly, Anderson’s tale of angsty outsiders, true love lost and first love unrequited carries a potent sense of loss and regret throughout. Much of Rushmore’s sallow tone spawns from Bill Murray’s indelible portrayal of midlife crisis bound Herman Blume. It’s easy to forget, but the mid-90s saw Murray at a bit of a career crossroads and ready to shed class clown persona he’d cultivated over decades prior. Rushmore would become the defining moment of the funnyman’s career, heralding the arrival of Bill Murray – Actor. The wily veteran’s dry, emotionally bare performance found a peculiar counterpoint in the wide-eyed, bushy-browed face of Jason Schwartzman. It’s Schwartzman’s endearing portrayal of teenaged playwright Max Fischer at the center of Anderson’s film. In his first big-screen role, Schwartzman brings a vital naiveté to Fischer’s youthful hubris that keeps the precocious teen from becoming a mean-spirited brat … even when he’s being a mean-spirited brat.

It’s the absurdity of Max’s and Herman’s relationship – and subsequent rivalry over Olivia Williams’ tender-hearted teacher, Miss Cross – that drives much of the comedy throughout Rushmore’s quippy – “O, R they?” – screenplay. As an unexpected love triangle blooms, Anderson and Co-Writer Owen Wilson find inspired, not-quite slapsticky ways to raise the emotional stakes to hilarious extremes. Almost lost in the mix is a delicate, heartbreaking performance from Williams that makes all the madness seem worthwhile. When Rushmore premiered in 1998, Anderson became an instant indie superstar. Considering that Anderson took the tepid commercial reception of his debut film Bottle Rocket (1996) as inspiration for Rushmore’s lovable band of rejects, that must have been particularly satisfying. After all, it was Bottle Rocket’s key crew members – DP Robert Yeoman, Composer Mark Mothersbaugh, Editor David Moritz and Production Designer David Wasco – that helped make Rushmore a breakout success. Since the film’s release, Anderson & Co. have gone on to make some of the wittiest, heartfelt films of the past 20 years. But Rushmore is where all the whimsical, idiosyncratic, Brit rock-infused, super slow-mo symmetry became the Wes Anderson gospel – particularly in the film’s pitch-perfect final moments. Just to be clear, everything you love about Wes Anderson’s films was spawned from the last five minutes of Rushmore. That this film continues to inspire generations to go out into the world and ‘find their Rushmore’ is a tribute to its interminable charms. Sic Transit Gloria, my friends. Of course in Rushmore‘s case, the glory may never fade.

 – Patrick Phillips

Groundhog Day

(1993)

Bill Murray may be one of the most beloved figures ever, and while that could be construed as strong hyperbole, try and think of a way to just violently dislike the guy. While it is easy to reference a lot of his other work, such as Stripes or Caddyshack or even his early bits on “Saturday Night Live,” as the more defining moments of Murray’s career, Groundhog Day may be his magnum opus due to the ultimate pairing of Murray with director Harold Ramis. It is easy to dictate the movie just be the schtick that it is pulling off – a man has to repeat the same day over and over again after becoming stuck in a time loop while covering Groundhog Day in his hometown – but the distant, relatability of Murray’s Phil works perfectly. He has played this character before, even playing it alongside Ramis in Ghostbusters, but it seems here like Murray is channeling the culmination of all those roles. He is always an arrogant ass, but we love him regardless and in Groundhog Day, it is easy to be transfixed with his conundrum.

Returning home and having to engage with a place you never wanted to be again is a challenge that a lot of us face (and don’t we wish we could be as funny as Murray when we do it). But what works best about the film is its ability to play with its constrained world (or the idea of being stuck in time) and allow for humor to be created from that. In what could be a monotonous concept, Murray sells the small moments (punching Ned Ryerson in the face, finally) and he is an expert of playing this unlikable character in such a likable way. I’m not sure of any other comedic actor who could thread that line so carefully, and it really is an indication at his ability to tackle more dramatic roles later in his career in Lost in Translation, Broken Flowers, or The Life Aquatic with Steve Zissou. While his character in Groundhog Day may not go as dark as some of those souls, it is Murray playing the Murray that we were introduced to him with, but a variation that seems to be in transition from the past and into the present. Time is moving for the actor even while the movie is stuck in a loop.

 – Zach Dennis

The Big Lebowski

(1998)

Some movies redefine your character, transform your personality and plant themselves among the most cherished items in your pop culture lexicon. To say The Big Lebowski is one of those movies for me is putting it mildly. Joel and Ethan Coen’s Fargo follow-up is not only another masterpiece from two of the greatest filmmakers of all-time, but quite possibly the most endearing, bewitching and instantaneously quotable comedy ever, not merely from the ’90s. It’s a perfect balancing act of quirky characters, warmly-realized backdrops and razor-sharp writing that never loses its step, and it’s one of the rare satires that only continues to get funnier, funnier and funnier upon revisiting. It also only feels sweeter and more poignant over time. Once you begin to let the dude roam your heart, you’ll never want him to leave. Let him abide.

Jeff Bridges and John Goodman give their greatest performances to date as Jeffrey “The Dude” Lebowski and Walter Sobchak, a mismatch pair of wayward souls who connect solely through their mutual love of bowling. One is an unemployed stoner with an undisclosed past, with undisclosed sources of wealth (an early draft of the script notes his father was the creator of the Rubik’s Cube). The other is a Vietnam veteran with a poor temper and an ex wife he remains inexplicably close with, going out of his way to take care of her temperamental dog at any moment’s notice. When two strangers break into The Dude’s house and piss on his hospitality and rug, he’s furious and Walter isn’t happy either. The two then end up on a windy road around town, connected to a series of random events they never should have gotten themselves into in the first place. Of course, a few dead bodies are left to waste in the process. Nothing out of the ordinary for a Coen film, but what makes The Big Lebowski such a classic is its reverence for the bizarre. The wacky characters are the forefront, and they ride everything into the ground in their own individual fashion, but despite their oddball personalities, they never feel too strange or too out-of-the-ordinary.

They’re grounded in a lovable, eccentric fashion, and there’s a clear chemistry shared between these two through their war-torn path. Their objectives are almost simple to a fault, but that’s what makes it better. It’s the filmmakers proving that they can make a mountain of an ant hill, and right off the heels of their biggest success to date. It’s a film that dares to be outlandish and provoked, but let’s that informs the story and its characters rather than lets it define the movie on the whole. This is the distinction that helps make it such a great piece of work. And, of course, all the wonderful one-liners — which I could go on and on quoting, but should be enjoyed in their natural habitat. The Big Lebowski is a film about misunderstanding and poorly-defined goals, but it’s one of the sharpest, clearest and most pointed movies ever made. It’s a tour-de-force and the cream of the crop of the stoner comedy genre, and the best film to center around a urine-soaked rug ever. Plus, Sam Elliott plays a cowboy and narrates the whole film. Literally, what else can I do to sell you on this movie? Shut the fuck up and watch it already!

 – Will Ashton