The 25 Best Comedy Movies of the Last 25 Years, #10-1
Our list of the 25 Best Comedy Movies of the Last 25 Years continues with #s 10-1. If you missed our first 15 picks, you can check out Part 1 right here.
10. The Big Lebowski (1998)
Directed by Joel Coen
Stoner comedies of errors are most effective if you just sit back and let them wash over you. The Big Lebowski features Jeff Bridges in his defining role as The Dude: a White Russian-drinking, pot-smoking, aimless middle-aged guy who reacts to life with a perpetual shrug. He’s the kind of dude who, to paraphrase Liz Lemon, is transitioning his pajamas to daywear — which makes his forced involvement with criminals all the more comical. The Dude just wants to live his life, man, with his own personal brand of Zen. Getting involved in a kidnapping and some shady encounters is the sort of annoying, active living in which he’d prefer not to engage. The Coens approach the classic hardboiled detective story through a haze of pot smoke, putting their signature abstract spin on this slice of life. Equal parts bizarre, absurd, and fantastic, The Big Lebowski is enhanced by performances from Steve Buscemi’s nebbish Donny, John Goodman’s temperamental Walter, and Julianne Moore’s eccentric Maude — all of whom create unforgettable characters caught up in The Dude’s foggy orbit. Each of them are so oddly specific, and it’s that specificity that lends itself so well to comedy. — Britt Hayes
9. 21 Jump Street (2012)
Directed by Phil Lord and Christopher Miller
It’s become a common joke that the careers of directors Chris Miller and Phil Lord feel like a series of increasingly improbable dares. No one has proven themselves more capable of spinning crap into pure gold quite like these two. With 21 Jump Street, they took what should have been a lame update of a dated ’80s cop series and made a comedic masterpiece, a thoroughly self-aware joke machine that cranks out one-liners, sight gags, slapstick, and scathing satire at a pace that beguiles the mind. Miller and Lord’s background in animation serves them well; they fill every frame with as many jokes as humanly possible, ensuring that not a single moment goes by without a potential laugh. If you have only seen 21 Jump Street (and its equally funny sequel) once, you haven’t seen it at all. Few comedies have rewarded viewers who actively scour every scene looking for hidden gags. This movie is filthy and frenetic, sweet and weird, assured and chaotic. It has no right to work. But it does. And it makes everyone else look lazy. — Jacob Hall
8. Wet Hot American Summer (2001)
Directed by David Wain
Wet Hot American Summer might as well be written wholly from infinitely quotable catchphrases. The entire thing is brilliant and bizarre, a send-up of camp films that manages to layer in every possible cliché and trope with glorious abandon. Wet Hot revels in being purposely nonsensical (time is totally elastic, the world is almost destroyed, something about a goat), though every frame and every scene feels artfully laid out. It’s madness. Wet Hot American Summer is best described as a gleefully “stupid” comedy, one that somehow manages to find time to pay homage to Easy Rider, be pro-gay marriage, and make jokes about Jesus being old. It’s a smorgasbord of insanity and it only gets funnier with age. If NASA wants to broadcast a film into space for aliens to watch, this is the one. It’s kind of perfect. — Kate Erbland
7. Wayne’s World (1992)
Directed by Penelope Spheeris
In 1992, I went to see Wayne’s World in the theater, and laughed harder than I ever had in my entire life. The whole movie cracked me up, but the scene that absolutely blew my 11-year-old mind was the one where public-access cult heroes turned network sellouts Wayne (Mike Myers) and Garth (Dana Carvey) are on the set of their new big-budget show. Their sleazy boss (sleazy Rob Lowe) insists they need to dedicate a segment of the show to a thinly-veiled commercial. Wayne refuses. “Contract or not,” he vows, hoisting a slice of Pizza Hut pizza into the air, “I will not bow to any sponsor!” “Maybe I’m wrong on this one,” he adds as he samples a Dorito, “but for me the beast doesn’t include selling out!” The sketch goes on like that, and then culminates when Lowe gives Wayne a choice, and Wayne raises a Pepsi into the air and announces “Yes, and it’s the choice of a new generation!” (That was the Pepsi slogan at the time. Ask your parents.) That part had me cackling so hard I legitimately fell out of my chair, something that’s never happened to me before or since. Wayne’s World still holds up to this day as a hilariously meta satire and a charming buddy comedy. Just make sure you put on some kneepads before you hit play on Netflix, or you could hurt yourself. — Matt Singer
6. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)
Directed by Larry Charles
Before Sacha Baron Cohen’s Borat became a frat house favorite with bro-friendly catchphrases like “It’s niiiice!” he was a cable TV host so obscure Cohen could travel the country in character and no one had any idea who he was. And that’s the basic conceit of Borat, the uproarious mockumentary from Cohen and Seinfeld writer Larry Charles: Borat explores the United States and offends everyone he meets along the way. The film, whose full title is actually Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan, was kept quiet by Fox, who didn’t even confirm its existence until a teaser trailer was released. But, once it started to screen for audiences, the hype instantly grew. When he first saw the film, Larry David supposedly laughed so hard he had to stand up and ask them to pause the movie (if he’s anything like us, it was during the extended and wildly explicit nude wrestling scene). Equally shocking and hilarious, Borat may now best be remembered for “Wawaweewa!”, but you’ll always remember your reaction the first time you saw it. — Mike Sampson
5. MacGruber (2010)
Directed by Jorma Taccone
Although the recurring Saturday Night Live sketch MacGruber is based on was a one-note parody of TV’s gadget-building secret agent MacGyver, the film version has bigger fish to skewer. Director Jorma Taccone and star Will Forte set their sights on every single ’80s action hero and take a dump (albeit, a loving dump) all over them. Forte’s MacGruber is a mulleted narcissist with a terrible fashion sense and a profound ability to sink to new lows ... but he’s also a skilled special forces commando who has a history of getting results despite his jaw-dropping incompetence. It’s an inspired comic creation, the super-spy re-imagined as an entitled brat who lives every moment to justify his very narrow worldview.
As funny and fearless as Forte is (and this is a role that asks him to humiliate himself every two minutes or so), MacGruber works because Taccone surrounds his leading man with a brilliant cast. Kristen Wiig and Ryan Phillippe make for inspired foils and the great Powers Booth lends his military mentor genuine authority, which makes the lunacy around him all the funnier. Taccone even lets Val Kilmer run wild as the villainous Dieter Von Cunth, a baddie with a name that you can’t say out loud in public and a series of hilariously justified reasons for hating MacGruber’s guts. All of these people together would make for a great comedy, but Taccone ensured the film’s immortality by shooting and editing MacGruber with the technical precision of a true action spectacular. Long live MacGruber. (KFBR392.) — JH
4. Step Brothers (2008)
Directed by Adam McKay
Regardless of what the rest of this list might tell you, Adam McKay’s sibling rivalry comedy Step Brothers ranks as his greatest achievement. It’s the ultimate man-child comedy, transforming its stars into bumbling, unreasonable brats trapped in adult bodies — a perfect reaction to the slew of contemporary comedies featuring regressive but empathetic dudes loved for their irresponsibility and laziness. Will Ferrell and John C. Reilly are total naturals as obnoxious bros forced together by the marriage of their beleaguered middle-aged parents. Ferrell showcases the sort of outlandish, boorish performance we’ve seen variations on before, but Reilly and his innate talent for juvenile affectations are the real highlight. He delivers lines like a typical pre-teen boy, as if he has marbles in his mouth or may be slightly intoxicated.
Together, the pair not only destroy their parents’ homes and lives, but absolutely shatter your funny bone with their effortless chemistry. But Ferrell and Reilly are just two components of this insanely great and often-underrated comedy: Kathryn Hahn turns in an utterly wacky performance as the desperate and sexually-repressed wife of Adam Scott, a snide egomaniac who has a strange desire to turn his clan into the next Partridge Family and who delivers one of the film’s best lines. — BH
3. Bridesmaids (2011)
Directed by Paul Feig
There’s an old cliché about comedies that have gooey emotional cores being “hilarious and heartfelt,” but it’s a cliché because it’s true. Infusing very funny films with genuine pathos and emotion isn’t an easy thing to do, but it’s so often worth it, simply because the results are that much richer. Bridesmaids is one of those “hilarious and heartfelt” movies that transcends the tired cliché by going outsized – it is extremely funny (and not afraid to get dirty or gross or raunchy in the service of that humor), but it also tells a highly emotional story. (Have I cried while watching Bridesmaids? Yes, I have.) The basic plot – weddings are wacky and friendships are tough – is bolstered by deeply felt performances that walk the tightrope between deliriously goofy (Rebel Wilson) and unexpectedly dramatic (Rose Byrne).
Bridesmaids is perfectly encapsulated by its “throw the giant cookie on the ground, lash out at a chocolate fountain” scene (that old chestnut!), as Kristen Wiig flails about, getting filthy and embarrassing without an ounce of restraint, as a horrified Maya Rudolph looks on, disbelieving that her best friendship has turned into, well, whatever the hell this is. It’s so funny and it’s so sad and it’s so relatable, giant cookie and all. — KE
2. Anchorman: The Legend of Ron Burgundy (2004)
Directed by Adam McKay
What can be said about Anchorman that hasn’t already been said? And I mean literally; I’ve had entire conversations made up of Anchorman lines. It has seeped into the cultural consciousness like no film since Caddyshack. Judging a movie based on its innate quotability is a mixed bag; sometimes overwhelming popularity can hurt a movie. (See: Napoleon Dynamite.) But Anchorman is so damn funny and so damn rewatchable, it’s hard for any one gag to get completely worn out.
It’s a bit silly to claim a movie “changed the face” of anything, but it’s hard to imagine a comedy as influential as Anchorman over the past 25 years. It propelled the careers of Will Ferrell, Steve Carell, and Paul Rudd into a new era of superstardom. Its absurd brand of lunacy defies any real sense of story structure or logic (to wit: a whole other separate movie featuring Amy Poehler and Maya Rudolph was born from the outtakes); things just happen because they’re funny. A bunch of insanely talented people came together at the right time with the right project and made some magic happen. Anchorman is a perfect storm of comedy; it’s a sketch stretched to feature length, which doesn’t sound like it should work, and if they tried it again under any different circumstances, it may not have. But in this case, it did. We love lamp. — MiS
1. Groundhog Day (1993)
Directed by Harold Ramis
Groundhog Day is the best comedy film of the last 25 years, but it’s more than that: It is also a guide to living. It takes place over the course of a single day, but that one day contains something like the totality of existence; all of its joys and agonies, all of its hopes and frustrations, all of its virtues and vices. If there is such a thing as a perfect comedy, this is it. The closing credits play over a shot of a clear blue sky. This, it seems, is a little piece of heaven itself.
Its chief resident is Phil Connors; the actor who plays him is Bill Murray. As the movie begins, Phil is the pompous, miserable weatherman for a local affiliate in Pittsburgh. Against his wishes, he’s sent to nearby Punxsutawney, Pennsylvania to file a report on Groundhog Day. There, he becomes trapped, first literally by a blizzard he inaccurately predicted would miss the region, and then metaphysically when he begins to repeat February 2 over and over again, hundreds or possibly thousands of times.
The screenplay by Danny Rubin and director Harold Ramis brilliantly and hilariously plumbs the depths of Phil’s despair before nudging him onto the path of enlightenment. And everyone involved does a marvelous job of nailing all the little details of continuity to ensure that it really does feel like Murray is living the same day over and over (the script supervisor, Judi Townsend, deserves a Presidential Medal of Freedom for her work keeping all those variations of the same day straight).
Groundhog Day is the story of a man who thinks he's a god, who becomes a god and finally learns how to be a man. In the early scenes, Phil looms over the earth (or at least the national weather map on a green screen) blowing frontal systems around; later, when snow blocks his route back to Pittsburgh and a cop blames the weather, his delusional response is “I make the weather!” Then he’s given actual divine power — he becomes immortal and, at least within the confines of sleepy Punxsutawney, all-knowing — and after a great deal of trial and error (and cruelty, and excess, and groundhog robbery) discovers goodness within himself. The message of Groundhog Day is simple but powerful: Our time on this earth is limited, but if we live like it’s unlimited and think about others instead of ourselves, great things — and great movies — can happen. — MaS