25. Zoolander (2001)
Image Source: BBC
Zoolander the movie is an awful lot like its titular male model: Stupid to a fault, but also endearing and charming despite itself. Ben Stiller, who both directs and stars, understands the exact amount of effort needed to exert a story about models brainwashed as assassins for a shadowy cabal of clothing manufacturers. From A to Z, this spoof of a film. It picks apart our cultural fixation with fashion, thinness, celebrity, money, lust, sex, and power. It also benefits from a worthy villain in Will Ferrell’s high-strung Mugatu. His manic exasperation is fueled by being so aware of the absurdity of the world he inhabits. Zoolander could have been a forgettable comedy. Instead, it became a pop-culture staple.
24. Shaun of the Dead (2004)
Image Source: Mental Floss
This fantastic action comedy introduced a winning combo. It featured sparring buddies Nick Frost and Simon Pegg, and the master of style in director Edgar Wright. Pegg plays a sad sack who turns out to more brave slaying the walking dead than he ever thought he would. Shaun of the Dead is so funny, it takes a moment to realize how weirdly emotional it can be. By mashing up a witty romance with a zombie apocalypse, hilarity is bound to ensue.
23. Superbad (2007)
Image Source: Mental Floss
Taking a page out of the Judd Apatow book, co-writers/BFF’s Seth Rogen and Evan Goldberg went back to their drafted teen comedy with dick drawings, dirty jokes, and a little heart and soul. This hilarious movie about teenagers being teenagers was a runaway success. And it wasn’t just McLovin that made it so. Michael Cera and Jonah Hill’s friendship was as genuinely sweet as it was startlingly accurate to the way teens spoke and behaved. All this, plus a near-perfect turn from Emma Stone. Super, indeed.
22. 40 Year Old Virgin (2005)
Image Source: Bustle
Judd Apatow’s first film still remains as his best. This sweet but vulgar formula has been imitated numerous times in a decades-plus since its release. The 40 Year Old Virgin is a surprisingly insightful. It has great heart, as well as a lovable hero in Steve Carell. Andy (Carell) is indeed 40 and a virgin. He resorts to surrounding himself with video games and action figures. The script is filled with small but perfect one-liners. Carell’s charming naivety — paired with the improvisational crudeness of Paul Rudd, Seth Rogen, and Catherine Keener — make this a perfect comedic balance.
21. The Grand Budapest Hotel (2014)
Image Source: Byrd Theater
From the opening frames of The Grand Budapest Hotel, you know you are in Wes Anderson Land. It’s gorgeous and lush, and vibrantly colorful. The twisty narrative with multiple time frames (set during two World Wars) is infectiously entertaining and hilarious. This is in large part especially to Anderson faves Bill Murray, Owen Wilson, Tilda Swinton, Edward Norton, Adrien Brody, Jason Schwartzman, and Harvey Keitel. Led by the remarkable Ralph Fiennes, this lovely Anderson film has filled every nook and cranny with mustache-twirling comedians.
20. School of Rock (2003)
Image Source: Express
There were always hints of Jack Black’s potential greatness (i.e. Tenacious D). However, it took director Richard Linklater to get a full service performance out of him. No one has been able to harness Black’s manic energy quite like him. Funny, charming, and catchy as hell, this movie has inspired actual schools of rock to open up across the country and teach impressionable kids the power of a good riff. The comedian’s passion for the guitar gods of rock made him the only choice to play a would-be rocker who fakes his way into a fifth grade substitute teaching gig (whilst ultimately developing his musically gifted students into his band). Take my word for it, play this comedy loud.
19. Bridesmaids (2011)
Image Source: NPR
Decades from now, it will be clear that this story — about a thirty-something stuck in a rut along with her fellow bridesmaids — was a magic bean sprouting the future of studio comedies. SNL vets Maya Rudolph and Kristin Wiig pair with fresh faces like Rebel Wilson, Ellie Kemper, Chris O’ Dowd, and Melissa McCarthy to form a proudly feminine film. Along the way, it’s become one of the most successfully comedies of all-time. Not everyone can do physical comedy, but Wiig’s behavior on the flight to Vegas would win the respect of Lucille Ball.
18. Anchorman (2004)
Image Source: Mental Floss
Two years after his triumphant run at SNL, Will Ferrell cemented his transition to movie stardom with this master of a comedy. Ferrell and his frequent collaborator/co-writer/director Adam McKay found the perfect role for the comedian as the sexist, alpha-male privileged, buffoonish San Diego newscaster Ron Burgundy. When the news director goes crazy over stories about cute animals at the zoo, the film is right on target. And its quotable as hell — from Burgundy’s declaration that San Diego is German for a whale’s vagina to his cry that he’s “in a glass case of emotion.”
17. Tropic Thunder (2008)
Image Source: ew.com
Tropic Thunder was an absolute phenomenon upon its initial release 10 years ago. It was the movie that finally pushed The Dark Knight off the top of the box office. Thanks to Robert Downey Jr., it became the rare comedy hit to receive Oscar attention (earning him a Best Supporting Actor Nomination). For director-star Ben Stiller, this film was magnum opus territory. He assembled an all-star cast to play his costars in this movie within a movie (Jack Black, Jay Baruchel, Brandon T. Jackson, Danny McBride). With Downey’s ridiculously extreme method acting, and Tom Cruise (nearly unrecognizable) as a crass, studio executive, it is still considered one of the best comedies to come out of the 21st century (and rightly so, “dammit!”)
16. Mean Girls (2004)
Think of high school hierarchical hell. A world full of J.V., desperate wannabe girls who eat their feelings. Oh, and don’t forget The Plastics — led by the Queen Bee, Regina George. The film became an instant teen classic, and boasts one of the most quotable scripts of the past 20 years. Pitched somewhere between Heathers and Clueless, it may contain all the usual cliches of a teen movie (party scenes, awkward adolescent romances, and pressures of fitting in). However, Fey’s script renders it far edgier and funnier than any of its peers. And because of this, Lindsay Lohan — or should I say Cady Heron — will forever live in our hearts.
15. The Royal Tenenbaums (2001)
Image Source: OKC MOA
Just about everything is a little off-kilter in this quirky story about a wildly dysfunctional family. Set in New York City, Wes Anderson’s sprawling third film mines laughter and pathos from one family’s pent up resentment, unexpressed desires, and overall disappointment. Gene Hackman plays the neglectful patriarch of a family that includes his ex-wife (Anjelica Huston) and his three children Chas (Stiller), Richie (Luke Wilson), and the adopted Margot (Gwyneth Paltrow). All of the kids achieved tremendous success in their younger years. Royal (Hackman) and Etheline (Huston) split up, which then causes the family fell apart. The children grow to be neurotic failures. With The Royal Tenenbaums, Anderson revealed himself to be a highly original comic talent.
14. Knocked Up (2007)
Image Source: SkyNews
This is Judd Apatow’s chronicle of a one-night stand gone horribly, horribly wrong. In lesser hands, Knocked Up could have devolved into a cliched odd-couple farce. However, Apatow’s attention to detail that made this is cult classic. Idiot-boy Ben Stone (Seth Rogen) knocks up gorgeous Alison Scott (Katherine Heigl) on a drunken first date. This forges a truce with his lifelong enemy: Maturity. Talk about a buzz kill. Still, this is a film of unexpected gravity. For all of the rom-com’s relentless gags, it has a heartfelt story arc that keeps you rooting for Rogen’s underdog until the very last scene.
13. Legally Blonde (2001)
Image Source: Chicago Tribune
Before we were quoting mean girl Regina George, we were quoting Elle Woods. Having just been dumped by her Harvard-bound boyfriend for being too much of a Marilyn Monroe and not enough Jackie Kennedy, sorority president Elle Woods (Reese Witherspoon) proceeds to prove to him that she can be both. Suddenly, this clever blonde is acing her LSAT’s and recording a video essay in a sparkly pink bikini. Surprise! She gets accepted into Harvard Law School. This is the film in which Witherspoon bent-and-snapped her way into our hearts, and ends up defying expectations while staying true to herself.
12. Wet Hot American Summer (2001)
Image Source: Mental Floss
The camp spoof that finally gave talking vegetable cans the onscreen time they deserve. The film made less than $300,000 at the box office in 2001, with mixed reviews from critics ranging from “hilarious” to “ cinematic torture.” Yet, Wet Hot American Summer has become so firmly established as a cult classic that it has yielded not just one Netflix series prequel — 2015’s Wet Hot American Summer: First Day of Camp — but a second Netflix sequel: Wet Hot American Summer: Ten Years Later. We can also thank this hilarious comedy for introducing us to soon-to-be superstars including Bradley Cooper, Amy Poehler, Elizabeth Banks, and Paul Rudd.
11. I Heart Huckabees (2004)
Image Source: Toledo Blade
I Heart Huckabees is a punctuation in the career of director David O Russell. Mark Wahlberg is a philosophically woke fireman. Jude Law is a sleazy department store executive with an identity crisis. Naomi Watts is his girlfriend — the bikini-weaning Huckabees spokesmodel. Jason Schwartzman is the sensitive environmentalist getting his life audited by detective Lily Tomlin and Dustin Hoffman. Isabelle Hubert is… well… the devil? It doesn’t really matter because what all these characters represent is essentially the director himself. A light comedy about meaning and existence, the film fuses lowbrow physical comedy and deep thoughts to create a movie that’s eager to risk looking ridiculous.
10. The Trip (2010)
Image Source: Electic Pop
If you don’t know who Steve Coogan or Rob Brydon is, well, that’s part of the point. In The Trip, Coogan and Brydon play mid-forties comedians who never really made it. Essentially, they play slightly fictionalized version of themselves. The first in a series of travelogues that buds/collaborators Coogan and Brydon did for the BBC that eventually turned into a feature length road movie. The Trip consists of the two driving through the English countryside, sampling food and wine, and turning dueling Michael Caine impersonations into a hilarious game. This is a great deal more entertaining than it sounds — largely because the two actors are gifted mimics. Brydon is the better one, although Coogan may disagree.
9. Juno (2007)
Image Source: Betty
Jason Reitman’s film Juno is just about the best film that came out of 2007. It’s insanely smart, very funny, and very touching. When 16-year-old Juno MacGuff (Ellen Page) discovers she’s pregnant after a sexual encounter with her long time friend Pauly (Michael Cera), she finds herself forced to make a choice: Should she get an abortion, or should she go to term and give the baby up for adoption? As well as this, she must come to terms with her true feelings for Paulie — who is still very much in love with her. The film features a witty and warm script from Diablo Cody (which she won an Oscar for). Committed performances from the whole cast make Juno and immensely lovable comedy.
8. O Brother, Where Art Thou? (2000)
Image Source: IMDb
The film that helped launch a thousand bluegrass revivalists, the Coens’ O Brother loosely riffs on The Odyssey for this goofy Depression-era adventure of three escaped convicts seeking treasure. Tim Blake Nelson plays Delmar, John Turturro plays the irascible Pete, and George Clooney plays the loquacious Ulysses Everett McGill. They all deliver laughs, no matter how over the top their performances may be. Clooney is hammy and wide-eyed in one of the best roles of his career. The Coens are serious about their hero’s salvation and sincere in their affection for the time period. The warmth of O Brother, Where Art Thou continues to be a disarming and hilarious surprise.
7. Step Brothers (2008)
Image Source: Indiewire
The best moments of Adam McKay’s films with Will Ferrell are in the downtime moments when Ferrell is allowed to ruff on something so mundane, you can’t help but laugh until you cry. In this regard, he has no better scene partner than John C. Reilly, who perfectly matches him in every way possible. There’s no better showcase for their flights of nonsense than this 2008 film about two 40-going-on-20 year olds forced to live together after their parents get married. Only to becomes allies in a war against adulthood, Ferrell and Reilly karate fight, record stupid rap tracks, and generally act like swaggering idiots for over an hour. Step Brothers continues to be endlessly watchable and endlessly quotable — which is what a true comedy is all about.
6. Wedding Crashers (2005)
Image Source: Slash Film
Raucous and happily obnoxious, Wedding Crashers makes fun of cheaters and liars — ultimately celebrating a odd version of true love. The script follows two part animals approaching middle age who specialize in being uninvited nuptial guests in order to pick up women. Maybe more than any other genre, comedy relies on the cast. It needed the right actors to bring it to the next level. This film found it in leading men Owen Wilson and Vince Vaughn. It also found it in Rachel McAdams, the unusually multi-dimensional love interest to Wilson and Bradley Cooper’s perfectly portrayal of a sleazy fiancé. Together they take a great script and make it into a fantastic comedy.
5. Forgetting Sarah Marshall (2008)
Image Source: Writing to reel
The comedy genre was forever changed in the 2000s thanks mostly to Judd Apatow. With 40 Year Old Virgin being just the beginning, he went on to produce a number of similar comedies that helped shaped the genre. This included 2008’s Forgetting Sarah Marshall. For this film, Jason Segal mined his own personal life to write the ultimate breakup movie. Jason plays Pete Bretter, a composer for a CSI-like show starring his girlfriend, Sarah Marshall (Kristin Bell). When Sarah abruptly breaks up with him, Peter jets off to Hawaii to ease his sorrows. Cue the hilarious Paul Rudd, Jonah Hill, and Russell Brand. Combine an all-star ensemble cast with director Nicholas Stoller — with whom Apatow had worked with on various shows — and thus a modern romantic comedy classic was born.
4. Old School (2003)
Image Source: Movie Fone
The best college comedies deconstruct what college is really all about. When you’re in college, it’s stressful, expensive, and often bewildering. But a lot of people only remember the beers and party. When thirty-something Mitch (Luke Wilson) leaves his cheating girlfriend (Juliette Lewis) and moves into a house adjacent to a college campus, his friends (Vince Vaughn and Will Ferrell) decide to throw him a wild party in hopes to boost his spirits. The house however is zoned for students-only. In a not-so logical turn of events, the trio decide to make the house a frat house. Vaughn uses this brief return to college as a jump start to his mediocre life. Ferrell as “Frank the Tank” embraces it fully by streaking and mainlining beer. It’s unquestionably Ferrell’s breakout role. Old School continues to be one of the best college movies to date.
3. Borat: Cultural Learnings of American for Make Benefit Glorious Nation of Kazakhstan (2006)
Image Source: Page 6
I love Borat very much. I think it is one of the funniest movies of all-time. This isn’t because it is dumb, but because it is very smart. Was Sasha Baron Cohen exploiting his unsuspecting marks (boogied rodeo audiences, psycho gun merchants, unsuspecting news anchors, craven politicians) by pretending to be a dimwitted, bigoted Kazakh journalist on a journey though America? Sure. Borat has lost none of its punch as a laugh machine, in part because the humor often comes from deeply uncomfortable places. The film becomes harder to watch as the years pass by. And yet, somehow, it also becomes funnier.
2. Lady Bird (2017)
Image Source: NME
Greta Gerwig’s solo debut doesn’t get it’s laughs from cheap jokes or teen spewing dialogue so clever that it could only be written by a 50-year-old. It’s easy to make a movie about high school; its significantly trickier to make one that feels true. In this Sacramento high school circa 2002, Christine “Ladybird” McPherson (played by the amazing Saoirse Ronan) is fed with life in Sacramento and wish to move to the east coast where “the culture is.” Everything our heroine experiences in her senior year –from her bizarre teen Sondheim production to the mother-daughter dress shopping to stupid crushes and awkward sex — is hilariously relatable and incredibly touching.
1. Best in Show (2000)
Image Source: Collider
16 years after co-writing and starring in This is Spinal Tap, Christopher Guest made this other milestone mockumentary. Best in Show is a flawlessly executed work that transforms spoof into something completely sublime. The film makes fun of a Philadelphia dog show with every instrument in the satirist’s arsenal, from the skewer to the mallet. With Eugene Levy’s buck-toothed, two left-footed cuckold to Jane Lynch’s supe- competitive trainer, canines play straight men while their owners run amok. This movie is consistently just plain funny and sometimes ascends to a kind of crazed genius.