30. BAD SANTA (2003)
Vulgar drunks are nothing new in comedy, but Bad Santa pierces the taboo of subjecting an innocent child to such behaviour, and the raunchy result takes the About a Boy formula and throws in a bunch of firecrackers. Oscar-winner Billy Bob Thornton plays the alcoholic misanthrope in question, employed as a mall Santa, unflinchingly awful in everything he does in front of nine-year-old Thurman Merman (Brett Kelly). (Bonus points for paving the way for caustically cruel comedies like Bad Words and Observe and Report.)
29. RUBBER (2011)
If ever there were a movie where the premise betrayed how brilliant and funny a movie it was, it’s Rubber. Would you want to see it if I told you it was about a tire named Robert that inexplicably comes to life, rolling around and exploring the world, before discovering its ability to psychokinetically blow up people’s heads, leading to a serial killing spree by the self-aware wheel covering, with a troop of police officers hot on his trail — all viewed by a group of commenting spectators sitting in lawn chairs on the side of the highway and watching through binoculars? How about if I told you it was the most clever comedy of the last decade? Both are true.
28. FORGETTING SARAH MARSHALL (2008)
What started off looking like nothing but a sitcom episode blown full-length became instead one of the most emotional and sincere comedies of the new millennium. Jason Segel instantly makes the leap from supporting actor to lead with his role of the dumped Peter, watching his celebrity ex-girlfriend (Kristen Bell) happy with her new lothario lover, rock star Aldous Snow (Russell Brand, in the role that made him a star overnight), from the convenient location of an awkwardly adjacent villa at a Hawaiian resort. (Bonus points for being the debut of Nicholas Stoller, who’d go on to direct Neighbors and its sequel.)
27. DEATH AT A FUNERAL (2007)
No, not the Chris Rock one. The original Death at a Funeral is a British farce revolving around a funeral being arranged by Daniel (Matthew Macfadyen) for his father, with everything possible going wrong. The scene-stealing highlight is Alan Tudyk as the American fiancé of Daniel’s cousin; nervous about meeting the family for the first time, he takes what he thinks is Valium but turns out to be acid. Peter Dinklage also does a great job with an underwritten twist of a role — oddly, the same character he’d oddly go on to play in the American remake three years later. Director Frank Oz is no stranger to brilliant comedy, having helmed Dirty Rotten Scoundrels, In & Out, and Bowfinger, but Death at a Funeral is his best.
26. STATE AND MAIN (2000)
Comedies about Hollywood and moviemaking always run the risk of coming off too inside-baseball; even Robert Altman’s The Player, considered the golden (non-musical) standard of Hollywood comedies, has more than a few references bound to go over Joe Sixpack’s head. And State and Main does come off feeling like The Player at times, but with the speed turned up. Written by wordsmith David Mamet at the speed of a Neil Simon play retold by Aaron Sorkin, State and Main‘s barbs and backhanded insults fly fast and furious, not caring if you miss a joke because you’re too busy laughing at the previous one, all while mercilessly skewering the ridiculous world of filmmaking.
25. OBSERVE AND REPORT (2009)
Writer-director Jody Hill has only directed two movies. The first, The Foot Fist Way, was the calling card that got him invited to Hollywood by Will Ferrell. The second, Observe and Report, is what he made once inside: an insanely subversive “comedy” that focuses on a mall cop as mentally unstable as Taxi Driver‘s Travis Bickle — and just as likely to explode in unpredictable violence once their fuse inevitably burns out. Ronnie Barnhardt (Seth Rogen) is the head of security at a shopping mall who leads an untethered hunt for a streaker that exposes himself to the jewellery store employee Ronnie’s in love with, Brandy (Anna Faris). After Rogen’s established stoned-teddy-bear persona in The 40-Year-Old Virgin and Knocked Up, the general public reacted to Observe and Report the same unfair way they did to Jim Carrey’s dark The Cable Guy a decade earlier. It also got lost in the shadow of Paul Blart: Mall Cop, but they couldn’t be more different. One is the greatest black comedy of the last 20 years; the other stars Kevin James.
24. THE HANGOVER (2009)
Yes, it’s just an adult Dude, Where’s My Car?. Yes, it’s the same premise of few guys waking up after a crazy night in a trashed place and having lost something important, who have to retrace their previous night’s escapades to piece together the mystery only to find the item back where they started. But the inescapable fact is The Hangover reheats a previous comedic premise to an even better temperature, balancing out the ingredients while it’s at it and throwing in a few sublime touches (like Ed Helms’ out-of-nowhere piano ballad about tiger dreams). The result is a movie both comfortingly familiar and brazenly funny.
23. SHAUN OF THE DEAD (2004)
The movie that introduced Simon Pegg to the world (not to mention director Edgar Wright, who’d also make one of 2017’s best movies and land himself again at #15 on this list) came at a time when supernatural movies were starting to get into a well-worn groove, including zombie flicks. Shaun of the Dead climbed above the many genre comedies of the time by walking the delicate tightrope left by The Princess Bride: being both a clever, funny parody of zombie movies and a suspenseful, gory zombie movie in its own right. Follow-ups from Wright, Pegg, and Nick Frost Hot Fuzz and The World’s End did the same with cop and alien movies, with diminished results, but Shaun of the Dead feels as fresh (and funny) today as it did in 2004.
22. CLERKS II (2006)
When more than a decade passes between an original and a sequel, it’s usually for one of two reasons: either the people behind it need more money or they waited until they had a really good idea for a second movie. While there may have been an element of writer-director Kevin Smith returning to his comfort zone for another go around with clerks Dante (Brian O’Halloran) and Randal (Jeff Anderson), what makes Clerks II such a bold movie is its willingness to explore such heavy concepts as the deep love underlying lifelong male friendships, the casualties a romantic relationship can leave in its wake, and the life dissatisfaction ’90s slackers began coping with in the 2000s. In its own ways, it’s just as brilliant a comedy as 1994’s Clerks. And that’s before you even include the out-of-nowhere Jackson 5 and Q Lazzarus dance sequences.
21. BRIDESMAIDS (2011)
9 to 5. Clueless. Means Girls. Every one was treated as an anomaly because of the backwards belief female-led comedies aren’t funny. Bridesmaids is yet another blisteringly effective argument against such brainless thinking, balancing emotions and poop jokes just as well as the boys. Blending the Judd Apatow school of comedy with her SNL experience, Kristen Wiig plays Annie, a thirty-something without much going on in her life beyond her friendship with her childhood BFF, Lillian (Maya Rudolph). When Lillian gets engaged, it slowly spins Annie’s life out of control. Not only did Bridesmaids give Wiig carte blanche to pick her own projects thereafter, it made a movie star out of Melissa McCarthy. But most importantly, it’s just damn funny.