Bill Hader is one of the funniest and most memorable comedians ever, having dominated the 2000s and 2010s with roles in both hilarious comedies and serious dramas. Hader even tried himself out as a director/writer with his dark comedy series Barry, where he also plays the titular role.
Whether in a guest role or as a part of the main cast, Hader is charming and lovable and usually the best character in any movie. The most hilarious comedies starring Bill Hader are obvious markers of his talent, comedic timing, and memorable performance; they aren’t all comedies where he’s the lead, but they’re all the better because of his involvement.
10
‘Knocked Up’ (2007)
Directed by Judd Apatow
Knocked Up is one of those cult classic Judd Apatow comedies that’s as problematic as it is great. Apatow’s movies usually gather a similar, if not the same, cast, and Bill Hader is one of the actors that appears often. The comedy ensemble that includes Seth Rogen, Paul Rudd, Jason Segel, and Jonah Hill is often seen with Hader in some of his most hilarious movies.
Knocked Up follows Alison (Katherine Heigl), an ambitious newscaster who one day gets the promotion she’s been anticipating. To celebrate the promotion, she goes out, parties, and drinks, meeting Ben (Rogen), an ambitionless slacker. The two hook up for the night and part ways the next day. After several weeks, Alison realizes she’s pregnant and tracks down Ben to tell him. The movie follows them, their families and friends trying to bond while Alison carries the baby to term. The movie has plenty of hilarious moments and banter, and one of the most hilarious scenes is Hader’s impersonation of Jabba the Hutt when he’s talking about Alison’s puking on screen.
Knocked Up
- Release Date
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June 1, 2007
- Runtime
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129 minutes
9
‘Trainwreck’ (2015)
Directed by Judd Apatow
Trainwreck was directed by Judd Apatow, but it was written by Amy Schumer, and it’s the first feature film she wrote. Trainwreck was a lot of things and not very memorable overall, but the best part about it is Hader as the lead’s romantic interest. He portrays a funny, smooth-talking, clever orthopedic doctor who treats famous athletes; we’ve long waited for Hader to star as the romantic lead and Trainwreck gave us the satisfaction. He’s totally believable in it, and sometimes the best part in a lot of the scenes (though the ensemble cast does a pretty great job).
Trainwreck is about Amy (Schumer), a journalist with a drinking habit and a track record of wild behavior, who gets an assignment to write an article about sports doctor Aaron Conners (Hader). The moment the two meet, sparks fly, but Amy’s family life interferes with her personal choices and their relationship quickly turns rocky. With plenty of highlights, Trainwreck is funny and emotional, and it’s worth watching for, well, the already-named reason—Bill Hader.
Trainwreck
- Release Date
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July 17, 2015
- Runtime
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125minutes
8
‘Pineapple Express’ (2008)
Directed by David Gordon Green
Pineapple Express is one of the funniest stoner movies, with plenty of memorable lines and gags. It’s definitely one of Rogen and James Franco‘s best, but its array of colorful and wild characters deserves special recognition. Hader portrays the “tester” of the Pineapple Express strain of marijuana sometime in the distant past (portrayed in black and white), and it’s one of the best introductions to a movie. A lot of the scenes are very funny, but this sort of cold open into the Pineapple Express universe is one of the funniest.
The movie follows Dale (Rogen) and his marijuana dealer, Saul (Franco). Dale visits Saul, who gets his hands on the rare “Pineapple Express” strain; the two smoke it before Dale returns to work, but during his outing, he witnesses a murder in front of a crime boss’ home. Dale and Saul are pursued to be eliminated as witnesses, and the movie shows their escape and developing friendship. Pineapple Express was directed by David Gordon Green, and it has great cinematography, one of the best in a comedy like this one.
7
‘Hot Rod’ (2007)
Directed by Akiva Schaffer
Hot Rod is a project by The Lonely Island crew (Andy Samberg, Akiva Schaffer, and Jorma Taccone) and Schaffer’s directorial debut. This was a time when Samberg was on SNL, often together with Hader, and so their paths often crossed on film, too. Hot Rod is one of the most likable movies of the 2000s but also a highly underrated gem that feels like a cult classic in the making. It’s wholesome but also full of gags and brilliant slapstick comedy. The 2000s were a different time and the same things may not be funny to people today, but Hot Rod is bound to draw a chuckle out of most people.
The movie follows self-proclaimed stuntman Rod Kimble (Samberg), who wishes to perform the ultimate stunt—jumping over 15 buses—for charity. He gathers his childhood friends and brother and begins training for the stunt. Hader portrays Rod’s childhood friend Dave, who in one scene takes acid and trips while a piece of metal remains stuck in his eyebrow. Dave’s often spaced out, but he’s encouraging and honest with Rod when necessary. His most iconic line is “I was trippin’ b**ls, so I decided to get on my bench grinder.”
Hot Rod
- Release Date
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August 3, 2007
- Runtime
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88 minutes
6
‘Sausage Party’ (2016)
Directed by Conrad Vernon and Greg Tiernan
Sausage Party is an outlandish adult animation film that makes inanimate objects come to life, as if they’ve always been like that. Showing regular daily objects and food items as living beings is a trippy experience and can be a bit off-putting to people; this is potentially why the movie didn’t really receive much audience acclaim, though critics absolutely loved it. It features a stellar voice cast that includes Edward Norton and Salma Hayek, next to the “usual suspects” like Hader, Rogen, Nick Kroll, Danny McBride, and Kristen Wiig.
Sausage Party follows anthropomorphic foodstuffs populating the Shopwell Supermarket; they believe that shoppers who come and buy the items are gods that take them to a Great Beyond. The protagonist is a sausage called Frank (Rogen), who wants to see the Great Beyond with his hot-dog-bun girlfriend, Brenda (Wiig), and his best friends, sausages Carl (Jonah Hill) and Barry (Michael Cera). When their packages get purchased one day, the sausages and Brenda excitedly await life but realize the truth is much crueler than they had hoped for. Hader voices two characters: Firewater, an old Native American liquor bottle, and José Tequila, a Mexican bottle of tequila.
5
‘Tropic Thunder’ (2008)
Directed by Ben Stiller
Tropic Thunder is just one of the movies on this list that could never be made today but remains golden for its hilarious running jokes and extravagant characters. The movie is a satirical view of Hollywood and its clichés and tropes, including method actors willing to go as far as switching races (like Robert Downey Jr.‘s character, Kirk Lazarus) and high-functioning gag comedians addicted to drugs (like Jack Black‘s Jeff Portnoy). Tropic Thunder, no matter how much you hate it, has some of the funniest social commentary around.
Tropic Thunder follows the stars of a new war movie, Tugg Speedman (Ben Stiller), a washed-up action hero; Kirk Lazarus, an Australian method actor; and Jeff Portnoy, a cocaine-addicted comedian who wants to rebrand. Their shoot is overseen by the studio, headed by Les Grossman (Tom Cruise) and his right-hand man, Rob Slolom (Hader). When the shoot of the movie encounters problems, the three actors are left in the treacherous jungles with their castmates, and Slolom tries to keep the entire shoot together in an overzealous and chaotic manner.
4
‘Paul’ (2011)
Directed by Greg Mottola
Simon Pegg and Nick Frost co-wrote the sci-fi comedy Paul and star together as the two leads going to San Diego Comic Con. This nerdy comedy won people over with its brilliant jokes and the chemistry between the main cast, including the small alien Paul, who was voiced and portrayed in motion capture by Seth Rogen. This clash of the comedic worlds of the British and American scenes is one of the coolest and most likable comedies of the 2010s.
Paul follows Graeme and Clive (Pegg and Frost, respectively), two sci-fi and comic book enthusiasts who traveled from the UK to San Diego to go to Comic-Con. On their way there, they drive along the road where many UFO sightings have happened, collecting memories, until they encounter an actual alien posing as a redneck. They take the alien called Paul with them so he doesn’t get caught by the Secret Service. Bill Hader appears in the movie, too, and he portrays one of the agents pursuing Paul called Haggard.
Paul
- Release Date
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February 14, 2011
- Runtime
-
110minutes
3
‘Forgetting Sarah Marshall’ (2008)
Directed by Nicholas Stoller
Forgetting Sarah Marshall is another 2000s comedy that is unforgettable; it has so many great jokes, and it’s a sweet rom-com besides being a hilarious mess. Jason Segel is the lead, and he also wrote the movie himself, while it was director Nicholas Stoller‘s debut feature. Segel is joined by a funny array of cast members, including Kristen Bell, Mila Kunis, Jonah Hill, Paul Rudd, and Bill Hader. It’s a charming feature full of really wholesome moments, while at the same time pushing the limits of raunchiness.
Forgetting Sarah Marshall follows TV composer Peter, whose long-term girlfriend, actress Sarah Marshall (Bell), suddenly breaks up with him. Peter is desperate, so he decides to go to Hawaii to try to get over the breakup but realizes Sarah is in the same hotel with another man. While Segel is the undoubted star of the movie with his brilliant comedy chops, other actors stand out, too. Bill Hader portrays Peter’s stepbrother and best friend, Brian.
2
‘Cloudy With a Chance of Meatballs’ (2009)
Directed by Phil Lord and Christopher Miller
Though an animation aimed at all ages, Cloudy With a Chance of Meatballs is undoubtedly one of the most hilarious comedies of the 2000s (maybe even of all time). The quality of the jokes is everlasting, and there are many hidden moments of joy and laughter that can be rediscovered only when watched again. Cloudy also has one great ace up its sleeve, and it’s Bill Hader as the voice of the protagonist, the scientist Flint Lockwood.
Cloudy With a Chance of Meatballs follows Flint Lockwood, a young scientist who wishes to make a brilliant new invention. He’s distant from his father and shunned by the community as a weirdo, but finally manages to create a machine that turns water into food. His troubles begin when the machine becomes sentient and starts creating food storms; Flint has to stop it before it destroys his world, family, and friends. The relationships and the family dynamics in the movie are intricate and wholesome, and the comedy is quirky, leaning on slapstick very often. Some of the best parts include Officer Earl (Mr. T) squeezing one single tear back into his eye and every time Andy Samberg’s Baby Brent says “uh-oh” very loudly.
1
‘Superbad’ (2007)
Directed by Greg Mottola
The icon, the legend, the McLovin of teen comedies is, without a doubt, Superbad. This is a stoner movie, a buddy comedy, and a coming-of-age story about two friends who want one last chance at becoming legends in high school. Seth Rogen and Evan Goldberg wrote the script based on their high school experiences, even giving the protagonists their own names. Jonah Hill and Michael Cera portray Seth and Evan, but the standout of the movie is Christopher Mintz-Plasse, who plays Fogell, aka McLovin, who becomes a legend by the end of the movie.
Superbad shows two high school best friends, Seth and Evan, planning to lose their virginity at the house party thrown by Jules (Emma Stone), Seth’s longtime crush. Their plan is bombed by Fogell, who wants to come along and obtains a fake ID that he believes will help them get alcohol for the party and be irresistible there. However, his fake ID only says McLovin, but since the trio promised Jules alcohol, they scramble for a way to get it. Meanwhile, Fogell befriends two cops who are completely clueless and unserious, officers Michaels and Slater, played by Rogen and Hader.
Superbad
- Release Date
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August 17, 2007
- Runtime
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113 minutes