You cannot talk about comedy in the 21st century without mentioning Judd Apatow — the writer, director, and producer behind some of the most hilarious, heartfelt, and oft-quoted comedies ever made. Despite his multitude of skills, his most impressive might be his ability to identify and empower comedic talent. The sheer number of stars whose careers Apatow has launched is staggering. From Seth Rogen to Amy Schumer to Jonah Hill, he has consistently managed to get the most out of his collaborators.
It is not hyperbole to say Apatow, along with his merry band of jokesters, has fundamentally changed the comedy landscape over the past few decades, forcing everyone else to keep up. Here are the 10 best Judd Apatow movies, ranked from worst to best.
10. Wanderlust (2012)
You might not be as familiar with Wanderlust as the rest of the films on our list, but I advise you to change that as soon as possible. While this movie might not feature some of the more familiar faces in the extended Apatow Universe, it does feature Paul Rudd, so what else do you really need? Here Rudd plays George, a recently laid-off New Yorker married to Jennifer Aniston’s Linda. The story gets going when George and Linda are forced to leave New York and set out for the country, eventually winding up at Elysium, a bed & breakfast & new age commune. It’s in introducing the eccentric inhabitants of Elysium — headlined by an unrecognizable Justin Theroux as the group’s leader — that the film hits its stride.
This is very much an ensemble comedy and the hijinks that ensue work best when the gang – featuring longtime comedic actors like Alan Alda, Kathryn Hahn, and Jordan Peele – get to play off each other, a staple of Apatow’s brand of comedy.
9. The Big Sick (2017)
While not written or directed by Apatow, The Big Sick perfectly captures the balance of heart and hilarity that Apatow has mastered in the back half of his career. It also shows off his eye for talent, giving the then largely unknown Kumail Nanjiani the chance to write and star in his first film. A largely biographical movie, The Big Sick tells the story of Kumail’s time as an upstart stand-up comedian and the burgeoning relationship with his soon-to-be-wife Emily (Zoe Kazan). What starts as your typical rom-com fare quickly turns when Emily is hospitalized and eventually put into a coma.
Many of the film’s best moments come during the thorny, awkward, and charmingly misguided conversations shared between Nanjiani and Kazan’s parents, played wonderfully by Holly Hunter and Ray Romano. This is serious stuff to be sure, but Apatow and company inject enough comedy to make this a worthy entry on our list.
7. Step Brothers (2008)
Now we start to arrive at the heavy hitters. Step Brothers might just be the most quoted comedy of all time and with good reason. There’s no other way to put it — this movie is simply hilarious. By now you know the story: two adult children are forced to live together because their parents get married. Simple, yes, but with Step Brothers, Apatow was able to capture stars Will Ferrell and John C. Reilly, as well as writer/director Adam McKay, at the absolute peak of their careers, and empower them to make perhaps the silliest, most absurd comedy ever. The drum set, karate, and the fucking Catalina Wine Mixer!
6. Anchorman (2004)
In many ways, Anchorman is where it all started. While Apatow had been writing and producing here and there for years — including his now cult TV series Freaks and Geeks — this was the first movie officially released by Apatow Productions. And what a start it was. Will Ferrell has played dozens of characters over the years, but perhaps none more enduring than Ron Burgundy, the whiskey-swilling, cigarette-smoking, burrito-flinging host of San Diego’s Channel 4 News.
5. Bridesmaids (2011)
Bridesmaids made waves at the time for its refreshing and raunchy depiction of female friendship, something sorely lacking from the preceding decades of comedy, but this movie ultimately transcends any classification. Writer and star Kristen Wiig leads a comedy so spectacularly ludicrous that you need only a few words to bring to mind its most hilarious scenes: the dress, the chocolate fountain, the airplane. Also of note is the cast, which includes such comedy heavyweights as Maya Rudolph, Melissa McCarthy, and Rebel Wilson.
4. Pineapple Express (2008)
While this might not be the highest film on our list, it surely is the highest. Pineapple Express marks the second collaboration between Apatow and writing and directing duo Seth Rogen and Evan Goldberg, following up 2007’s smash hit Superbad, and plays with similar themes of male friendship and mad-cap adventure. Of course, this time the protagonists are well-past high school and are extremely high the entire time. That said, Seth Rogen and James Franco make an as good, if not better, comedic duo as Jonah Hill and Michael Cera, while somehow finding themselves in far more absurd and violent situations than the latter could have ever imagined.
3. Forgetting Sarah Marshall (2008)
For all his varied abilities, Apatow might be most at home within the rom-com, a genre he plays with consistently and to great success. Starring Freak and Geeks alum Jason Segel as a recently dumped Peter Bretter, Forgetting Sarah Marshall finds catharsis in both heartache and hilarity, forming an intriguing love square between Segel, Mila Kunis, Kristen Bell, and Russell Brand. Add in the incredible Hawaiian scenery and cameos from the likes of Bill Hader and Jonah Hill, and you have one of the best romantic comedies of the last twenty years.
3. Knocked Up (2007)
Speaking of romantic comedies, Knocked Up ranks up there with some of the most accomplished of all time. The story of the unlikely romance and unplanned pregnancy of couple Alison (Katherine Heigl) and Ben Stone (Seth Rogen) raked in $219 million at the box office, becoming a certified hit and one of the most surprising films of 2007. Introducing the stoner charm that would become his forte, Rogen is especially impressive here, slowly transforming from hapless loser to at least semi-competent partner and, eventually, father.
2. The 40-Year-Old-Virgin (2005)
The 40-Year-Old Virgin is a movie with a premise that doesn’t really sound like it should work. The story of a man approaching middle age who’s never slept with a woman receiving help from his co-workers to finally get laid could have easily slipped into lewd and problematic territory, but is instead one of the most purely joyous comedies of all time. That’s not to say this isn’t plenty raunchy, but the heart at its center, as well as Steve Carell’s charmingly dorky performance, do much to balance the scales. This, perhaps more than any other Apatow production, utilizes improvisational comedy, allowing the actors to riff each other before landing on the final result.
1. Superbad (2007)
Superbad is a movie that will likely top a lot of lists. Best comedy of the 21st century? Best coming-of-age comedy? Most quoted movie of all time? You’ll find no argument from this writer. Superbad, to put it bluntly, is a near perfect film and an excellent encapsulation of why Apatow is such a brilliant movie maker. Written and directed by Seth Rogen and Evan Goldberg, Superbad stars Jonah Hill and Michael Cera as, essentially, younger versions of the film’s creators: young, inexperienced high-school underdogs determined to have a night to remember. In that, they surely succeed, though not in the way they imagined.
Perhaps no comedy in history has pulled off the high-wire act of hilarity and sentimentality that this story of friendship and young love is able to walk.