Ranking the Films of Judd Apatow From Worst to Best

Name a Hollywood comedy from roughly 2004 onwards and chances are Judd Apatow had something to do with it. Whether you love his tales of man-children learning to behave more like adults, or loathe his inability to make a comedy that runs at less than 120 minutes, one can't deny the man's enormous contribution to the Hollywood comedy machine as writer, director, producer, and everything inbetween.

Now the filmmaker behind Knocked Up and Trainwreck is back after a five-year-long directorial hiatus with The King of Staten Island, a comedy-drama based on the life of Saturday Night Live comedian Pete Davidson. But where, we ask, does his latest effort rank within his wider filmography?

6. This is 40 (2012)

Where to watch it: Various streaming services

Apatow had already mined aspects of his own life for Knocked Up's couple-in-crisis Peter and Debbie –– though this time there was a collective agreement he'd taken things a bit too far. This was billed as a “sort-of sequel” to Knocked Up, with Paul Rudd reprising his role as… well, Judd Apatow? Leslie Mann (Apatow's real-life wife) also stars, alongside his actual kids, which gave the odd effect of Apatow living out some weird and fantastical surrogate life through Rudd. It's intermittently funny, but aimless, though Megan Fox shines in a small role, and Mann is excellent.

5. The King of Staten Island (2020)

Where to watch it: Various streaming services

Apatow's latest is another portrait of a young and up-and-coming comedian: this time Pete Davidson gets the same deal Amy Schumer got in Trainwreck playing a fictionalised version of himself. Stylistically this film differs somewhat from the rest of the canon: the choice of Paul Thomas Anderson's regular DP Robert Elswit gives the picture an indie sensibility and genuine texture, but it still retains the baggy, almost anti-narrative of a conventional Apatow picture – perhaps to a fault. It's not his funniest film, either, and doesn't exactly mine the dramatic aspects for what they're worth. But Davidson is likeable enough, and the supporting cast – especially Bill Burr, Marisa Tomei, and Bel Powley – are great.

4. Trainwreck (2015)

Where to watch it: Various streaming services

Through films and TV projects like Girls and Crashing, Judd Apatow has carved out a side gig bringing lesser known comedians to the public consciousness. Case in point: Trainwreck, which gave Amy Schumer her biggest career boost to date in its telling of a sexually adventurous woman whose resistance to romance is jeopardised by an encounter with a charming sports doctor. Schumer is uniformly excellent here, but the MVP might be Bill Hader, who shines as an unlikely romantic interest. How is this five years old already?

3. Funny People (2009)

Where to watch it: Various streaming services

Apatow was perceived as entering a “Woody Allen phase” with this Great Gatsby-inspired Adam Sandler dramedy, which riffed on the actor's real life career and on-screen persona. But what seemed poised as a Sander comedy apology turned out to be nothing of the sort (he continues making bad movies, but Uncut Gems allows us to forgive all). The plot is surprisingly dour; Sandler's movie star is diagnosed with a terminal illness and given a few months to live. In the meantime, he befriends Seth Rogen's wannabe comedian, Ira, and the two become an unlikely duo. Critical reception at the time was lukewarm, but age has been kind to Funny People – smart, sensitive, and funnier than it was initially given credit for, with a top five Sandler turn.

2. The 40-Year-Old Virgin (2005)

Where to watch it: Various streaming services

Few films are really endlessly rewatchable, but something about Judd Apatow's breakthrough comedy has rendered it just so. Steve Carrell shot to fame playing loveable virgin Andy, whose attempts to have sex for the first time are rendered here as a series of wacky antics and awkward encounters. Some of the jokes really show their age, yet what really sings is the group dynamic, showcasing Apatow's talent for picking excellent secondary performers: Seth Rogen is excellent, but Paul Rudd feels like the standout. The result is something equally crude and sweet that basically came to define the Apatow brand, paving the way for a new era of filmic bromances.

1. Knocked Up (2007)

Where to watch it: Various streaming services

Pound for pound, this feels like the best weighed of all Apatow's directorial efforts, striking just the right balance between comedy and drama whilst retaining all the elements that make his films distinctly Apatowian. Seth Rogen gives his best performance (at least in an Apatow film) as slacker Ben, who winds up impregnating Katherine Heigl's E! News presenter, Alison, on a drunken night. Knocked Up was met with universal praise from critics and at the time was hailed as a kind of masterpiece; maybe overfamiliarity has dulled its impact somewhat here in 2020, but this still stands as a relentlessly entertaining and influential rom-com inversion that almost justifies its two-hour-plus length.

Artwork for this article was created by Braulio Kuwabara. You can follow his work here.