It's time for a crash course in some cringe-comedy classics.

Judd Apatow has hosted the Directors Guild Awards multiple times over the years (sailing through the tough gig like he owned it). But somehow, Apatow is more than just a director. From TV's Freaks and Geeks on, he's launched what feels like an entire generation of onscreen comedy stars. And as a producer — of everything from Lena Dunham's Girls to Adam McKay's Anchorman — he's made as much of an impact in shaping and supporting the work of others. But Apatow does have his own movies, a little over a handful to date, and they're as pure an expression of everything he does well. Most are worth seeing. Here's our highly opinionated ranking of them, from worst to best.

The Bubble
Credit: Laura Radford/Netflix

7. The Bubble (2022)

Okay, this one's not so hot — blame it on the lockdown, a comedy killer — but it nonetheless bears some of Apatow's signature, including the redemptive onscreen presence of Leslie Mann, his wife. Dinosaur VFX not being this director's forte, Apatow loses the thread in moments when The Bubble goes big, plus his insights into Hollywood's vanity would have felt dated 30 years ago in The Player. Still, give him credit for doing more during the pandemic than binge-watch Mare of Easttown in his sweatpants.

The King of Staten Island
Credit: Mary Cybulski/Universal Pictures

6. The King of Staten Island (2020)

Somewhat overshadowed by its dawn-of-the-pandemic release (two festival launches had to be scrapped), Apatow's outer-borough comedy was the couch watch that kept on giving. The script derives from Pete Davidson's real-life backstory, at least partially, and, as a dramatic anchor, he's never been more impressive than he is here. But the movie's deeper charms are on the periphery: a believably blue-collar milieu, and a mighty performance by Marisa Tomei that should have received more awards traction.

Seth Rogan, Adam Sandler, ... | FUNNY PEOPLE Adam Sandler, Seth Rogen, and Jonah Hill raise their glasses
Credit: Tracy Bennett

5. Funny People (2009)

Daringly abrasive, this is the Apatow movie that feels least like a comedy — which isn't to say it isn't valuable on its own terms. Funny People is about the health scare of a superwealthy former stand-up comedian and movie star (someone very similar to lead Adam Sandler). As with Uncut Gems and Punch-Drunk Love, it illuminates Sandler's smarter instincts; he's always been underrated. Cutthroat competition is the film's theme, along with a vein of camaraderie. A cameoing Jason Schwartzman embodies your punchable, professionally successful frenemy.

Film Title: Trainwreck
Credit: Mary Cybulski/Fox

4. Trainwreck (2015)

Like The King of Staten Island, this one also has autobiographical roots, in star-writer Amy Schumer's ping-ponging party-girl days. But Schumer isn't after microscopic accuracy, and, working with Apatow (a keen script developer), Trainwreck blooms into something more universally relatable. Colin Quinn is the film's dramatic surprise as a difficult dad on the decline, and the mercurial Tilda Swinton steals the movie in her scenes as a glib magazine editor.

9. Knocked Up (2007)
Credit: Suzanne Hanover/Universal Pictures

3. Knocked Up (2007)

Bad blood between star Katherine Heigl and Apatow eclipsed this pregnancy comedy's merits — a shame because everyone should have benefited from what works beautifully, especially the interplay of the actors. Apatow's self-penned script is a critique of undeveloped boy-men, not a celebration of them, yet, the more you examine the central relationship, the flimsier it seems. (The movie also became a piñata in an external debate about issues of reproductive choice, something Apatow should have anticipated.) Still, rom-coms come flimsier, and most of them aren't this self-reflective.

This Is 40
Credit: Suzanne Hanover/Universal

2. This Is 40 (2012)

This marital anxiety comedy set the tone for much of the director's work to come: personable, actor-centric, and pleasantly meandering. (Something you learn when watching Apatow movies: Plot is overrated.) Technically, it's a spin-off for Mann and Paul Rudd's characters from Knocked Up, but the material is less about accidental families than the ones kept together by hard work, compromise, and lots of screaming. Apatow's real-life daughters Maude and Iris come into their own.

Jane Lynch, Steve Carell, ... | There are two things Paula wants: Andy to be her ''f--- buddy,'' and enough weed to keep her baked for a week.
Credit: Suzanne Hanover

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

An essential aughts comedy and one of the most confident feature debuts ever, The 40-Year-Old Virgin delivers Apatow's cringe-comedy elements to the big screen intact. Steve Carell and Catherine Keener have an awkward yet believable rapport that would shame most "serious" dramas, and, once again, Apatow fills the margins with rich details: an iconic chest-waxing scene, Paul Rudd's lovestruck dumpee, Jane Lynch's intimidating boss, and Leslie Mann again pocketing her husband's film — this time as a near-hookup. It's definitely the place you should start with Apatow's work, even if his movies have become more complex.

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