When Anchorman: The Legend of Ron Burgundy premiered 20 years ago, it wasn’t necessarily a game-changer for Will Ferrell, at least not in terms of his movie stardom. If anything, its existence was proof that Ferrell already had the juice; the previous year, the successes of Old School and Elf put him on the Hollywood fast track, and his dream project with collaborator Adam McKay was one for him. But for producer Judd Apatow, it was arguably more of a milestone. Apatow had been in the entertainment industry for well over a decade, and during that time worked on a number of great projects (mostly TV shows). But Anchorman was his first hit movie as a producer, which ultimately became more important to his career than his writing or directing (though he’d go on to yield plenty more hits that way, too). A very silly, gag-packed yet idiosyncratic comedy about male vanity in 1970s San Diego kicked off a 10-year period where Apatow became an influential and frequently star-making comedy guru, getting several of his own projects off the ground while — perhaps more importantly — helping any number of men and women find their cinematic and TV voices.
As a whole, the Apatow Project can appear somewhere between meta and navel-gazing, with so many movies and TV shows about people struggling on the fringes of creative industries, attempting to become functional adults. This also makes his producer’s stamp, on projects that likely have little to none of his personal experience in them, unusually auteur-like, as he goes from scrappy comedy writer working for his idols to de facto father figure, guiding younger performers through the process of growing up onscreen while still making his own mistakes. In some of his best projects, the characters aren’t performers or comedians at all. But comedy and performance still tend to be important to them, whether it’s geeks worshiping Bill Murray, best friends doing endless riffs for each other’s amusement, or the ridiculous demonstrations of masculinity or femininity that make up so much of adult life. Though Apatow’s influence seems to be waning these days, he’s still a major name in comedy, and the sheer number of projects he’s worked on over the years — before and after that Anchorman moment — is astonishing. Here, then, we have sorted through Apatow’s CV to rank all of those projects, from the mandatory masterpieces to the worthwhile curiosities to the intensely skippable misfires.
52. Celtic Pride (1996; writer and executive producer)
Among comedy nerds, this movie may be best-known for its status — as of 2010, anyway — as the only Judd Apatow-related movie Bill Murray had ever seen, and therefore his reason for avoiding Apatow’s calls (presumably to play the dad of a younger comedian in one of his movies, a la Harold Ramis or Albert Brooks). While Murray might do well to dip into something in our top 10 or 20, it’s hard not to laugh at the exacting cruelty of this judgment. Does it fit the crime of writing a goony comedy where two obsessive Celtics fans (Daniel Stern and Dan Aykroyd) kidnap another team’s star player (Damon Wayans) to throw the finals? Maybe not, but there’s definitely a spec-script-gone-wild element to this stretched-thin premise, cooked up by Apatow with future Weekend Update anchor Colin Quinn (who shares a story-by credit; Apatow has sole screenplay credit). Today, it plays almost like an alternate-timeline version of an Apatow movie, more concerned with loser bros who stay losing rather than figuring out the messy business of growing up. Luckily, Apatow himself did. — JH
51. The Bubble (2022; co-writer, director, producer)
It sounded exciting: Inspired by quarantine, Apatow would co-write and direct an ensemble comedy about the making of a big-budget movie within a peak-pandemic “COVID bubble” that quickly goes as wrong as possible. An eclectic cast who hadn’t appeared in many other Apatow projects (Karen Gillan, Pedro Pascal, David Duchovny, Keegan-Michael Key, Fred Armisen), a milieu that seemed prime to satirize Hollywood rather than just making it a default backdrop and a return to broader comedy after the dramedy of King of Staten Island, all with Netflix-funded carte blanche… it sounded almost too good to be true. And it was. The Bubble is a smidge better than its reputation, by virtue of having some laughs as opposed to zero. It’s also Apatow’s worst feature as a director, in a walk — one where rather than returning to his sketch-comedy and improv roots, he seems to mostly just forget everything else he’s learned about crafting a feature-length narrative. That would be fine if more of the jokes landed, but of this movie’s endless 126 minutes, maybe 15 or so are sufficiently amusing. – JH
50. Internet Ephemera (Vanity Fair: The 1990s; I Am Harry Potter; The Hills with James Franco and Mila Kunis)
Are these YouTube videos from various points in the aughts funny? Sure. By and large, they see Apatow playing straight man to someone else, whether he’s teeing up Maria Bamford by feeding her various ’90s touchstones to riff on for Vanity Fair, asking Daniel Radcliffe to clarify his belief that he actually is Harry Potter in a Funny or Die video or simply having James Franco and Mila Kunis recreate a scene from The Hills to drive home the important role TV writers play during the 2007 writer’s strike. They’re not the kind of thing you’re necessarily going to go back and revisit, and they’re not particularly emblematic of the rest of Apatow’s work, but they’re a perfectly fine way to kill a few minutes. — BS
49. “Bart’s New Friend” (Simpsons episode, 2015; credited writer)
Maybe it’s a little weird to single out a Simpsons spec script from a 22-year-old Judd Apatow that the show dusted off and did its customary group rewrite on in 2015, given that his contribution to contemporaries of the show further up this list are treated more broadly. But the other high-profile, pre-existing shows that Apatow worked on had more of his input for a longer period, while his Simpsons contribution was truly a one-off that, at the time, failed to get him so much as an interview (though he did join The Critic, from two of that show’s writers, some years later). Circa 2015, the gimmick about this installment was that Apatow conceived it in the show’s first, most grounded season, but there’s not much sign of that left in the premise, jokes, or meandering plot, beyond the core emotional hook of Homer getting hypnotized into thinking he’s a 10-year-old boy, and therefore becoming Bart’s best friend. Thematically compatible with Apatow’s tales of male regression, for sure, but not a particularly strong Season 26 outing for The Simpsons. – JH
48. Drillbit Taylor (2008; producer)
In retrospect, it’s hard to believe a dud like Drillbit Taylor was released just one year after Superbad. Both written by Seth Rogen, they couldn’t be more different: The former feels like a desperate bid to recapture the instant-classic magic of Superbad by repeating its formula — a trio of high-school misfits consisting of one loudmouthed chubby kid, one awkward gangly kid and one squirrely weirdo try to improve their social standing — but it does so with none of the humor or charm of its predecessor. For all its gross-out gags, Superbad was actually incredibly sweet, at its core a heartwarming coming-of-age tale whose male protagonists declare their love for one another and boop each other’s noses. Drillbit Taylor, on the other hand, feels incredibly mean-spirited, one whose actual premise is “a group of teens hire a homeless guy to be their bodyguard and protect them from bullies, but he and his homeless friends decide to plot to rob the kids instead.” Is there a climax where Owen Wilson beats up a kid after confirming he’s 18 and no longer a minor? Yes. Are any lessons learned? I dunno, I guess? It’s not worth watching to find out. — BS
47. Begin Again (2013; producer)
Given how immersed he is in the art and craft of comedy, it’s kind of touching that Apatow, still around the peak of his producing power, lent some of his cache to John Carney’s follow-up to the lovely indie sensation Once. Like that movie, it’s about two earnest souls bonding over music-making (Mark Ruffalo as a disillusioned record exec; Keira Knightley as a gifted songwriter). Unlike Once, Begin Again is kind of gash. Carney tends to work at about an every-other hit rate, and Apatow caught the off-rhythm entry in between Once and Sing Street. The movie, even at its weakest, is too close to Carney’s other work to suspect any kind of tampering in either direction from its most famous producer; chalk this one up to good taste and bad luck. – JH
46. May It Last: A Portrait of the Avett Brothers (2017; director, producer)
Filmed as the North Carolina band of brothers were recording their 2016 LP True Sadness, May It Last is a perfectly fine document of a specific moment in The Avett Brothers’ career — one where they’re trying to juggle fatherhood with headlining shows at Madison Square Garden and rubbing elbows with the likes of Apatow and super-producer Rick Rubin. The only catch? Everyone loves each other and gets along, there’s no stereotypical rock-star excess, and the record, not exactly a major departure for them sonically, is a commercial and critical success. In other words, there’s none of the typical conflict that drives the best music documentaries. It’s clear that Apatow is a big fan of the Avetts — but you pretty much have to be one too in order to get much out of this. — BS
45. Failed pilots and TV projects, including but probably not limited to North Hollywood, The Road Warriors, Class Clowns, The TV Wheel, Sick in the Head and Life on Parole (throughout 1990s; writer/producer)
In between staffing and/or creating some of the most acclaimed TV comedies of the ’90s and early ’00s, Judd Apatow tried to get project after project after project off the ground, experiencing plenty of failure to launch, dovetailing with his creative successes. Some of the pilots for these would-be series are lost to the sands of time; others provide a glimpse into a strange alternate history of its key players. For example, North Hollywood, a series that failed to launch circa Undeclared, would have featured Jason Segel, a pre-stardom Kevin Hart, a just-barely-pre-SNL Amy Poehler and a pre-Mad Men January Jones as struggling actors in Los Angeles. (It also features a scene that pre-visions the famous “a voice of a generation” scene from the first episode of Girls.) Poehler also appears on Sick in the Head, the pilot of which aired on cable a few times but is currently hard to find; meanwhile, you can sample the entire first episode of The TV Wheel, a truly bizarre sketch-comedy experiment starring Joel Hodgson from Mystery Science Theater 3000. If allowed to continue, some of these projects might have ultimately developed into cult favorites, though based on available evidence, it’s hard to picture any of them outshining the best work their various participants would go on to do instead. – JH
44. Judd Apatow: The Return (stand-up special, 2017)
Stand-up is obviously an art form near to Apatow’s heart. He started doing stand-up at 17, studied comics he admired, worked at various clubs, organized various comedy nights, and though he never made it as a stand-up in his own right, he went on to write for, learn from, work with and sometimes bring out the best of a whole bunch of great comedians. The experience of watching him actually perform stand-up, though, in this special literally decades after he first tried it, is an eerie one. His jokes are often pretty good, and his delivery is confident. There are laughs. Despite the fact that he and his wife and children are all, to some degree, famous people, much of the material is relatable enough, about binge-watching TV shows, following his family of women around Sephora and feeling despair over Trump’s presidency (still a fresh topic when the special was released). Yet there’s something both sweaty and prefab about his routines — as punchy as they are, there isn’t much drive behind them. It feels, curiously, like an exercise, like something Apatow needed to show he could do. He could — but no one’s really confused about why this wasn’t the first of many Apatow stand-up hours. – JH
43. Please Don’t Destroy: The Treasure of Foggy Mountain (2023, producer)
There are definitely some things to laugh at in this Goonies spoof from the trio behind Saturday Night Live‘s digital shorts: Narration by John Goodman. Bowen Yang as a deranged cult leader. Conan O’Brien as the exasperated father of Ben Marshall, who in real life is the only member of the group without a famous comedy writer for a dad. It’s silly and mildly enjoyable, but ultimately it feels like it could have just as easily been one of the five-minute shorts Please Don’t Destroy has made its calling card instead of a full-length feature. — BS
42. Heavyweights (1995; co-writer and executive producer)
Fun fact: The first big Judd Apatow production to make it to the big screen came courtesy of the Walt Disney company. Heavyweights comes from the days when Disney regularly made PG-rated, kid-targeted live-action comedies, and it’s not just a writing credit for Apatow; he co-wrote it with director Steven Brill, who went on to make a number of movies with mutual friend Adam Sandler, and reunited with Ben Stiller, who plays a supporting role. Anticipating his preening taskmasters from Happy Gilmore and Dodgeball, Stiller plays the new head of a camp for overweight kids, who attempts to transform it from a be-yourself summer haven into fodder for his fitness infomercials. Naturally, the kids and counselors fight back. Heavyweights approximates an early kid version of the Apatow style: Goofy underdogs who don’t look like typical movie heroes, depicted with some genuine, joshing sweetness. It’s also kind of a structural mess that lacks forward momentum or big laughs. Still, it’s an interesting curiosity as the only Apatow-penned movie on Disney+. – JH
41. The TV Set (2006, producer)
There have been a million satires made about Hollywood — it’s an industry that loves nothing more than to navel-gaze — but this 2006 David Duchovny movie written and directed by Jake Kasdan, who worked with Apatow on Freaks and Geeks and Undeclared and would later go on to direct Walk Hard, fails to stand out. That’s primarily because it’s entirely predictable in its cynicism. Oh wow, the network prefers the talentless hack to the more serious actor for the lead role? Whoa, and after those same network execs insist that our hero reshoot a version of his pilot that cuts out a character’s suicide because it’s “too depressing” and he purposely edits their version to be as bad as possible in an effort to tank it, the test audiences actually prefer the dumb and bad version? No way. — BS
40. Pee-Wee’s Big Holiday (2016, producer)
There’s always been a lot of talk about the “man-child” protagonists at the center of most Apatow flicks, but perhaps there’s no character who better embodies that term than Pee-Wee Herman. Co-written by Paul Reubens and Love‘s Paul Rust, this 2016 Netflix movie marks the deeply beloved yet deeply weird children’s character’s final onscreen appearance. (Reubens died of cancer in 2023.) Are we supposed to laugh when the movie refers to “a boy” trapped in a well and the boy turns out to be Pee-Wee, played by a then-64-year-old Reubens? Probably. Is Pee-Wee romantically interested in Joe Manganiello (playing himself here), who invites him to his birthday party in New York City and thus sets off our hero’s entire cross-country trek? That’s a little more open to interpretation. But aren’t we all? — BS
39. Kicking and Screaming (2005, producer)
Most of Apatow’s Will Ferrell movies are his top-tier collaborations with Adam McKay, but in between Anchorman and Talladega Nights, he slipped in this flimsy, family-friendly vehicle that feels more like something fellow Apatow pal Adam Sandler might have tackled around this time. Ferrell coaches a kids’ soccer team and squares off against his ultra-competitive dad (Robert Duvall). Also he gets addicted to coffee. That’s about it. Not really worth stealing the title of Noah Baumbach’s all-timer post-grad comedy for, is it? At the same time, it’s a harmless little sport-com that must have given Apatow some practice producing a comedy for normies. Then 40-Year-Old Virgin came out a few months later and changed everything. – JH
38. Funny or Die Presents (2010-2011; co-creator and producer)
In what now feels like a bizarre relic from a different age, Funny or Die, a sketch-comedy website that was co-founded by Apatow’s old pals Will Ferrell and Adam McKay, did well enough on the internet that they decided to… put it on cable?! There was, believe it or not, some kind of vague legitimization effect in making this scrappy-looking web enterprise into a “real” TV show (on HBO, the most prestigious TV outlet in existence at the time). As for the quality, well, it’s nothing that will replace Mr. Show or Kids in the Hall in anyone’s hallowed memories of watching sketch comedy on pay cable. For the most part, it’s a bunch of novelty acts with the welcome freedom to mess around (and, yes, sometimes bomb), a potpourri of ex-SNLers and castoffs from more niche (but also better) sketch shows like Human Giant. It feels most Apatow-like in the sense that he hadn’t really done sketch comedy in years at this point. – JH
37. Fun with Dick and Jane (2005, co-writer)
Screenplay credits, especially divided among multiple writers or teams, are hardly a guarantee of real authorship. That seems especially true of a movie like the 2005 version of Fun with Dick and Jane, which is a remake of a 1977 comedy already credited to four writers, and — according to an L.A. Times article — employed an all-star list of big-name screenwriters including David Koepp, Ed Solomon, Ted Griffin, Peter Tolan and a trio of Seinfeld alumni. Somehow, it was Judd Apatow and frequent collaborator Nicholas Stoller who wound up with their names on the script (alongside one of the original movie’s writers), though accounts of the film’s making suggest that it was heavily rewritten (and reshot) well into production. This is all to say that Fun with Dick and Jane is a consistently amusing if minor Jim Carrey vehicle that feels, if anything, vaguely more Stoller (who made the Neighbors movies) than Apatow; Carrey and Téa Leoni play a husband and wife who bumble into a life of crime when economic shenanigans leave them near-destitute, and it’s easy to imagine Seth Rogen and Rose Byrne getting up to similar antics a decade later. — JH
36. 30 for 30: Doc & Darryl (2016, co-director, producer)
Apatow’s Mets fandom is well-documented, so it’s not entirely unheard of that he’d co-direct ESPN’s 30 for 30 episode about two of the most talented members of that 1986 World Series-winning team, Darryl Strawberry and Dwight “Doc” Gooden. (Of course, Apatow’s touch is felt almost immediately when Jon Stewart and Bill Maher turn up among the doc’s talking heads.) Doc and Darryl is, by and large, a poignant look at what might have been, recounting the ways in which both star players’ careers were derailed by struggles with addiction. Their other controversies are given significantly less attention — to his credit, Strawberry addresses the domestic violence he committed at the height of his substance abuse candidly albeit briefly, saying, “I hauled off and hit her. I did. I was sick.” But it feels like Apatow and co-director Michael Bonfiglio do their best to breeze past the 1992 gang-rape allegation against Gooden and two other Mets. (Gooden denies raping the woman, claiming instead that he and his teammates had consensual sex wth her.) In fact, Gooden proves to be a much more challenging subject here; while Strawberry has turned his life around and stayed sober for decades, the 1985 Cy Young Award winner admits in the doc that staying clean is more like “a minute-to-minute thing” for him, and he was arrested for cocaine possession and driving under the influence as recently as 2019. If anything, it’s a harrowing reminder that these stories don’t always have easy, happy endings. — BS
35. Various stand-up specials for other people (producer)
How much of a creative impact does a producer really have on a stand-up special? Can we really give Apatow credit for the success (or lack thereof) of the specials he produced for other comedians? Well, that depends. In some cases, as with Tom Arnold’s The Naked Truth specials, Apatow is also credited as a writer. But even when he’s not contributing jokes, as is the case with specials he’s produced for Jim Carrey, Roseanne Barr, Chris Gethard and Jerry Seinfeld, it’s clear that he’s a student of the genre, one who learned how to turn someone else’s set into a well-received special long before he was a comedy kingmaker. — BS
34. Bros (2022, producer)
Regardless of whether or not you truly consider it to be “the first gay rom-com by a major studio” (Fire Island would like a word), this Billy Eichner vehicle was groundbreaking for casting all LGBTQ+ actors in its principal roles (even the heterosexual characters) and allowing its gay leads to do everything we’ve come to expect from straight couples onscreen — specifically, have sex — instead of chastely holding hands like they do in Hallmark movies. Unfortunately, it failed to connect on a broad level at the box office. Was that because, as Eichner put it, “straight people just didn’t show up for Bros,” or was it because at its core it’s a surprisingly paint-by-numbers Apatow film where the protagonist falls in love, self-sabotages, realizes some important truths and gets their life in order only to win their love interest back in the final act with a humiliating grand gesture? Probably a bit of both. — BS
33. Juliet, Naked (2018, producer)
Given that it’s an adaptation of his 2009 novel of the same name and deals with a lot of the same musical obsession as High Fidelity, Juliet, Naked is much more a Nick Hornby movie than it is a Judd Apatow one. But it does feature two semi-frequent Apatow collaborators in Chris O’Dowd (Bridesmaids, This Is 40) and Rose Byrne (Bridesmaids, Get Him to the Greek) who both completely understand the assignment and deliver engaging performances as an insufferable music nerd obsessed with the reclusive Tucker Crowe (Ethan Hawke) and his long-suffering girlfriend who eventually meets and falls in love with the man of her boyfriend’s dreams. — BS
32. The King of Staten Island (2020, co-writer, director, producer)
The King of Staten Island is significantly darker than most Apatow fare — it’s one of the few items on his IMDb page that frequently gets described as a “dramedy” rather than a straight-up comedy — but that’s due largely to its autobiographical nature. Pete Davidson, who co-wrote the movie, stars as a very lightly fictionalized version of himself who suffers from all the same real-life struggles Davidson has been open about: mental illness, substance abuse, grief over losing his firefighter dad on 9/11. Those aren’t exactly the same kind of issues that most of Apatow’s lazy-but-loveable goofballs who eventually get their lives in order have to deal with, and they’re certainly not the kind that’ll come to some happy resolution by the time the credits roll. And yet, despite that, at 137 minutes, The King of Staten Island could have easily been half an hour shorter. Davidson’s second attempt at turning a lens on his life, Bupkis, is far more satisfying. — BS
31. Year One (2009, producer)
Apatow performed an old-fashioned rescue op with his semi-newfound Hollywood clout: Get Harold Ramis back in the business of revue-style ensemble comedies. Jack Black and Michael Cera play cavemen wandering around the fringes of Biblical history; the curiosity cabinet of a cast also includes Oliver Platt, David Cross, Christopher Mintz-Plasse, Hank Azaria, Olivia Wilde, Bill Hader, Horatio Sanz and Vinnie Jones. The movie is a sloppy hit-and-miss affair, but maybe a little underrated; the shtickiness was so out of step with other 2009 comedies, and even moreso now, that it survives as an entertaining novelty act — and Ramis’s final film. — JH
30. Crashing (2017-2019, writer/director/producer)
When Crashing first premiered back in 2017, it earned some eyerolls for being yet another comedy about comedy, starring a stand-up comedian. But the semi-autobiographical Pete Holmes series had heart, and for all its self-importance, it delivered some memorable moments in its relatively short run. The scenes with Artie Lange, playing himself, are especially poignant. When the real-life Lange was arrested for cocaine and heroin possession during the show’s first season, Apatow reassured fans he’d still be in season 2, tweeting, “We would never give up on Artie or anyone struggling with addiction.” — BS
29. The Big Sick (2017, producer)
Whether with it’s Crashing or Trainwreck or The King of Staten Island or even, to an extent, Forgetting Sarah Marshall, Apatow has an obvious affinity for helping funny people in his orbit mine their real lives for inspiration. (Who can blame him? He’s good at it.) The Big Sick is no different, recounting the ways in which Kumail Nanjiani and his now-wife Emily Gordon navigated cultural differences and her rare, serious illness when they were first dating. It earned acclaim and a Best Original Screenplay nomination at the Academy Awards (we can’t give Apatow any credit for that — he left the writing to Nanjiani and Gordon). But in some ways, its protagonist is overshadowed by Ray Romano and Holly Hunter, who are both almost too good as Emily’s parents. — BS
28. Wanderlust (2012, producer)
Wanderlust isn’t the last Apatow Boom production about people of a certain age struggling with domesticity. It wasn’t even the last such project starring Paul Rudd in 2012; Apatow’s own This Is 40 came out later in the year. But this The State-adjacent comedy (David Wain directed it and co-wrote it with fellow State member Ken Marino) did establish, by flopping, sort of a post-Bridesmaids hangover for Apatow productions that were somewhat less predicated on dude-ly antics and tried harder than ever to give post-rom-com couples equal footing in the comedy. Wanderlust isn’t the strongest in that regard — Rudd gets a lot more laughs than Jennifer Aniston, who still tends to fall back into sitcom rhythms — but it’s also interesting to read as a struggle between making raunchy comedy and settling down into more sedate dramedy. In keeping with other Apatow productions, a more conservative approach to love and sex wins out. — JH
27. Get Him to the Greek (2010, producer)
No one’s watching a movie about bacchanalian rock-star excess starring Russell Brand and Sean Combs in 2024. (Wasn’t Jonah Hill even soft-canceled at some point?) There’s really no particular reason to check out this Forgetting Sarah Marshall spinoff focusing on Brand’s debauched space-case rock star and Jonah Hill as the aspiring record exec trying to control him. It was very funny at the time. There’s a surprisingly explicit threesome scene. Feel free to just take our word for all of this. — JH
26. This Is 40 (2012, writer/director/producer)
Paul Rudd and Leslie Mann weren’t necessarily the breakout characters from Knocked Up. If anything, they were the more familiar faces next to the fresh star turn for Seth Rogen. But their comically feuding couple, clearly at least somewhat inspired by Apatow’s own marriage to Mann, kept Apatow’s attention enough for a Rogen-free spinoff (and he’s threatened to make This Is 50 soon). It’s a pretty funny self-portrait, the flattery of self-casting as Paul Rudd mitigated by the truly rancorous family moments the movie depicts. The more limiting factor is how the movie is so ensconced in a particular upper-middle-class Los Angeles lifestyle. Still, it’s somewhat underrated. — JH
25. The Five-Year Engagement (2012, producer)
A more palatable (if less official) companion piece to Forgetting Sarah Marshall than actual spinoff Get Him to the Greek, here’s an Apatow production where characters circling thirty have problems with the way, not the will, to grow up. Life keeps obstructing the wedding plans of a youngish (but not-getting-any-younger couple) played by Jason Segel and Emily Blunt. There’s a refreshing lack of Hollywoodization to this pairing – Segel wants to be a chef, and Blunt is on a research professor track – and it’s all together less ramshackle (if also less memorable) than Sarah Marshall. – JH
24. The Ben Stiller Show (1992-1993, co-creator, writer and producer)
This well-liked Fox version of Ben Stiller’s comedy work at MTV only lasted a single season, a harbinger of what was to come for future Apatow series that would be even more beloved and even more missed when they were yanked off the air. This product of the early-’90s sketch-comedy boomlet goes heavy on the pop-culture riffs, making it both fascinating and a little peculiar as a time capsule of both the ‘90s and their own prismatic reflection of the ‘60s. (One sketch goes deep on an Oliver Stone amusement park featuring a Doors ride; a recurring bit has Bob Odenkirk playing Charles Manson in a variety of contexts.) In retrospect, this feels like Apatow as much as Stiller, and a sign both that he could play in a sketch-comedy sandbox even if perhaps his talents were ultimately better served elsewhere. — JH
23. Love (2016-2018; co-creator, writer and producer)
In The Return, Apatow makes a stand-up joke promoting this fellow Netflix production, noting that the show has been criticized on the same grounds as much of his other work, for pairing a beautiful woman with a sort of goofy-looking guy. He makes it the premise of a pretty good joke about how essentially, all women are kind of beautiful, and all men are kind of goofy-looking. Great, now explain how this is yet another margins-of-showbiz story, Judd! Admittedly, it’s a pretty good one, with misfit characters played by Paul Rust and Gillian Jacobs (with terrific support from Claudia O’Doherty and Mike Mitchell) struggling to accept themselves and each other. — JH
22. The Cable Guy (1996, producer and uncredited co-writer)
There must be a certain demented pride in being a major creative force behind Jim Carrey’s first post-superstardom flop, a dark media-warped comedy reconfigured from a more buddy-friendly script. Apatow didn’t receive credit for his extensive screenplay modifications, and while this wasn’t his final work with Carrey or Ben Stiller (who directed), it feels like a simultaneous peak and valley of his 1990s career: a big summer movie where he was denied writing credit, which then flopped anyway. Decades later, The Cable Guy is a fascinating artifact of Carrey’s comic contortions pushed into dark corners of the decade’s tabloid-influenced, dawn-of-convergence media landscape. — JH
21. You Don’t Mess With the Zohan (2008, co-writer)
A comedy about the conflict between Israel and Palestine is probably the last thing anyone wants to think about in 2024; it may not have even been especially in Apatow’s mind in 2008, as Sandler’s Happy Madison dusted off a script that Apatow worked on years earlier before 9/11 put the temporary kibosh on a comedy about an Israeli soldier (Sandler) who fakes his own death in the battle with a Palestinian fighter (John Turturro) and decamps for the United States to become a hairdresser. But as with Sandler, whose other characters tend to be more incidentally Jewish than really engaged with the idea of Jewishness, it’s a kick to see Apatow involved in something much more culturally specific (and just plain weird) than passing references. And at the time, believe it or not, You Don’t Mess with the Zohan — easily the silliest and funniest Happy Madison Sandler comedy of the 2000s — felt oddly nuanced in its depiction of its central conflict, including various terrorist acts, as essentially absurd. (To be honest, it feels more like Smigel than Apatow, but they both raise Sandler’s game.) Today, it’s a little harder to laugh at the image of an Israeli super-soldier, no matter how intentionally goofy — and it certainly doesn’t help matters that the movie’s two biggest Palestinian characters are not played by actors of Arab descent. The movie’s sunny capitalistic idealism, where people of all races and religions toil side by side in a New York City mall (?!), seems further away than ever for any number of reasons. But the sweetness of the movie’s ultimate message of melting-pot harmony still lingers. — JH
20. Forgetting Sarah Marshall (2008, producer)
If there’s an exact right age to experience an Apatow movie, I was it when Forgetting Sarah Marshall came out in 2008 — in college, with a photo of McLovin’s fake ID from Superbad taped to the outside of my dorm room door and some well-loved Freaks and Geeks DVDs that I lent out to at least three different people as my prized possession. I’m pretty sure I saw Jason Segel’s star-making turn as a guy who runs into his TV star ex-girlfriend on vacation in Hawaii in theaters on the day it came out, and I’m even more certain that I still know all the words to “Dracula’s Lament.” It may have hit me at the perfect moment, but sixteen years later, Forgetting Sarah Marshall holds up. Everyone remembers the male frontal nudity, which was somewhat groundbreaking at the time (and they should!), but ultimately it’s an incredibly sweet movie about getting comfortable enough with yourself to be an absolute weirdo and finding someone who embraces your quirks instead of trying to change you. — BS
19. Popstar: Never Stop Never Stopping (2016, producer)
This Lonely Island mockumentary featuring Andy Samberg as Conner4Real, a pop star who can only be described as “Macklemore if he got his start in the Beastie Boys, somehow,” bombed hard when it was released back in 2016. But it’s since become a cult classic — and rightfully so. The satire is spot-on, and the songs are funny (especially “Equal Rights,” a song in which Conner rails against homophobia while repeatedly insisting that he himself is not gay, before we cut to a confused Ringo Starr saying, “He’s writing this song for gay marriage like it’s not allowed. It’s allowed now”). The former Beatle is hardly the only big musician cameo in the movie, and the sheer number of celebs who answered the call to appear is probably a testament to how tightly written the movie is. Why it wasn’t immediately recognized as great, we’ll never know. Justice for the Style Boyz. — BS
18. Trainwreck (2015, director, producer)
Like Lena Dunham, Amy Schumer has a tendency to get in her own way sometimes, and she’s earned her fair share of backlash and ill will in recent years. But there’s no denying her performance in Trainwreck. And for as good as Schumer is as a hard-partying magazine writer tasked with profiling a more reserved sports doctor (Bill Hader), she’s also surrounded by an incredibly stacked supporting cast that includes Colin Quinn, Brie Larson, Vanessa Bayer, Tilda Swinton, Pete Davidson, Mike Birbiglia, John Cena in one of his first movie roles and of course, LeBron James playing a Downton Abbey-loving version of himself. Funny yet touching, with a massive cast of supporting characters ready to steal scenes at any moment, it’s everything we’ve come to expect from an Apatow movie. — BS
17. Anchorman 2: The Legend Continues (2013, producer)
Part legacy sequel, part culmination of nearly a decade’s worth of comedy successes and part season (or series?) finale on the Will Ferrell/Adam McKay partnership, Apatow returned to the Ferrell fold for a mega-movie reunion of the Channel 4 news team, almost 10 years after the first movie became a semi-surprise hit. Was Apatow’s imprint even particularly necessary on a project that was already wrangling Ferrell, McKay, Steve Carell, Paul Rudd, David Koechner, Kristen Wiig, ‘80s period detail, a satire of cable news, hours of improvisation and a dozen or so ultra-high-profile celebrity cameos? (Maybe his Rolodex came in handy on the last one.) That muchness indicates why Anchorman 2 can’t operate with quite the same quick-footed dexterity as its predecessor, but as a mega-comedy fever dream that inadvertently sent off the whole McKay/Ferrell partnership (still the best work either of them have done), it’s become weirdly underrated. — JH
16. Knocked Up (2007, writer/director/producer)
For better or for worse, Knocked Up is probably what most people think of when they think of “a Judd Apatow movie.” It’s got an underachieving man-child paired up with an out-of-his-league woman and surrounded by a strong supporting cast of frequent collaborators, and it tracks the evolution of said man-child as he learns to embrace domesticity. Katherine Heigl famously distanced herself from the movie after it was released, claiming it was “a little sexist” and that it “paints the women as shrews.” Apatow and Seth Rogen both got a little defensive in their response, but the former did hit the nail on the head when he explained that the characters are indeed sexist at times because “it’s really about immature people who are afraid of women and relationships and learn to grow up.” In other words, it’s not an endorsement of their behavior; we’re supposed to laugh at them, not with them, and with that in mind, there are plenty of laughs to be had. — BS
15. Comic Docs: The Zen Diaries of Garry Shandling; George Carlin’s American Dream; Bob and Don: A Love Story
There is arguably no one more enamored with the art of comedy than Judd Apatow. In addition to all of his own contributions to the genre, he’s written and/or edited three books about the craft. (We’ve excluded those from this list to focus purely on Apatow’s onscreen endeavors.) The documentaries that he’s made about some of his comedy heroes — George Carlin, Bob Newhart, Don Rickles and his mentor Garry Shandling — are all loving tributes that are expertly assembled by a real student of the art form who wants to preserve their legacy. The Zen Diaries of Garry Shandling, put together shortly after Shandling’s unexpected death by pulmonary embolism in 2016, is the most moving of the bunch. Given how close he was to Shandling, Apatow is able to assemble a real treasure trove of old diary entries, letters, photographs and old footage and put together a portrait that feels as much like a eulogy for the man and his approach to life as it is a document of his comedy prowess. — BS
14. Walk Hard: The Dewey Cox Story (2007, writer and producer)
It’s wild to think that in the same year that Superbad and Knocked Up were released, Apatow also managed to put out the best musical parody since This Is Spinal Tap. While Spinal Tap spoofs rock docs, Walk Hard sets its sights on musical biopics, particularly the kind of formulaic Oscar bait like Ray and Walk the Line that dominated awards shows just a few years before its release. Those two movies are the obvious targets here, with much of Dewey Cox’s life and career spoofing those of Ray Charles and Johnny Cash, but Dewey is essentially the Forrest Gump of the music industry, stumbling his way through his own Bob Dylan era and experimenting with psychedelia after meeting the Beatles (played, memorably, by Jack Black, Justin Long, Paul Rudd and Jason Schwartzman). The humor is absurd at times, as when young Dewey sings the blues after accidentally cutting his brother in half with a machete, but the details — like a running gag where he repeatedly rips sinks from walls, as Joaquin Phoenix does in one memorable scene from Walk the Line — are spot-on. — BS
13. Bridesmaids (2011, producer)
One of the early criticisms of Apatow’s work was that it was too male-centric, that the women in his films weren’t fully fleshed out, instead existing mostly to react to the men. But he righted that ship when he reunited with Paul Feig for Bridesmaids, a comedy centered around an ensemble of women. The Kristen Wiig movie proved to anyone who wasn’t already aware that women can be just as raunchy and gross as men, and they can be funny as hell doing it. The response was overwhelming; Bridesmaids raked in a whopping $306 million worldwide, overtaking Knocked Up as the highest-grossing Apatow movie, and it even earned Melissa McCarthy — who steals every scene she’s in — a Best Supporting Actress nomination at the famously comedy-averse Academy Awards, making it the first Apatow movie to be nominated for an Oscar. — BS
12. Undeclared (2001-2002, creator/writer/producer)
When Freaks and Geeks was canceled in the spring of 2001, Apatow led a few of its actors through an accelerated graduation and matriculation into the college-set sitcom Undeclared. Most notably, Seth Rogen made the leap from one supporting part to another, and got a writing-staff job to boot. The Undeclared writing staff didn’t actually have much overlap with Freaks and Geeks; that show’s co-creator Paul Feig directed one episode but wasn’t a staffer. Without Feig, or the hourlong dramedy format that allowed Geeks a little more range, it’s arguably the more Apatovian production of the two — more comedy-forward and bro-ish. Within those parameters, though, this is a terrifically funny and underseen show that’s actually about 19-year-olds acting more or less their age, rather than 29-year-olds acting a decade or more younger. It feels weirdly influential on New Girl, of all things, for the character quirks gradually revealed (and, most likely, developed) over the course of an extended hangout. — JH
11. Pineapple Express (2008, co-writer and producer)
Is David Gordon Green the best director Judd Apatow has ever worked with? Greg Mottola, who helmed Superbad and a bunch of Undeclared episodes, and Lena Dunham both provide some decent competition, but most of Apatow’s stable tends be writers-turned-directors doing their best to honor the performing styles of the comedians at the center of the enterprise. Green, though, brings a very particular visual sensibility to his work, even (or maybe especially?) when that work is an ‘80s buddy-comedy/stoner adventure pastiche cooked up by Seth Rogen and Evan Goldberg. At the time, Pineapple Express seemed like a major departure from Green’s indie sensibilities, but he’s since shown himself to be the kind of quasi-journeyman who can express his quirky, post-industrial humanism across a variety of genres. — JH
10. Funny People (2009, writer/director/producer)
It’s not meant as a dig that only two of Apatow’s features as a writer/director make it into the top 10 of his various projects. It was meant as a dig, however, when critics and audiences in 2009 discussed the film’s 146-minute running time, perhaps the apex of the Apatow Runtime Complaint, namely that he makes comedies that match the lengths of Oscar dramas or superhero epics. Apatow has memorably and understandably responded to this, pointing out how avid binge-watchers will consume three or four hours of TV in a single sitting, but he still gets dinged. But the unusual runtime and structure is exactly what makes Funny People, a dramedy about a lonely and mercurial superstar (Adam Sandler) mentoring a desperate younger comic (Seth Rogen), so piercing, interesting, and, yes, unwieldy. — JH
9. The Critic (1994-1995, writer/producer)
His spec script might have waited until he hit it bigger, but Apatow did get his animated-sitcom shot with this short-lived Simpsons companion piece from producers Al Jean and Mike Reiss, following the misadventures of New York City film critic Jay Sherman (voiced by Jon Lovitz in his best role). Jay’s position on the outskirts of Hollywood, a career defined by it but not a part of it, makes for a less directly aspirational show than some other Apatow-related stories of industry strivers (even if Jay’s lifestyle, whatever its cartoon indignities, does seem pretty enviable, not least because he’s paid a full salary to review movies). The Critic signaled the more outlandish direction The Simpsons was moving towards in what turns out to still be its relatively early years, and as far as pure gag writing, it may represent a kind of peak for Apatow — though as always with staffers whose names aren’t on dozens of episodes, it’s difficult to parse his exact input. Then again, I recently rewatched the one episode where he has the sole writing credit, a seemingly stock Jay-runs-a-marathon-to-prove-himself story called “Marathon Mensch,” and it would probably qualify as the funniest half-hour of the month if it were released today. — JH
8. The 40-Year-Old Virgin (2005, writer/director/producer)
In lesser hands, Judd Apatow’s directorial debut, co-written with star Steve Carell, would be too gross or too creepy. But The 40-Year-Old Virgin, about, as you might guess, a man in his 40s who has never had sex, is deceptively sweet. There’s nothing fundamentally wrong with Andy (Carell) other than a lack of confidence, and his friends and coworkers’ misguided attempts to help him lose his virginity are, at their core, rooted in a desire to help him get more comfortable with himself and find happiness. And of course, for a movie whose whole premise centers around trying to get a man laid, there is virtually no sex, save for the big finale when Andy and his love interest Trish (Catherine Keener) finally do the deed after getting married and Carell leads an elaborate performance of “Aquarius/Let the Sunshine In.” It’s a perfect balance of raunch and romance, and in many ways it’s a heartwarming coming-of-age tale about a guy who just happened to come of age at age 40. — BS
7. Talladega Nights: The Ballad of Ricky Bobby (2006, producer)
Hot off of the success of Anchorman, Adam McKay and Will Ferrell famously sold Talladega Nights with a six-word pitch: “Will Ferrell as a NASCAR driver.” That’s pretty much all you need to know about this one too. Talladega Nights sees Ferrell firing on all cylinders and relies heavily on his easy chemistry with John C. Reilly — a dynamic that would later result in the brilliant Step Brothers — and a delightfully villainous performance by Sacha Baron Cohen. Is it the funniest movie any of these guys have made? No, but that’s not to say it’s not still damn funny. If anything, it’s evidence that when you’re able to get the right people in a room together the way Apatow has famously done throughout his career, sometimes all you need is a six-word premise. — BS
6. The Larry Sanders Show (1992-1998, writer/producer)
Like The Critic, this is a showbiz satire that Apatow didn’t originate, serving as a producer and writer (and directing one episode in the show’s final season) for someone else’s broader vision. Unlike The Critic, this one’s broader vision resonated beyond a cultish subsection of Simpsons fans. Star Garry Shandling, who opted to create a fictional late-night talk show host rather than enter himself into the Late Night Wars fray of the early ‘90s, became a mentor for Apatow, and though Apatow’s own work would veer less acerbic and satirical than this wonderfully tart showbiz drollery, you can see in Larry Sanders how he might have learned to tease a more human sensibility from his comedy-nerd joke-writing. — JH
5. Step Brothers (2008, producer)
Summer 2008 wasn’t that far into Judd Apatow’s Hollywood dominance. It was only three years out from 40-Year-Old Virgin, a year after Knocked Up and mere months after Forgetting Sarah Marshall. Yet — perhaps due to their familiarity with these various man-children characters — Adam McKay and Will Ferrell were already making a stealth satire of the coming-of-age comedy predicate on grown men getting their shit together. Hence Step Brothers, which comes on like the usual outlandish antics awaiting growth, until it becomes hilariously and dismayingly clear that the reluctant fortysomething best friends played by Will Ferrell and John C. Reilly are, in fact, closer to the sensibilities of aggrieved 10-year-olds — aggressive, emotional, terrified of women — than the perpetual decade-behind adolescence depicted in something like Knocked Up. In an even finer twist, McKay, Ferrell and Reilly then depict the usual Apatow redemption arc as a deadening hell of corporate banality — in other words, what’s really more likely to await when you finally do get your shit together. The movie is also, incidentally, screamingly funny, its small suburban scale allowing Ferrell and Reilly to produce perhaps the greatest, nuttiest product of Apatow’s improv-friendly style. Like his expanded running times, that technique has gotten blamed for every clumsy attempt to replicate it in lesser hands. But with the right discipline, it’s a bold gambit that pays off with a comedy classic. — JH
4. Girls (2012-2017, writer/producer)
By the early 2010s, just about every dude in Apatow’s orbit had been given a chance to star in and/or write their own comic vehicle, and while maybe it shouldn’t have taken that long for him to turn his eye toward similarly funny and unconventional women, it’s hard to argue against the dividends — unless you, like a vocal faction of people, absolutely loathe Girls, Lena Dunham’s millennial Sex and the City riff that aired for six seasons on HBO. Frankly, at the dawn of an era where so much “prestige” TV got an instant critical pass, it’s bracing to watch a show that actually, actively repulsed some people, with a potent mix of cringe comedy, character study and the kind of short-story sensibility that fueled Mad Men (with which Girls has way more in common than you might think). Something else that may get lost among Dunham’s real-life antics, Adam Driver’s quest to work with every great director in Hollywood and the anti-zen of Marnie Michaels is the fact that this is one of the most Apatow-heavy TV shows on his filmography. All told, he co-wrote 10 of the show’s 62 episodes, including the instant classic “Beach House.” Dunham’s voice is all over the show (not to be outdone, she has a writing credit on about two-thirds of the episodes, which is astonishing in retrospect) but given her lack of TV experience at the time Girls was greenlit, it’s safe to say Apatow and producer Jenni Konner were instrumental in turning Dunham’s vision into one of the best TV shows of the 2010s. — JH
3. Anchorman: The Legend of Ron Burgundy (2004, producer)
It’s the movie that inspired this list, and it’ll stand the test of time as one of the most quotable comedies of all time. Millennials of a certain age can, in fact, communicate almost exclusively in Anchorman quotes, whether they’re rattling off old chestnuts like “60 percent of the time, it works every time,” “I love lamp” or “It’s so damn hot, milk was a bad choice” or spitting out deeper cuts like “The human torch was denied a bank loan” and “I have many leatherbound books, and my apartment smells of rich mahogany.” It’s undeniable what mark the saga of a sexist 1970s San Diego news anchor and his new female partner left on pop culture. Will we ever see a broad, silly comedy have a similar impact again? It feels unlikely. They don’t make ‘em like they used to. — BS
2. Superbad (2007, producer)
As mentioned earlier, Garry Shandling served as a mentor for Apatow in the early years of his career, and he clearly sought to pay this relationship forward, helping several of his Freaks and Geeks stars realize their film careers. In the case of Seth Rogen and his bestie Evan Goldberg, they would go on to become nearly as prolific comedy producers as Apatow himself, which makes Superbad seem like an epic crossover in retrospect. In reality, it was the undercard comedy event of summer ‘07, with the Rogen-starring Knocked Up gathering more early buzz for its high-concept bro-friendly logline: What if a one-night-stand pregnancy between two polar opposite people was carried to term? Superbad, meanwhile, sounds almost generic: a couple of best friends (get this: one is a fast-talking loudmouth and the other is more cautious and openly neurotic!) want to party. But Apatow helped guide Rogen and Goldberg — who had been working on this screenplay since they were younger than their teenage avatars, played by Jonah Hill and Michael Cera, respectively — toward an all-timer in the genre of “guys want to party.” Specifically, high school seniors Seth (Hill) and Evan (Cera) are on a mission to procure alcohol for a party where they hope to impress (and possibly inebriate) their respective crushes. (Seth’s is a debuting Emma Stone!) Yes, yes, problematic stuff — but honestly, even though it was made nearly 20 years ago and its creators have said that certain moments wouldn’t fly now, Superbad manages to be both true to its characters and clearheaded about the foolishness of their plan, with multiple main characters voicing their objections. Of course, consummating these relationships isn’t exactly the point anyway; this is a love story between two teenagers who have only belatedly begun to imagine a life outside their lifelong friendship. All of the raunchy dialogue and dudes-on-a-mission silliness builds to an utterly lovely series of parting shots. Rogen and Goldberg have made plenty of good movies since, but the unique emotional center of Superbad suggests that maybe Apatow had a hand in its particular, near-perfect tone. For all the durability of watching adult men and women grapple with themselves and their responsibilities, it turns out an actual, straightforward coming-of-age story (and the truest successor to the show taking the No. 1 spot on this list) is even better. — JH
1. Freaks and Geeks (1999-2000, writer and producer)
As should be clear by now, Apatow’s greatest gift is his skill as a collaborator who knows how to bring out the best in a variety of comic talents. His career has seen no greater collaboration than his work with Paul Feig, a near-perfect 18-episode series that languished in ratings hell for most of its run (to the extent that it was allowed to run at all; its final three episodes were burned off on a single Saturday the summer after its only season, and one episode never aired in the U.S. until it entered cable reruns). Some of its genius is right there in the title: By focusing on a trio of teenage geeks and a group of burnout “freaks” befriended by ex-geek Lindsay Weir (Linda Cardellini), the show had the space to indulge fractious, stoner-adjacent screw-ups as well as heartfelt and hilarious chronicles of adolescent nerdery. Despite the male-heavy cast, it boasts a better gender balance than a lot of Apatow’s future projects, with Cardellini’s note-perfect performance at the center. It was a kick to see Apatow and Feig later find much-deserved success as filmmakers (who still found time to dip into TV, stand-up and the occasional book), but Freaks and Geeks has an old-school collective craft that’s irresistible and all the more valuable in retrospect: It is thoroughly and unapologetically an episodic network TV series, and the craft of its writing, acting and directing rivals classics of the form like Seinfeld. Even after plenty of obsessive rewatches, the show has a true sense of discovery from its young cast, who never look as well-scrubbed and magazine-ready as so many of their counterparts from this era of teen shows — it’s probably a big part of why the show didn’t catch on, Dawson’s Creek-style. With one 18-episode series, Apatow helped launch a dozen great careers and inspired as many young viewers as his idols did. If it seems unlikely he’ll ever top it, well, look, how often does anyone get to come of age a second time? — JH
