From Year One to this week’s The King of Staten Island.

Photo-Illustration: Vulture

This article has been updated to include Apatow’s recent films, including this week’s The King of Staten Island.

The Judd Apatow Cinematic Universe is more than the work of just one man. And yet, whether Apatow writes, produces, or directs a film, his bighearted sensibility permeates the final product: that giddy, mockingly irreverent attitude toward romance and family that, nonetheless, has a deeply sentimental core.

It’s been more than a decade since Apatow moved from TV (he was a writer-producer for the likes of The Larry Sanders Show, The Ben Stiller Show, and Freaks & Geeks) to become one of Hollywood’s most bankable, distinctive comic filmmakers with The 40-Year-Old Virgin. But even before that, his affectionate, bro-friendly aesthetic — which had been honed from years of stand-up and writing jokes for comics such as Roseanne — could be felt in projects he wrote and produced, like The Cable Guy and Celtic Pride. But after Virgin, Apatow films were everywhere.Teaming with stars like Adam Sandler and Will Ferrell, he established a reputation for making smart variations of the typical mainstream broad comedy that celebrated overgrown adolescents but secretly hoped they’d one day find a good girl and settle down. Over time, Apatow’s approach has matured and grown more sophisticated, but that core pleasure remains.

To celebrate Apatow’s growing oeuvre, we’re ranking the best of his movies. But first, some ground rules. Because we’ve already chronicled the highs and lows of Ferrell’s career, we’re leaving off the movies they made together: Anchorman, Anchorman 2, Step Brothers, Talladega Nights, and Kicking & Screaming. And we’re also skipping Begin Again, the Keira Knightley–Mark Ruffalo musical drama that Apatow produced — because, frankly, it’s so thematically and tonally removed from the Judd Apatow Cinematic Universe we’re not entirely convinced IMDb isn’t actually screwing with us.

25. Year One (2009, producer)
What must have sounded like a good idea in the pitch — Jack Black and Michael Cera as sort of proto-cavemen — is an absolute disaster onscreen. Black looks so bored and Cera looks so deeply uncomfortable and displeased to be there that it’s little wonder both actors essentially rebooted their entire careers after this tanked in theaters. This is the nadir of the Apatow universe, a film that comes dangerously close to being a vicious accidental satire of Apatow’s entire comedic vision: dumb stoners roaming around an ugly set saying non sequiturs for quick cash. Want to know the worst part? This was Harold Ramis’s last film.

24. Heavyweights (1995, writer, executive producer)
Apatow has said that Heavyweights was born from the idea of “a prison-break movie set at fat camp,” and the thing about that idea is, well, it’s really not all that funny. The movie gives the kids (including a young Kenan Thompson) a certain dignity, which is to be admired, we suppose, but this is still nothing but fat jokes and a frighteningly hammy performance from Ben Stiller as a self-help guru who is using the camp to try to make a line of workout videos. (One gets the sense that if Stiller could buy up all the DVDs of this one, he would.) None of the kid actors are particularly distinguished and, honestly, this movie seems beamed in from another planet entirely. Of note for Apatow completists: Paul Feig, director of Bridesmaids, has a leading role as a skinny camp counselor. He doesn’t look particularly comfortable.

23. Celtic Pride (1996, writer, executive producer)
Again, a good idea: Two white Boston fans (Dan Aykroyd and Daniel Stern — a odd pairing, to be sure), afraid they’re going to lose to Utah in the NBA Finals, kidnap the Jazz’s star player (Damon Wayans) before Game 7. Lots could be done with this concept — the inherent irrationality of sports fandom is begging to be satirized — but the film doesn’t capitalize on any of it. Instead, you get a lot of mugging and screaming from the two leads and no real evidence that Apatow was even near the set during filming. Celtic Pride came out a month before The Cable Guy, delivering a one-two punch to Apatow’s movie dreams and sending him back to TV. For a while.

22. Drillbit Taylor (2008, producer)
At the time of its release, Drillbit Taylor had a cloud hanging over it: This Apatow-produced teen comedy was one of Owen Wilson’s first films after recovering from his 2007 suicide attempt. That timing didn’t do this lackadaisical film any favors. Playing a liar and panhandler who becomes a bodyguard for some high-school geeks, Wilson is his usual charming and loopy self, but Drillbit Taylor (co-written by Seth Rogen) is an infinitely lamer version of Superbad’s combo of boisterous adolescent laughs and unexpected sweetness. Apatow’s wife, Leslie Mann (a constant bright spot in his films), has some flirty fun as Wilson’s love interest, but everybody involved with this dud has been much, much better somewhere else.

21. Fun With Dick and Jane (2005, writer)
Such a waste of an opportunity that it’s still frustrating a decade later. This remake of the 1977 comedy follows an upper-middle-class couple (Jim Carrey and Téa Leoni) as they resort to crime after the company they work for turns out to be an Enron-level disaster. This is fertile territory, particularly at this specific time in American history, but the movie has little to no interest in following up on any of it. It’s far more comfortable just ceding the whole screen to Carrey, who is capable of playing real characters but does the exact opposite here, hamming and mugging away in one of his absolute worst performances.

20. Get Him to the Greek (2010, producer)
Sure, Russell Brand’s obnoxious British rock-star Aldous Snow was a kick in Forgetting Sarah Marshall, but did we really need a whole movie about him? Universal thought so, so we got this tiresome comedy about an uptight music executive (Jonah Hill) who has to ensure that the volcanic Snow makes it to a crucial comeback gig. Get Him to the Greek is far more interesting as a time-capsule memento: It documents that short, strange period when Hollywood thought Brand was going to be huge, Hill’s bread and butter was playing shlubby dorks in broad comedies, and dramatic actress Rose Byrne (who’s hilarious as Snow’s pop-star girlfriend) hadn’t yet figured out that she was one of her generation’s greatest comedic dynamos.

19. Juliet, Naked (2018, producer)
Apatow has worked on a lot of films about immature men, but director Jesse Peretz’s adaptation of a Nick Hornby novel shows what happens when the execution falls flat. Chris O’Dowd plays Duncan, a superfan of a faded fringe singer-songwriter (Ethan Hawke). Duncan’s longtime girlfriend, Annie (Rose Byrne), has never understood the appeal, but when she begins an unexpected email correspondence with the artist, she starts to see him — and her relationship with going-nowhere Duncan — in a new light. Juliet, Naked is a quirky romantic comedy helped immensely by its three appealing leads. But it’s also fatally adorable in how it depicts these mismatched characters and their ho-hum problems. As a result, this tame date movie isn’t nearly as anarchic or wise as Apatow’s best man-child manifestos.

18. This Is 40 (2012, writer, producer, director)
Yeesh. A movie so navel-gazing — not only does Apatow cast his own wife and kids as his wife and kids, and Paul Rudd as a charming record-exec-dude version of Judd Apatow, he also spends half the film trying to get us to buy Graham Parker albums — that watching it feels like being stuck at a neighbor’s house while he shows you pictures of his family’s vacation to suburban Los Angeles. The Wealthy, White Ennui is oppressive throughout, but the worst part is that the movie isn’t even funny. This is Apatow out of ideas and just grabbing at everything in arm’s reach; this is Apatow as that date who never asks you any questions about your life. And it’s nearly two-and-a-half hours long!

17. You Don’t Mess With the Zohan (2008, writer)
Those who complain that Adam Sandler just serves up lazy mainstream comedies tend to forget this commendably nervy satire about an Israeli commando (Sandler) who runs off to New York to follow his bliss and become a hairdresser. Co-written by Apatow, alongside Sandler and Robert Smigel, You Don’t Mess With the Zohan is a grenade hurled clumsily at politically correct watchdogs, mocking both sides of the Israeli-Palestinian conflict when it’s not making obvious jokes about randy middle-aged women or giddily spoofing action-movie tropes. But “commendable” only gets you so far, and Zohan’s hit-to-miss joke ratio is, well, about as good as any of Sandler’s lazy mainstream comedies. That said, we’d support any Kickstarter effort to finance a spinoff film focusing on John Turturro’s nutso terrorist character.

16. Wanderlust (2012, producer)
One of those cases where a lot of funny people get together and the sparks just don’t fly, Wanderlust unites director–co-writer David Wain with Paul Rudd and Jennifer Aniston as upwardly mobile New Yorkers who move to a Georgia commune in order to change their lives. A top-notch supporting cast that includes Ken Marino, Keegan-Michael Key, Jordan Peele, Malin Akerman, Kathryn Hahn, and Alan Alda does little to help this genial but forgettable “hippies sure are goofy” comedy. Justin Theroux is really funny as a condescending tree-hugger, but in retrospect, it might have been better if the filmmakers had just scrapped the whole plot and let Rudd’s character try to talk dirty for 90 minutes.

15. May It Last (2017, director, producer)
Apatow’s lone feature documentary — co-directed with Michael Bonfiglio — follows the Avett Brothers during the making of their True Sadness album. (It played in theaters for one night before airing on HBO.) If you love the Avett Brothers, you’ll love this movie; May It Last is made with a gentle fan’s touch, and you get a real sense of how the brothers’ affection for each other and their family history infuses their music. But if you don’t know the band, you’ll be on the outside looking in. Apatow loves the Avett Brothers, and why not? They’re a great band. But that’s mostly all the movie has to say. Still, we’re glad Apatow seemed to enjoy himself so much making it.

14. The Five-Year Engagement (2012, producer)
Inevitably, as Apatow and his Rogen-Segel-Franco crew aged, their movies leaned toward themes of growing older and having a life with stakes and consequences. The problem here is that this film is about the dissolution of a relationship but it never quite steps outside of that sad-sack “Why won’t she love me?” Apatowianism. Segel (who co-wrote this film) loves his girlfriend (Emily Blunt, mostly wasted), but they can never quite get it together, and after the umpteenth scene of them fighting with each other, you find yourself cheering for them to break it off already. This is only pretending to be a mature comedy. The movie also doesn’t even realize that its supporting characters should be the leads; no offense to Segel or Blunt, but when Chris Pratt and Alison Brie (with a British accent!) have this much chemistry together, you just give the movie over to them.

13. The Cable Guy (1996, producer)
A critical and commercial disaster at the time, The Cable Guy has developed an admiring cult over the years — especially among those who appreciate how Jim Carrey (the world’s biggest comedy star of the time) conspired with director Ben Stiller to make an unapologetically dark character piece far removed from Ace Ventura. More daring than it is successful, the film gets a lot of mileage out of the odd-couple tension between Carrey’s psychotic cable guy and Matthew Broderick’s milquetoast dweeb. The Cable Guy isn’t always funny but it’s always uncomfortably strange, as Carrey tries to seduce his hesitant new buddy into becoming closer and closer friends. (Apatow, who served as producer, worked on the script but didn’t receive credit.) One suspects that in our Adult Swim modern era, The Cable Guy would have found its audience easier, but back in 1996, it was simply too prickly for its own good.

12. Forgetting Sarah Marshall (2008, producer)
Here Segel works much better (in another film he wrote), as a hopelessly brokenhearted TV producer who goes all the way to Hawaii to escape his TV-star ex-girlfriend (Kristen Bell), only to see her show up there with her new rock-star boyfriend (Russell Brand, who has never been better in a film since). Here the woeful sad-sack character that’s a staple of Apatow films works, partly because Segel plays him so winsomely, and mostly because he’s written so sincerely. Not everything about the Mila Kunis character works — she’s a little too Perfect Woman for Sad Sacks — but the Dracula puppet-show ending remains perfect.

11. Popstar: Never Stop Never Stopping (2016, producer)
All right, so it runs out of steam as it goes along, the songs (outside of “Finest Girl (Bin Laden Song)” and “Equal Rights”) aren’t top-shelf Lonely Island, and the celebrity cameos provide diminishing returns each time a new one shows up. It’s still funny — almost an updated, less movie-obsessed “Walk Hard,” with Andy Samberg and company satirizing musical genres one suspects Apatow doesn’t listen to a lot of. One thing the Lonely Island guys and Apatow have in common (other than penis insecurity): They’re all good-hearted, gentle satirists, so while the laughs come at you fast, they’re delivered with far more sweetness than bile. This is all good fun. And it is a LOT of good fun.

10. Funny People (2009, writer, director, producer)
Yes, Funny People is Apatow’s longest film as a director — the overstuffed two-and-a-half-hour epic he had the clout to make only after Knocked Up’s box-office triumph. And sure, it meanders badly, not just telling the story of an aspiring comic (Seth Rogen), but also a lazy movie star (Adam Sandler), his ex (Leslie Mann), and her husband (Eric Bana). Nonetheless, this is a laudable swing for the fences, with Apatow trying to become the new James L. Brooks by merging comedy, romance, drama, and slice-of-life wistfulness into an often-perceptive look at the business of being funny. Outside of Punch-Drunk Love, Sandler has never been better or more revealing, dissecting his lowest-common-denominator appeal with a blunt honesty he rarely allows. Indulgent and undisciplined as Funny People may be, it’s also kinda thrilling, with Apatow taking risks and encouraging his star to do the same.

9. Walk Hard: The Dewey Cox Story (2007, writer, producer)
An intriguing and essential entry in the Apatow canon because it, unlike so much of his other work, never once attempts to be “serious” or emotional. This is just a flat-out spoof, and it’s a terrific one. John C. Reilly plays the eponymous Dewey Cox, a country singer who breaks big and becomes a perfect clothesline for an impressive series of gags about music biopics, particularly Ray, Walk the Line, and even The Doors. This is as close to an old Zucker brothers’ joke-fest as you’re going to find anymore, and though not all the gags score, most of them do. And every scene with Tim Meadows trying to stop Dewey Cox from doing drugs is perfect. This is a dark fucking period!

8. Trainwreck (2015, director, producer)
Here’s where Apatow confidently enters his veteran-comedic-filmmaker period, smoothly directing Amy Schumer’s script about a commitment-phobic men’s-magazine writer (Schumer) who falls for a good guy (a superb Bill Hader). Trainwreck is the sort of New York–set comedy-drama that once made Woody Allen a legend, capturing the city as an endlessly romantic, bustling place where interesting, flawed people stumble over each other on the path to love. (Tellingly, Schumer takes a shot at Manhattan and Soon-Yi.) LeBron James is hilarious playing himself, Colin Quinn might actually make you teary-eyed, and a who’s who of reliable comedic supporting players — everyone from Vanessa Bayer to Randall Park to Jon Glaser — are a constant delight. This is one of Apatow’s most polished and mature film, which doesn’t mean there isn’t room for good oral-sex jokes.

7. The King of Staten Island (2020, director, producer) 
For all the focus on yet another immature lead character who tries to learn how to grow up and join life with the rest of us, The King of Staten Island really does show a legitimate evolution for Apatow, and a desire to grow. Ironically, that’s because his focus this time is on a kid named Scott (Pete Davidson, who co-wrote based on his own life story) who isn’t just in a state of arrested development; he’s truly, profoundly damaged. That tension, between Davidson’s pain and stubborn resistance to change and Apatow’s traditional coming-of-age, gives The King of Staten Island some real dramatic friction, making it a compelling watch even when Apatow, as usual, wanders off course occasionally. (He wouldn’t be our first pick to direct an attempted robbery that’s meant to be taken even slightly seriously.)

Davidson is the center of the film, but the real heart is found in the people who surround him and try to both help him and keep themselves sane in forever-shifting orbit: Marisa Tomei is wonderful as Scott’s mother; Steve Buscemi hits home as the fire chief who knew his late father; Bel Powley elevates a rote role as the pseudo-love interest who cares about him but doesn’t want to be dragged down by him; and best of all, Bill Burr is oddly searing and real as the potential stepfather who wants to help this kid but has plenty of his own problems. Yes, the movie is too long and has too many unnecessary subplots. But it steers toward truth and honesty in a way Apatow’s movies haven’t always. Moving forward, this is a very good sign for Apatow.

6. The Big Sick (2017, producer)
The story goes that Kumail Nanjiani met with Apatow to pitch an idea about a ghost witch. Only when that went nowhere did Nanjiani decide to tell the producer about something more personal, the story of how he and his wife (screenwriter Emily V. Gordon) met. Thank God for second chances, both in pitch meetings and in relationships. The Big Sick is the result of that pitch, as Nanjiani and Gordon scripted their initial courtship, unfortunate breakup, and her subsequent stay in a hospital after she fell into a coma. One of 2017’s best feel-good comedies, The Big Sick earned the screenwriting duo an Oscar nomination and helped launch Nanjiani to a whole new level of stardom. But the whole ensemble shines, particularly Holly Hunter and Ray Romano as Emily’s beleaguered parents facing their own relationship issues.

5. Pineapple Express (2008, producer)
This was the brief moment when it seemed that the Apatow stoner aesthetic, adapted by an indie filmmaker who had a way of wordlessly elevating every scene, could produce something approaching art. Pineapple Express is funny, to be sure, but it also raises the stakes, putting our two heroes (Seth Rogen and James Franco, in what we personally think might be the best non–Spring Breakers performance he’ll ever give) in a murder plot that actually requires them to engage, at last, with the world around them. The ending is a little too self-consciously “We’re doing ’80s-movies tropes!” and seeing where David Gordon Green would go after this slightly devalues what he was going for here, but this is as daring and original a movie about the friendship between dealer and stoner as humans could possibly conceive.

4. Superbad (2007, producer)
2007 was the Summer of Judd, thanks to the smash success of Knocked Up and this Apatow-produced high-school comedy about two dorks (Jonah Hill and Michael Cera) looking to get laid before they graduate. Superbad was written by Seth Rogen and his partner Evan Goldberg, and alongside director Greg Mottola, they captured the horny, anxious flop-sweat of life as a teenage boy: Your hormones make you feel invincible, but your hopeless awkwardness remind you what a putz you really are. Like a lot of high-school movies, Superbad is really about the pain of saying good-bye to childhood, but it’s consistently raucous enough that the sneaky sentiment surprises you. And it’s a sure bet that, eight years later, a lot of people still think Christopher Mintz-Plasse’s real name is McLovin.

3. Knocked Up (2007, writer, director, producer)
Knocked Up signaled the moment when critics started taking Apatow seriously as a comedy auteur, which has been a mixed blessing considering the sometimes self-indulgent tone his movies have taken since. Nonetheless, Apatow’s second feature has a killer hook: Prototypical slob (Seth Rogen) has drunken one-night stand with a classic uptight workaholic (Katherine Heigl), getting her pregnant in the process. The setup plays out predictably — the immature man-child grows up — but Apatow’s screenplay is full of texture and heartfelt observations: how nobody ever really feels like an adult, how life is what happens when you’re busy making other plans, whether Steely Dan are incredible or gargle balls. Watch Knocked Up now, and there’s an extra layer of poignancy: Heigl bad-mouthed the movie after its release and yet never got close to making anything as good again.

2. The 40-Year-Old Virgin (2005, writer, director, producer)
The movie that finally broke Apatow and ushered in a whole decade of comedy is still the funniest, sweetest, and most original of all of Apatow’s personal productions. Sure, this has all the regular gags — and ten years later, even when it could be considered “problematic,” the “You know how I know you’re gay?” battle between Paul Rudd and Seth Rogen seems to sum up every white heterosexual teenager we’ve ever met — and the Apatow signature of overgrown man-children putting off adulthood. But it also has a huge-hearted, star-making performance from Steve Carell at its center, a legitimately complicated romantic lead (played by Catherine Keener!), and as deep a comedy bench, right before they all exploded, as you will find. Seriously: Rudd, Rogen, Elizabeth Banks, Romany Malco, Jane Lynch, Mindy Kaling, Kevin Hart, Kat Dennings, and Jonah Hill as a reasonably befuddled customer.

1. Bridesmaids (2011, producer)
Apatow’s best film brought him full circle, reuniting him with Freaks & Geeks partner Paul Feig to produce a very funny comedy co-written by Saturday Night Live’s Kristen Wiig about a luckless woman (Wiig) who’s asked to serve as maid of honor at her best friend’s (Maya Rudolph) wedding. What was deemed at the time to be a commercial risk — Will audiences see a female-driven broad comedy? was actually a thing industry insiders used to wonder — proved to be ground zero for many of modern comedy’s biggest talents. Bridesmaids didn’t just cement Wiig and Feig’s film careers, it also paved the way for Damages’ Rose Byrne’s second life as Hollywood’s go-to hilarious sidekick and Melissa McCarthy’s ascension to the A-list. (And don’t forget the star-making turns from Chris O’Dowd and Ellie Kemper.) Though only Bridesmaids’ producer, Apatow oversaw a movie that merged the outrageous laughs and just-hanging-out vibe of his own films with Wiig’s clear eye for the complexity of female friendships and her fascination/revulsion with getting-to-the-altar romantic comedies. Bridesmaids is great because it’s funny and sweet and silly and surprisingly touching: the Apatow aesthetic perfected.

Grierson & Leitch write about the movies regularly and host a podcast on film. Follow them on Twitter or visit their site.

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