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This article has been updated to include Apatows recent films, including this weeks 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.

Its 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 Hollywoods 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 theyd one day find a good girl and settle down. Over time, Apatows approach has matured and grown more sophisticated, but that core pleasure remains.

To celebrate Apatows growing oeuvre, were ranking the best of his movies. But first, some ground rules. Because wevealready chronicled the highs and lows of Ferrells career, were leaving off the movies they made together:Anchorman,Anchorman 2,Step Brothers,Talladega Nights,andKicking & Screaming. And were also skippingBegin Again, the Keira KnightleyMark Ruffalo musical drama that Apatow produced because, frankly, its so thematically and tonally removed from the Judd Apatow Cinematic Universe were not entirely convinced IMDb isnt 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 its 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 Apatows 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 Ramiss 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, its 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 doesnt 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 theyre going to lose to Utah in the NBA Finals, kidnap the Jazzs 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 doesnt 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 Pridecame out a month before The Cable Guy,delivering aone-two punch to Apatows 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 Wilsons first films after recovering from his 2007 suicide attempt. That timing didnt 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 Superbads combo of boisterous adolescent laughs and unexpected sweetness. Apatows wife, Leslie Mann (a constant bright spot in his films), has some flirty fun as Wilsons 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 its still frustrating a decade later. This remake of the 1977 comedy follows an upper-middle-class couple (Jim Carrey and Ta 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. Its 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 Brands 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, Hills bread and butter was playing shlubby dorks in broad comedies, and dramatic actress Rose Byrne (whos hilarious as Snows pop-star girlfriend) hadnt yet figured out that she was one of her generations greatest comedic dynamos.

19. Juliet, Naked (2018, producer) Apatow has worked on a lot of films about immature men, but director Jesse Peretzs adaptation of a Nick Hornby novel shows what happens when the execution falls flat. Chris ODowd plays Duncan, a superfan of a faded fringe singer-songwriter (Ethan Hawke). Duncans 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 its also fatally adorable in how it depicts these mismatched characters and their ho-hum problems. As a result, this tame date movie isnt nearly as anarchic or wise as Apatows 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 neighbors house while he shows you pictures of his familys vacation to suburban Los Angeles. The Wealthy, White Ennui is oppressive throughout, but the worst part is that the movie isnt even funny. This is Apatow out of ideas and just grabbing at everything in arms reach; this is Apatow as that date who never asks you any questions about your life. And its nearly two-and-a-half hours long!

17. You Dont 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 Dont Mess With the Zohan is a grenade hurled clumsily at politically correct watchdogs, mocking both sides of the Israeli-Palestinian conflict when its not making obvious jokes about randy middle-aged women or giddily spoofing action-movie tropes. But commendable only gets you so far, and Zohans hit-to-miss joke ratio is, well, about as good as any of Sandlers lazy mainstream comedies. That said, wed support any Kickstarter effort to finance a spinoff film focusing on John Turturros nutso terrorist character.

16. Wanderlust (2012, producer) One of those cases where a lot of funny people get together and the sparks just dont fly, Wanderlust unites directorco-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 Rudds character try to talk dirty for 90 minutes.

15. May It Last (2017, director, producer) Apatows 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, youll love this movie; May It Last is made with a gentle fans 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 dont know the band, youll be on the outside looking in. Apatow loves the Avett Brothers, and why not? Theyre a great band. But thats mostly all the movie has to say. Still, were 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 wont 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 doesnt 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 worlds 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 Carreys psychotic cable guy and Matthew Brodericks milquetoast dweeb. The Cable Guy isnt always funny but its 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 didnt 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 thats a staple of Apatow films works, partly because Segel plays him so winsomely, and mostly because hes written so sincerely. Not everything about the Mila Kunis character works shes 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) arent top-shelf Lonely Island, and the celebrity cameos provide diminishing returns each time a new one shows up. Its still funny almost an updated, less movie-obsessed Walk Hard, with Andy Samberg and company satirizing musical genres one suspects Apatow doesnt listen to a lot of. One thing the Lonely Island guys and Apatow have in common (other than penis insecurity): Theyre all good-hearted, gentle satirists, so while the laughs come at you fast, theyre 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 Apatows longest film as a director the overstuffed two-and-a-half-hour epic he had the clout to make only after Knocked Ups 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, its 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 its 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 youre 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) Heres where Apatow confidently enters his veteran-comedic-filmmaker period, smoothly directing Amy Schumers script about a commitment-phobic mens-magazine writer (Schumer) who falls for a good guy (a superb Bill Hader). Trainwreck is the sort of New Yorkset 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 whos who of reliable comedic supporting players everyone from Vanessa Bayer to Randall Park to Jon Glaser are a constant delight. This is one of Apatows most polished and mature film, which doesnt mean there isnt 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 Islandreally does show a legitimate evolution for Apatow, and a desire to grow. Ironically, thats because his focus this time is on a kid named Scott (Pete Davidson, who co-wrote based on his own life story) who isnt just in a state of arrested development; hes truly, profoundly damaged. That tension, between Davidsons pain and stubborn resistance to change and Apatows traditional coming-of-age, givesThe King of Staten Islandsome real dramatic friction, making it a compelling watch even when Apatow, as usual, wanders off course occasionally. (He wouldnt be our first pick to direct an attempted robbery thats 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 Scotts 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 doesnt 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 Apatows movies havent 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 2017s 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 Emilys 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 nonSpring Breakers performance hell 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 Were 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 its consistently raucous enough that the sneaky sentiment surprises you. And its a sure bet that, eight years later, a lot of people still think Christopher Mintz-Plasses 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, Apatows 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 Apatows screenplay is full of texture and heartfelt observations: how nobody ever really feels like an adult, how life is what happens when youre busy making other plans, whether Steely Dan are incredible or gargle balls. Watch Knocked Up now, and theres 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 Apatows 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 youre gay? battle between Paul Rudd and Seth Rogen seems to sum up every white heterosexual teenager weve 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)Apatows 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 Lives Kristen Wiig about a luckless woman (Wiig) whos asked to serve as maid of honor at her best friends (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 comedys biggest talents. Bridesmaids didnt just cement Wiig and Feigs film careers, it also paved the way for Damages Rose Byrnes second life as Hollywoods go-to hilarious sidekick and Melissa McCarthys ascension to the A-list. (And dont forget the star-making turns from Chris ODowd 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 Wiigs clear eye for the complexity of female friendships and her fascination/revulsion with getting-to-the-altar romantic comedies. Bridesmaids is great because its funny and sweet and silly andsurprisingly touching: the Apatow aesthetic perfected.

Grierson & Leitch write about the movies regularly andhost a podcast on film. Follow them onTwitteror visittheir site.

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The Best Judd Apatow Movies, Ranked - Vulture