This month marks the 10th anniversary of The 40 Year Old Virgin, one of the best comedies of the 2000s and the directorial debut of Judd Apatow. In the decade since the film’s release, Apatow has become one of the biggest names in comedy, writing, directing and producing some of the funniest movies in years. And Apatow shows no sign of slowing down, already directing his fifth film, Trainwreck, and releasing his first book, Sick in the Head, this year. On this anniversary of The 40 Year-Old Virgin, let’s look back on over 20 years of Apatow and rank the comedy impresario’s achievements.
20. You Don’t Mess With the Zohan (2008) – Co-writer
In all fairness, You Don’t Mess With the Zohan isn’t as bad as you probably imagine it to be. It’s no masterpiece, but thanks to a script by Apatow, Adam Sandler and Robert Smigel, Zohan does get more laughs than it probably deserves, in a story that should probably be the length of an SNL skit. Coming near the end of Sandler’s “ehh-it’s-not-great-but-it’s-somewhat-fun” period, Zohan tell a story as old as time, about a Israeli Special Forces soldier that moves to New York City to become a hair stylist. Zohan is about as one-note as you can get, but the note is at least occasionally amusing.
19. Celtic Pride (1996) – Writer
Even in Apatow’s earliest films, you can see an interest in the underdog rising up and attempting to become something greater than they are. Thankfully though, this theme would get funnier after Celtic Pride, which stars Daniel Stern and Dan Aykroyd as two frustratingly obsessed sports fans and, somewhat inexplicably, casts Damon Wayans in what is essentially the straight man role. No one is at their best here and the tone—which is all over the place—never quite manages to make dark comedy actually all that funny.
18. Heavy Weights (1995) – Co-writer
Heavy Weights is one of the many films that is beloved almost solely because of people’s affection for it from watching it as a child. Coming a year after the superior Camp Nowhere, Heavy Weights also shares Apatow’s love for the underdog, but unfortunately it too often feels like the punchline is that these kids are little fat guys. Beyond nostalgia, Heavy Weights is worth watching for fun early performances by Paul Feig and Kenan Thompson, a pretty hilarious role played by Ben Stiller (in what is clearly a first draft character that would be perfected in Dodgeball), and not much else, despite its good intentions.
17. Fun With Dick and Jane (2005) – Co-writer
Before going to write some of the best comedies of the last decade, Judd Apatow and Nicholas Stoller wrote Fun With Dick and Jane, an adaptation of the 1977 film of the same name, set during the financial crisis of the time. As a married couple that have lost their jobs and all their money, Dick and Jane (Jim Carrey and Tea Leoni) decide to become thieves, specifically targeting the head of the now-defunct company that put Dick in this situation. The only problem is that despite its title Fun With Dick and Jane just isn’t all that fun. Fun With Dick and Jane ends up being far more bland than promised, especially considering the team in front of and behind the cameras.
16. The Ben Stiller Show (1992-1993) – Writer and co-creator
On the commentary track for The Ben Stiller Show, Stiller admits to Apatow that his FOX show likely should’ve been on HBO instead. Watching the show 20 years after it originally aired, the episodes do have a dated quality, often parodying FOX’s biggest shows at the time, like Melrose Place and Married…With Children. But The Ben Stiller Show does have a phenomenal cast of future greats at the beginning of their careers, with Stiller, Andy Dick, Janeane Garofalo and Bob Odenkirk all showing early promise that would later pay off in spades.
15. The Critic (1994-1995) – Writer, 2 episodes
Apatow’s first animated credit makes perfect sense, as The Critic’s Jay Sherman is just the sort of lovable schlub that Apatow would later become famous for creating. In Apatow’s first episode, “Marathon Mensch,” Jay is tired of being seen as a loser in the public’s eye, so he participates in a marathon. Of course, Jay takes longer than anyone else to finish the race, but it’s his determination to actually finish that makes Jay the hero of the episode. Apatow knew how to get to the core of what makes Jay worth rooting for and, by doing so, wrote two of the show’s best episodes.
14. Pineapple Express (2008) – Story
It’s hard to believe, but there was an entire decade between Seth Rogen and James Franco’s first project together, Freaks and Geeks, and their next, Pineapple Express. Written by Rogen and Evan Goldberg with a story by Apatow, Pineapple Express turns the action-comedy on its head by adding weed. Rogen and Franco’s chemistry is fantastic here and would only improve in their later films. Plus, nothing can beat Pineapple Express 2 from This Is the End.
13. The Late Late Show (2015) – Host, 2 episodes
When Craig Ferguson left The Late Late Show, the temporary opening was filled by an interesting series of guest hosts. While the results were hit-or-miss (The Talk’s co-hosts don’t need more than one program a day, but someone give Adam Pally a talk show immediately), Apatow fit right in. Having interviewed comedians for years, Apatow had a natural rapport with guests like Adam Sandler, Lena Dunham and former boss Garry Shandling as well as bringing a nice personal touch. If the networks are ever looking for yet another white guy to host a late night show, Apatow would be a great choice.
12. The Simpsons (2015) – Writer, 1 episode
Everyone always complains that The Simpsons just isn’t as good as it used to be, but with his sole episode, Apatow brought the show back to what made it so great in the first place. “Bart’s New Friend,” an episode Apatow wrote 25 years before it actually came to air, has Homer Simpson getting hypnotized into thinking he’s a 10-year-old, with the hypnotist getting arrested before he can reverse the effects. “Bart’s New Friend” is the rare recent episode that focuses on the relationship between the various family members, as Bart finds a new best friend, Marge loses her lover and Lisa finds her father at his most supportive. Apatow’s strong understanding of what makes this family so interesting results in one of The Simpsons’s finest episodes in years.
11. This Is 40 (2012) – Writer and director
By 2012, Apatow was synonymous with consistently great comedy. With this is This Is 40, however, he put so much of himself into the movie it didn’t quite resonate with audiences the same way that his past films had. Yet This Is 40 is fascinating in its realness, as the arguments between Paul Rudd and Leslie Mann feel like they were almost dictated from actual fights. Just like all relationships, This Is 40 has moments of darkness and pain that make the levity even better when you get to them.