Judd Apatow’s mark on the comedy landscape cannot be overstated. With 2005’s The 40-Year-Old Virgin he ushered in an entirely new style of comedy. One marked by improvisation, long takes, and lacking in huge recognizable stars. This “grounded” approach was immediately embraced by audiences and kicked off a slew of imitators, all while Apatow produced and helped shepherd the individual voices and careers of folks like Seth Rogen, Jason Segel, and Kristen Wiig, among many others.

But looking closer at the films that Apatow directed himself is fascinating. There’s a common thread among them all—a balance of R-rated humor with sincere emotion—but as the years go on, Apatow tries to push closer into drama territory while changing up his cinematic style a bit. And with Apatow’s latest effort, The King of Staten Island, releasing this Friday on VOD now felt like a good time to revisit and rank all of Apatow’s films.

[Editor’s note: While Apatow’s documentaries are excellent—particularly The Zen Diaries of Garry Shandling—this list is focused only on his narrative feature films.]

6. Funny People

Even Judd Apatow’s worst movie has some fascinating stuff in it. The problem with Funny People is that it’s two different movies smashed together. On the one hand, you have a kind of dark comedian mentor/protege story steeped in the world of stand-up. On the other hand, you have a kind of dark romantic comedy in which a guy goes back for who he feels is the love of his life in very icky fashion. And in practice, the whole third act of Funny People feels like a completely different movie that loses the thread of whatever this story was supposed to be about (and Seth Rogen is pushed into the “just along for the ride” role). Clearly the film’s tone and narrative structure are influenced by the somewhat meandering work of James L. Brooks, but that’s a tightrope walk that even Brooks has fumbled (remember the incomprehensible How Do You Know?).

But there are things to like about Funny People. Adam Sandler gives a really interesting performance as basically a heightened, dirtbag version of himself who tries (and fails) to become a better person. And Apatow is clearly passionate about the comedy world and the dynamics at play between comedians, which is something I think he more successfully navigated in the Pete Holmes HBO series Crashing. It’s just that when you put all of this together, the script is unable to really dig deep into any one thing because it’s trying to be about all of these things at once. A misfire, but an admirable one nonetheless.

5. This Is 40

Quite likely Judd Apatow’s most personal film, The Is 40 is also one of his most complicated. There’s the “rich white people problems” issue that taints the whole affair and the fact that the characters are largely miserable for much of the running time, but the film is also narratively much tighter than Funny People and by golly, Paul Rudd and Leslie Mann are charming as hell in the lead roles. I both hate and kind of like this movie. It’s not necessarily a fun time to watch this married couple bicker for almost the entire runtime while also yelling at/about their kids, but there’s an undercurrent of truth there—anyone who’s been in a long-term relationship or marriage knows that in order for that relationship to last, both partners have to put in the work. This Is 40 is basically about a breaking point in this central relationship, in which the two characters must individually realize the kind of work that’s necessary to make this marriage last. And that work involves understanding the private battles that each partner is suffering, and empathizing with that.

But again, the specifics of the conceit make it a little hard to empathize. They live in a big nice house, the husband owns his own record company, and the “fix” to their money problems is literally “ask Ryan Adams to sign to your label.” And while the notion of a marriage straining is a universal concept, the actual act of spending over two hours with two people constantly frustrated and annoyed by one another can test one’s patience. The film could have used with a bit more of a show of how Pete and Debbie actually love one another.

The narrative, however, is less prone to meandering than Apatow’s earlier films, and the jokes feel more pointed rather than leaning on run-on improvisational humor. Funny People’s attempt at drama largely falls flat, but This Is 40 actually works better in the dramatic areas, largely thanks to Mann’s genuinely fantastic performance as a complicated woman.

4. Knocked Up

Following up the smashing success of The 40-Year-Old Virgin was no easy task, but credit to Apatow for refusing to try and make the same film twice. Knocked Up is in some ways more of a traditional romcom than 40-Year-Old Virgin, albeit one that seeks to hone in on some of the striking differences between men and women in relationships. Katherine Heigl pretty publicly lambasted Knocked Up for painting the women as “shrews,” which I don’t entirely think is fair. I first saw Knocked Up as a teenager and, understandably, found myself identifying with Ben and his goofy-ass friends. But revisiting the film as a thirtysomething, I do think Apatow’s intent here was to highlight the lazy and juvenile nature of Ben and his buddies. Yes, they’re played for laughs quite often, but ultimately when Alison’s due date is approaching, Ben is clearly acting irresponsibly and Alison and Debbie (Leslie Mann) are the only two people taking this seriously, not as shrews but as adults. It’s also striking that Ben gets his act together despite the fact that Alison and him have broken up—he get a place of his own and start reading baby books to try and win Alison back, he does it because it’s the right thing to do.

Granted, the film does lean heavily on the “manchild” antics for laughs, including an unnecessary drug trip in Vegas, so it doesn’t entirely come down on them too hard. But the laughs play for the most part, aside from the jokes that have aged rather poorly. Knocked Up is really funny, while ultimately landing in a really emotional place with the birth of Ben and Alison’s child. There are shades of drama here that Apatow would more fully explore in later films, but ultimately the mix of lewd humor and sincere heart works pretty well in this one.

3. The King of Staten Island

Apatow’s latest film, The King of Staten Island, is really his next evolution as he’s been blending comedy with drama since the beginning of his career. But The King of Staten Island is probably Apatow’s most dramatic film yet, and all the better for it. Just as Trainwreck allowed Amy Schumer to bare her soul, The King of Staten Island is semi-autobiographical as Pete Davidson stars in, co-writes, and produces the story of a Staten Island twentysomething struggling with malaise, mental illness, and anxiety—much of which stems from the death of his father. When his mother (Marisa Tomei) starts dating a fireman (Bill Burr), Davidson’s character is forced to confront unresolved issues head-on.

And it’s quite good! Davidson is really terrific in the lead role, and Apatow steers the dramatic tone of the piece pretty well. It does tend to meander here and there, as is Apatow’s style, and takes a bit to find its central plot thread. But I suppose that’s part and parcel with its protagonist, who is similarly directionless. The film is also one of Apatow’s most cinematic efforts, working with cinematographer Robert Elswit to craft a visually pleasing palette that’s also naturalistic.

2. Trainwreck

An argument could be made that almost all of Apatow’s films are some version of a romantic comedy, and in that regard Trainwreck is the one that really stands a cut above. It’s also the first of Apatow’s films since 40-Year-Old Virgin that is essentially someone else’s story, after mining his own life for inspiration for Knocked Up, Funny People, and This Is 40. Here, Apatow encouraged Amy Schumer to get deeply personal, and so she does. This is the story of a woman with commitment issues, family issues, and father issues who begins to rethink aspects of her life after starting up a relationship with a mild-mannered doctor (Bill Hader). Schumer knocks the lead performance out of the park, nailing the comedic and dramatic beats equally. And in an inspired bit of casting, Hader is a tremendous romantic lead here. Sensitive and reassuring, but also deeply funny. Apatow also works his magic with non-actor Lebron James, who steals a number of scenes.

What makes Trainwreck one of Apatow’s best, however, is its focus. This film isn’t prone to the narrative side roads that can make some of his other films feel overlong and tedious. With its complexly drawn protagonist, Trainwreck really follows one single story from beginning to end, and it’s wildly compelling. The film is also a huge step up visually from Apatow’s previous films, as cinematographer Jody Lee Lipes brings a textured, almost nostalgic quality to the frame. Apatow has long been a champion of other voices as a producer, so it’s no surprise he’s able to craft a terrific film as a champion of someone else’s story (and script) as a director.

The 40-Year-Old Virgin

But ultimately, it’s hard to resist putting The 40-Year-Old Virgin at #1. The film still (mostly) holds up really well, while acknowledging that the transphobic and homophobic jokes are tough to stomach. But what really made The 40-Year-Old Virgin such a smashing success was Steve Carell. Many forget he co-wrote the script with Apatow, and so Andy is as much his creation as he is Apatow’s. And it’s Carell’s insanely likable sensibility and empathic qualities that make Andy a character worth rooting for. As outlandish as the jokes may get, there’s an undercurrent of heart throughout 40-Year-Old Virgin (and all of Apatow’s films, really) that makes it endure. You want only good things for Andy.

Indeed, while The 40-Year-Old Virgin is a sex comedy, it’s really a film about men’s ridiculous notions of sex and relationships. Andy spends most of the movie taking advice from his co-workers on how best to find “the one,” which range from offensive to insane. And by the movie’s end, Andy finds love with Trish ultimately by being himself—his nerdy, goober self—while his co-workers are still, notably, single. This movie doesn’t glorify the behavior of David, Jay, and Cal, it highlights how dumb it is.