Judd Apatow’s mark on the comedy landscape cannot be overstated. With 2005’sThe 40-Year-Old Virginhe 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 likeSeth Rogen,Jason Segel, andKristen 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 withFunny Peopleis 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 ofFunny Peoplefeels like a completely different movie that loses the thread of whatever this story was supposed to be about (andSeth Rogenis pushed into the “just along for the ride” role). Clearly the film’s tone and narrative structure are influenced by the somewhat meandering work ofJames L. Brooks, but that’s a tightrope walk that even Brooks has fumbled (remember the incomprehensibleHow Do You Know?).
But there are things to like aboutFunny People.Adam Sandlergives 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 thePete HolmesHBO seriesCrashing.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 aboutallof 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 40is 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 thanFunny Peopleand 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 40is 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, butThis Is 40actually 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 ofThe 40-Year-Old Virginwas no easy task, but credit to Apatow for refusing to try and make the same film twice.Knocked Upis in some ways more of a traditional romcom than40-Year-Old Virgin, albeit one that seeks to hone in on some of the striking differences between men and women in relationships.Katherine Heiglpretty publicly lambastedKnocked Upfor painting the women as “shrews,” which I don’t entirely think is fair. I first sawKnocked Upas 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 Upis 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. ButThe King of Staten Islandis probably Apatow’s most dramatic film yet, and all the better for it. Just asTrainwreckallowedAmy Schumerto bare her soul,The King of Staten Islandis semi-autobiographical asPete Davidsonstars 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 cinematographerRobert Elswitto 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 regardTrainwreckis the one that really stands a cut above. It’s also the first of Apatow’s films since40-Year-Old Virginthat is essentially someone else’s story, after mining his own life for inspiration forKnocked Up,Funny People, andThis Is 40. Here, Apatow encouragedAmy Schumerto 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-actorLebron James, who steals a number of scenes.
What makesTrainwreckone 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,Trainwreckreally 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 cinematographerJody Lee Lipesbrings 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 puttingThe 40-Year-Old Virginat #1. The film still (mostly) holds up really well, while acknowledging that the transphobic and homophobic jokes are tough to stomach. But what really madeThe 40-Year-Old Virginsuch a smashing success wasSteve 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 throughout40-Year-Old Virgin(and all of Apatow’s films, really) that makes it endure. You want only good things for Andy.
Indeed, whileThe 40-Year-Old Virginis 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.
