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The 2020 dramedy The King of Staten Island marks the sixth feature film for director Judd Apatow, and stars Saturday Night Live cast member Pete Davidson as a fictionalized version of himself. But where does the new movie fit in the filmmaker’s accomplished resume?
Fifteen years ago, The 40-Year-Old Virgin established Apatow as one of cinema’s exciting new voices — this coming after he’d previously directed episodes of The Larry Sanders Show and the short-lived Freaks and Geeks starring Linda Cardellini, James Franco, and a young Seth Rogen. Apatow then created the Fox series Undeclared featuring a pre-Sons of Anarchy Charlie Hunnam. Later, when The 40-Year-Old Virgin performed well at the box office and Knocked Up became another critical/commercial success in 2007, Apatow seems to be the “next big thing” in the world of raunchy yet poignant comedy films. In the past 15 years, the director’s thematic approach has evolved with adult-oriented productions like Funny People and This Is 40.
The following list doesn’t including the recent Apatow-directed documentaries May It Last: A Portrait Of The Avett Brothers and The Zen Diaries of Garry Shandling. Instead, the focus is primarily on his six features. Here’s a complete ranking of Apatow’s films from worst to best.
Written by and starring Amy Schumer, Apatow’s 2015 film Trainwreck feels like a misstep in the director’s oeuvre. On paper, the casting makes sense, as both Schumer and co-star Bill Hader were ideal choices based on their industry momentum at the time. But whereas Apatow’s early comedies feature situational comedy that feels bizarrely natural, much of Trainwreck’s humor feels stiff and awkward, with many of the jokes correlating with played-out genre tropes. There’s the opening bedroom sequence with the usual contrived snoring; a failed opportunity to effectively “hook” the audience. Trainwreck features a memorable supporting performance from NBA icon LeBron James, but many of his scenes similarly feel comedically forced, and imply that Apatow and company are more interested in accessible pop culture references than sharp comedy.
Curiously, Hader doesn’t receive strong comedic material in Trainwreck. Portraying Dr. Aaron Conners, the romantic interest of Schumer’s Amy Townsend, he never really strays from the Kind Doctor archetype. Incidentally, Hader doesn’t have the mystery of his Barry character, nor does he give the impression that he was once a standout cast member on Saturday Night Live. He’s just OK, much like the script. Schumer similarly gives a decent performance, one that’s weighed down by questionable jokes about race and scenarios that are more cute than comedic.
With This Is 40, Apatow played it safe by directing a Knocked Up spinoff. The film stars his endearing wife Leslie Mann and the perpetually-likable Paul Rudd, both of whom reprise their roles as the always-bickering parents Debbie and Pete, respectively. Apatow wrote the script for This Is 40 himself, giving the story an authentic feel with comedy that feels organic. There’s nothing inherently wrong with This Is 40 during the first 90 minutes, but Apatow then tries to squeeze in some extra depth with a final act that’s simply too dragged-out.
Apatow wisely connects Debbie and Pete’s personal issues to their parents. It’s always a good move to incorporate John Lithgow and Albert Brooks as characters who enliven regular conversations with one-liners and physical comedy. But although This Is 40 includes strong messages about inherited trauma and familial psychology, Apatow unfortunately takes a heavy-handed approach, resulting in a didactic final act. On one level, it works for the premise, but Apatow also seems invested in letting audiences know that he’s really growing up and learning valuable life lessons. That’s fine, but it’s something the audience can grasp without hammering away at the concept.
Another nostalgia-driven Apatow production, Funny People stars none other than Adam Sandler as a fictionalized version of himself. The screenplay, written solely by Apatow, caters to the Sandman’s comedic palette of zany voices and includes meta references to his pop culture persona. Interestingly, Apatow adds a cancer-themed subplot that allows for a moving commentary about legacy, and also affords co-star Seth Rogen to display his full skill set. There’s a distinct mentor-protege dynamic between George Simmons (Sandler) and Ira Wright (Rogen), and the film ultimately succeeds by focusing heavily on their give-and-take relationship.
With Funny People, Apatow provides audiences with a smart commentary about the stand-up comedy circuit, all the while adding extra layers about interpersonal relationships and Hollywood power dynamics. Supporting players like Eric Bana and Jason Schwartzman give sharp character portrayals, while Mann sticks to her usual brand of passive-aggressive comedy as Laura. Funny People is a safe Apatow film, but one that takes risks, at the right spots, with edgy dialogue and existential themes. What does one do upon accepting imminent death and then learning that life will go on as normal? Apatow doesn’t imply that he has all the answers, but rather suggests that sometimes you just need to shut up, listen to others, and take a deeper at look at who you want to be.
For Apatow’s feature debut The 40-Year-Old Virgin, he enlisted Steve Carell as his co-writer and horny lead. From beginning to end, there’s a potent one-liner in each minute of the film, with Carell himself carrying the storyline with his impeccable comedic timing and ability to convey social anxiety in almost every situation. With this narrative rock in place, co-stars like Rogen and Rudd can play it natural, knowing full well that they can improvise and bounce jokes off Carell.
At its core, though, The 40-Year-Old Virgin isn’t about having sex — it’s about finding the right romantic partner to have sex with. In that sense, Catherine Keener gives the film more depth, as her character Trish can’t quite figure out Carell’s Andy. The underlying message about honest communication lays the groundwork for clever scenarios, most notably when Andy tries to protect his virginal secret during a card game with his male colleague, or when several of the supporting characters lash out at work. By flipping the script on the premise by having Andy pretend to be a sex-hungry Bro type, The 40-Year-Old Virgin effectively addresses misconceptions about how men and women are supposed to act while pursuing relationships. And with supporting performances from female actresses like Leslie Mann, Elizabeth Banks, Jane Lynch, and Kat Dennings, Apatow shows that he’s interested in exploring differing perspectives.
Five years after Trainwreck, Apatow returned to form with The King of Staten Island, a film that favors the central story over directorial gimmicks and nostalgia. Pete Davidson portrays a fictionalized version of himself as Scott, a wannabe tattoo artist who just can’t catch a break — or a least that’s how it seems. Much like Funny People, it’s the focal character’s introspection that grounds the film, which leaves Davidson to either sink or swim with his lead performance. Fortunately for audiences, Davidson doesn’t stick to the Millenial Stoner persona that he conveys on Saturday Night Live, but instead embraces the darkest aspects of his character, specifically the fact that he can’t get over his father’s death 17 years prior. Scene by scene, The King of Staten Island deconstructs the protagonist’s defense mechanisms, building to a second half that’s more about character psychology than traditional comedy.
And that’s what makes The King of Staten Island so intriguing, as it’s arguably the least funny Apatow film. Stand-up comedian Bill Burr co-stars as a fireman named Ray, and even he’s more invested in a dramatic character performance instead of mixing in comedic jabs as Scott’s enemy-turned-mentor. In real life, Davidson’s father passed away on 9-11, but the audience doesn’t need to know that bit of information to appreciate Apatow’s film. Without any context, The King of Staten Island holds up as timely character study about someone who desperately needs help, but doesn’t quite understand how to communicate that. When Scott stops performing for others and just unloads his inner feelings, that’s when Davidson displays his true depth as a performer.
After The 40-Year-Old Virgin, Apatow took a strong step forward with Knocked Up. Starring Rogen and Katherine Heigl as an unlikely couple, the 2007 comedy maintains a comedic and dramatic balance, and through the lens of American 20-somethings. As a filmmaker, Apatow appears to be clinging to his younger years while realizing that everything is about to change upon becoming a father. He acknowledges this concept though a subplot involving his own wife and kids (and through Rogen’s character, of course), all the while having fun with Stoner material that’s ideal for his male lead as Ben Stone.
Knocked Up is a complete Apatow film. The director pays special attention to tone, specifically in how he shifts from sex jokes to conversations about the consequences of sex. As a character, Ben is somewhat similar to The King of Staten Island’s Scott, only he’s far less perceptive about the world around him. In contrast, Heigl’s Alison is incredibly self aware as a television personality. By once again considering differing gender perspectives, Judd Apatow makes Knocked Up a universally-relatable film with its fundamental message about relationships and parenthood. It’s not a character study about one specific person, but rather a cultural commentary about change. And when the story moves away from Ben and Alison, the A+ supporting cast continuously picks up the slack.
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