All of Judd Apatow’s Movies, from ‘Funny People’ to ‘The Bubble,’ Ranked

9. “The Bubble” (2022)

It was difficult to fully appreciate how long we’d been living with COVID until Apatow made an unfunny comedy about it that was set in 2020, released in 2022, and felt like it was roughly 9,000 years old. Set on a quarantined blockbuster film shoot during the height of the pandemic, and released more than two years into a global crisis that continues to surprise us with fun new twists every time we get cocky, “The Bubble” crystallizes the unique pain of watching a woefully dated satire about the same pandemic you’re still trying to outlast. 

Apatow gets a lot of shit for making scattershot comedies that run the length of David Lean epics, but the patchwork of scenes that comprise “The Bubble” — which clocks in at two hours that each feel like 10 — have less in common with “This Is 40” than they do “Movie 43,” and might just be aimless enough to make the director’s critics appreciate the flow of his earlier work. The occasional bit lands well enough that it can be tempting to see the film’s erratic mishmash of unrelated jokes as a stir-crazy expression of our collective lockdown cabin fever, but Apatow’s film is never intentional enough to escape the same “just be glad we made something for you” sense of Hollywood self-importance that it’s ostensibly trying to skewer.

Despite the usual generosity with which Apatow uses his platform to highlight a wide range of new comic talents from around the world (including “Borat 2” breakout Maria Bakalova and social media star Harry Trevaldwyn), “The Bubble” proves ironically difficult to appreciate on its own terms. —DE

8. “This Is 40” (2012)

Essentially a feature-length version of off-handedly muttering to a pal that “being an adult is hard, huh?,” “This Is 40” mainly rankles because there is so much good material, real insights, and extremely funny jokes (read: pretty much any line reading performed by the exceptionally talented Leslie Mann, a star who can make even whining over wanting to go to the movies a full-force howler) trapped in the middle of an overall scattershot feature.

But, oh, isn’t that so much like life itself, huh? Sure, but Apatow and his crew have approached similar material before with much better results, from its predecessor “Knocked Up” to his opus “Funny People.” While “This Is 40” occasionally hits on moments of transcendence — getting high and debating different ways you want to kill your spouse, with your spouse, being chief among them — so much of the film feels cobbled together from other outings and better ideas. Yes, being an adult is hard, but comedy about it shouldn’t feel just as painful. —KE

7. “Trainwreck” (2015)

There’s little middle ground with Apatow films — they’re either stone-cold classics from the moment they arrive on the big screen (“Funny People,” “The 40-Year-Old Virgin,” “Knocked Up”) or they’re of-the-moment curios that seem destined to be forgotten (or, even worse, reevaluated) almost immediately. “Trainwreck,” for all its star-making power (it effectively pitched both Amy Schumer and Bill Hader as charming, messy romantic leads, while making the case for LeBron James as an untapped comedic gem and reminding everyone how goddamn funny Tilda Swinton is), falls firmly into the latter category.

While it’s rife with plenty of the usual Apatow obsessions, from gross-out gags (zzz) to a real darkness at its heart (Schumer’s Amy Townsend is an alcoholic who blows up her life on the regular), there’s something about the entire affair that feels dated, right out of the gate. Partially based on Schumer’s own life, the film doesn’t suffer from a shortage of honesty, but there’s also the sense that we’ve seen all this before — and done better — by nearly everyone involved with the film. —KE

6. “May It Last: A Portrait of the Avett Brothers” (2017)

With most behind-the-scenes, making-of music docs, you can feel something ominous in the air. Either the artists on display are on the verge of a schism or someone’s personal life is threatening to undo the collective goals of the group. “May It Last,” a documentary from Judd Apatow and Michael Bonfiglio about the North Carolina-based folk-rock group The Avett Brothers, never stumbles on that central, driving conflict. Instead, the film presents the story of two brothers, Scott and Seth Avett, who have lived their separate lives without being fueled by the need to bring seismic change to the music industry or each other.

“May It Last” still places The Avett Brothers in the context of a musical quest but finds an equally satisfying path in the ordinary elements of their lives. The doc recognizes that The Avett Brothers aren’t trailblazers. The music that they play feels at home in a few different genres and the brothers themselves would likely admit that they’re not rewriting the formula for how to make a relatable song of joy or loss.

What “May It Last” does get across is how this musical partnership is able to so potently harness the power of the everyday. It’s strong proof that a film about a band can still be captivating even if it seems destined to end in a giant group hug. —SG

5. “The King of Staten Island” (2020)

Judd Apatow’s work bears any number of personal signatures, but it boils down to the two things he loves most of all: Overlong movies about overgrown man-children, and helping commercially unproven comedians become huge stars by making films and HBO shows in which they embody lightly fictionalized versions of themselves. Needless to say, an 140-minute dramedy starring and about “SNL” breakout Pete Davidson — a tabloid-famous stoner who once bragged on national television about still living with his mom — is as Apatow as it gets.

Teetering between self-parody and something truly beautiful, Apatow’s semi-biographical comedy about a stunted outer-borough stoner who’s still grieving the loss of his firefighter dad offers yet another of the director’s shaggy portrait of permanent adolescence, but this one helps make sense of why he always keeps going back to the same archetype. Davidson is compulsively watchable, Marisa Tomei and Bill Burr are outstanding as his mom and her new boyfriend, and the patience with which Apatow pushes all of these characters forward feels like a genuine form of love.

If “The King of Staten Island” lacks the lightning-in-a-bottle magic that made Apatow’s first movies such instant cultural touchstones, this sweet film compensates for that by how poignantly it crystallizes the feeling of being too afraid to escape your own shadow. —DE

4. “The Zen Diaries of Garry Shandling” (2018)

Garry Shandling was widely recognized for his comic genius in his own time, but Apatow’s documentary about his late friend and mentor doesn’t merely focus on the legendary career that fans already know by heart. Using a chronological approach, Apatow outlines how Shandling’s work was in many ways intertwined with the personal life that few people got to see. So while this 4 1/2 hour film feels like a career overview for a man who was both loved and misunderstood, it’s also a rare tribute movie that’s interested in discovering what the filmmaker didn’t know before the project started (“In many ways, he was a mystery to me,” Apatow confesses at one point). 

So when the on-camera interviews with Shandling’s friends, family, and colleagues come in the form of conversations with Apatow, it feels less like a documentary and more like catch-up chat at a funeral that’s happening two years after Shandling’s death.

As a tribute, a eulogy, and an appreciation, “The Zen Diaries” is an even-handed look at someone who sought to bring meaningful change into other people’s lives as he searched for that same sense of fulfillment himself. Even if the film didn’t actually include footage from a ceremony remembering and celebrating Shandling’s life, it would make you feel like you were already part of one. —SG

3. “Knocked Up” (2007)

Judd Apatow flirted with the rom-com formula in “The 40-Year-Old Virgin,” but it wasn’t until “Knocked Up” that he went all in on the genre, reluctantly dragging the genre into the 21st century by capitalizing on the happy accidents of hookup culture. Apatow’s script hinges on the oldest of dynamics: A battle of the sexes between a man and woman from opposite social circles. Here, Ben Stone (Seth Rogen in his first starring role) is a total burnout who spends his days trying to invent Mr. Skin with his stoner housemates, and Alison Scott (Katherine Heigl) is a high-powered E! correspondent who’s just been promoted to on-air talent.

The war between them is locked into a stalemate from the moment it starts, as Alison gets pregnant from their one-night stand and decides that she wants to keep the baby, effectively binding she and Ben together for life. 

Back in the day — before the word “shmshmortion” would even be mentioned in a movie like this — it was often a man’s values that saved a woman from herself, but “Knocked Up” flips the script and tilts the playing field in the other direction while still giving audiences plenty of time to laugh at the stunted hilarity of Rogen, Jonah Hill, Jason Segel, Jay Baruchel, and Martin Starr all living together in a massive puff of their own pot smoke. The result is a rom-com that feels traditional and progressive in equal measure, and also happens to offer the movies’ most honest template for the experience that any two people might have during a pregnancy. —ZS

2. “The 40-Year-Old Virgin” (2005)

Indisputably one of the most influential films of the 21st century, Judd Apatow’s directorial debut ushered in the golden age of the bromantic-comedy, pivoting away from (and ruthlessly dismantling) the pussy hound masculinity of movies like “Road Trip” and “Wedding Crashers” and inviting the men of America to get in touch with their feelings.

Using the multiplexes to reach an audience that “Freaks and Geeks” never could, “The 40-Year-Old Virgin” anointed a new generation of comedy stars en masse: It introduced the world to the likes of Seth Rogen and Jonah Hill (the scene at the Ebay store belongs at the front of the Louvre), it cemented Steve Carrell as a leading man, and it allowed everyone from Elizabeth Banks to Paul Rudd to reassert control over their images and take their careers to hilarious new places. 

Even now that Apatow has become an empire unto himself, this good-natured story about a sexually stunted tech salesman and his moron co-workers is still one of the funniest things that he’s ever made. And even now that “The 40-Year-Old Virgin” has become the most ubiquitous thing on cable TV since “Ridiculousness” or that infernal Kars-4-Kids commercial, catching it on TBS for the 900th time never leaves you feeling like if you hear “Yah Mo B There” one more time you’re going to Yah Mo burn this place to the ground. Every set-up is bursting with the kind of dialogue that people will be quoting with their friends until the day they die (“Bag of sand?”), and every scene is packed with so much comedic dynamite that even the most basic shots of the main cast standing around their electronics store are primed to explode like Michael Bay setpieces.

Every generation gets a handful of comedies that manage to catch lightning in a bottle — “The 40-Year-Old Virgin” does that so consistently it convinced people that Apatow could control the weather. —DE

1. “Funny People” (2009)

A massive blank check of a movie that’s more precariously balanced on the border of adolescence and adulthood than anything Apatow has directed before or since, “Funny People” may not be his most likable film (it’s certainly not his most well-liked), but this brilliant and uncomfortably lived-in Adam Sandler vehicle about “dying” Hollywood mega-star George Simmons is the most heartfelt and unsparing of Apatow’s stories about men who self-infantilize for their own emotional safety.

If so much of Apatow’s work challenges men to figure out what’s really important to them, “Funny People” raises the stakes to a matter of life and death. When was the last time a multiplex comedy included a moment as heavy and harrowing as the moment in which George silently contemplates his own mortality while listening to Warren Zevon’s “Keep Me in Your Heart”?

The film’s showbiz commentary — and the vulnerable self-analysis that it inspires from its leading man — can be cuttingly hilarious (“Yo, teach… thanks”), but “Funny People” isn’t really a story about the value of artistic integrity so much as it’s a story about the value of everything else. This is the film that most fundamentally affirms the strict moral humanism of Apatow’s art, clarifying him as a no-holds-barred Frank Capra with a dirty mind, a good heart, and a hyper-referential love for pop culture.

The third act has received a lot of flack over the years for taking the film well beyond the two-hour mark and introducing new characters very late in the game, but the raw beauty of Apatow’s epic lives in the friction between the fantasy of what George wants and the reality of what comes with it. Happiness isn’t as easy as catching up with the one who got away. He can’t go back in time, he can’t get back with the girl who got away, and he can’t magically transform celebrity into love.

Apatow’s other movies argue that monogamy is the most reliable way to save men from themselves — this is the only one that denies its hero that option. Instead, “Funny People” leaves George sitting across a deli table from his schlubby former assistant (Seth Rogen), workshopping some of the kid’s new material, and realizing how much richer life can be when he lets other people in on the joke. —DE