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Comedy in the ’90s, Part 6: Judd Apatow and the Decade That Followed

After a decade of glory for the genre, one man—flanked by a cadre of immature but well-meaning apostles—rose above the rest as blockbuster comedy made one last gasp

Dan Evans

Nearly 30 years ago, a handful of smart people set out with one mission: to make some silly movies. What followed was a true golden age of Hollywood comedy that saw the arrival of megastars still with us today, a commercial explosion, and then, an eventual splintering that changed the genre forever. Welcome to Part 6 of Comedy in the ’90s, our six-part series documenting this decade-defining boom in all of its sophomoric glory.

In the summer of 2003, Judd Apatow was itching to direct his first movie. The then-35-year-old filmmaker had spent the 1990s working with some of the industry’s funniest people on their passion projects. But the movies and television shows that he had created himself, while often well received by critics and a small number of passionate fans, had never risen above cult status. Apatow had a vision of a studio comedy that was a pastiche of his many influences: “Fun, big, broad comedy and set pieces, the types that I had seen Jim Carrey do in movies,” he says, combined with “a sensibility that’s grounded and human like you would see in a movie like Say Anything..., which Cameron Crowe made. Or Fast Times at Ridgemont High or Diner.” The problem was he kept getting turned down. “I couldn’t convince anybody to make the movies I wanted to make.”

Then, as a producer on Anchorman: The Legend of Ron Burgundy, Apatow found himself laughing at an actor who at the time was better known for his work as a Daily Show correspondent than for his various big-screen roles. In the farcical 1970s period piece, he played Brick Tamland, a meteorologist with the intellectual capacity of a lamp. His name was Steve Carell, and each of his improvisation-heavy takes was funnier than the last.

“He had been murdering every day,” says Apatow, who had something of a revelation on set. “I realized that maybe it would be better to find a new person because it would be fun to try to figure out how they worked as a lead,” he says. “But also they’re available! And they’re excited to do it. They’re not burned out.” He asked Carell, a Second City alum, for some ideas; one of his suggestions was a film about a kindhearted but stunted middle-aged man who had never had sex.

“I instantly knew that I related to the character that he was pitching me,” Apatow says. “I understood how to develop it. So we sat down and started writing. And even though it was a very silly movie, I still tried to write from a very personal place about my own insecurities and problems in the dating world.”

The script was built on a foundation of real-life experiences, a variety of comedic styles, and a performer who was finally getting a hold of a project that harnessed his unique abilities. Apatow’s collaboration with Carell was a starting point and a crystallization of a strategy: to recognize the offbeat talent in underused actors and help them make funny and emotionally resonant films. With the assistance of a profoundly talented group of disciples, Apatow spent the early part of the century going on an unprecedented comedic run. From 2005 through 2015, he wrote, directed, or produced 12 movies—including Superbad, Knocked Up, and Step Brothers—that made at least $100 million. Even a handful of his bombs became cult classics.

Apatow became a coach for whom everyone in comedy wanted to play. When asked what it was like being on his team in those days, Seth Rogen laughs his staccato laugh, and says, “It was like I had been training my whole life and then I was finally put in the game. I look back now and I’m amazed at how little I even thought about how all these movies were doing so well. … It felt just like how it should be at the time. Yeah of course. That’s just what happens. Then I very much learned that that’s not what just happens.”

“It felt like some version of a movement,” says actor and filmmaker Jay Baruchel, whose professional relationship with Apatow dates back to 2001. “There was a sort of unity of intent. We all kind of knew ‘We all want to do something good that makes us laugh. We all want to do something that we find funny. And we all enjoy each other’s company.’”

In the decade following the ’90s, the Apatow movement became a defining one for the world of comedy, launching those who were lucky enough to gain admittance and captivating all the rest. “It’s a weird thing to have a great deal of your conversations about a job you’re doing be met with envy from the people you’re talking about it with,” Baruchel says. “And every actor’s envious of every actor that’s working when they’re not. Actors are envious as a rule. But I got to have my cake and eat it too. Not only was I getting to work, I was getting to work on something good.” Consider: In 2009, longtime Apatow collaborator Jason Segel joined Maroon 5 on stage and sang a jokey love song. The chorus was his phone number. “I thought it would be some grand comedy experiment, where I’d save all these voicemails from people propositioning me,” he later told GQ. “And 80 percent of the messages were dudes saying, ‘Could you give my script to Judd Apatow?’”

But it’s also important to note, in hindsight, how concentrated of a moment the Apatow Era was; how bittersweet the ascent now seems. As Apatow was making hit after hit, the genre that he adored began to fall off a financial cliff. Only a decade removed is it possible to now see: His rise is the story of blockbuster comedy’s last stand.

Apatow’s obsession with comedy began early on. Soon after the Long Island–raised teenager’s parents divorced in the mid-’80s, he began seeking out the stand-ups whose acts helped him make sense of things. With the help of his mother, who worked at a local comedy club, he interviewed idols like Garry Shandling and Jerry Seinfeld for Syosset High School’s radio station. As a University of Southern California undergrad, he performed at the Hollywood Improv, where he met Adam Sandler; after Apatow dropped out of college, they became roommates. Hanging out with the SNL-bound Sandler daily, Apatow realized that he wasn’t meant for stand-up stardom. But he was funny and ambitious, and that led him to writing jokes for another one of his heroes, Shandling, and producing comedy specials for Roseanne and Jim Carrey.

Then, while waiting in line to get into Elvis Costello’s MTV Unplugged taping, Apatow met Ben Stiller. They had both heard that HBO was looking for a sketch show, and after talking, agreed to develop one together. The cable channel bought the series then sold it to Fox. In 1992, The Ben Stiller Show, a laugh-track-free sketch series showcasing Stiller, Bob Odenkirk, Janeane Garofalo, and Andy Dick, premiered. To Apatow, it was a lucky break. “I had never really done anything which would have earned me the right to do that,” he says. “At that time I had written some HBO specials and done some mediocre stand-up.” Stiller, who by the end of the decade became a movie star, was a profound influence on Apatow. “He was a genius at improvisation,” Apatow says. “He shot a lot of [alternate takes]. He really felt that comedy could be much more cinematic.” But after only 13 episodes, Fox canceled the program.

From there, Apatow worked on two series at once: Shandling’s late-night-TV satire The Larry Sanders Show and The Critic, an animated sitcom cocreated by peak-Simpsons showrunners Al Jean and Mike Reiss and executive produced by comedy guru James L. Brooks. “I feel like what I do is a combination of what I learned on those two shows,” Apatow says. “I was learning about very grounded emotional comedy. I was also learning about more imaginative, broader comedy.”

In the mid-’90s, Apatow started writing movies. His first was the PG-rated Heavyweights. “It’s a throwback to movies I grew up with like Meatballs, and yet Ben Stiller at the center is this demented owner of a summer camp for overweight kids,” Apatow says of the 1995 comedy, which was directed by Steven Brill and also featured a young Kenan Thompson. “We tried to make a movie that was hard funny but with a lot of heart.” The next year marked the release of three comedies that he contributed to, sports caper flick Celtic Pride, Sandler’s goon-turned-golfer comedy Happy Gilmore, and Stiller and Carrey’s bleak The Cable Guy.

The mostly impersonal movies that Apatow wrote early in his career failed to make a big splash, but they did provide him a front-row seat to the ’90s comedy boom. He also cites iconic films of the era that he didn’t work on—like Kevin Smith’s Clerks, Todd Solondz’s Welcome to the Dollhouse, Nicole Holofcener’s Walking and Talking, and Jon Favreau and Doug Liman’s Swingers—as major influences. “Judd is a fucking zeitgeist in corporeal human form,” Baruchel says. “He was there for all of it, 100 percent.”

By the time The Larry Sanders Show wrapped for good in 1998, Apatow had begun to figure out that the comedy he was drawn to was mined from real life. He enjoyed high-concept humor, but what fulfilled him most were personal stories. “I was mentored by Garry Shandling,” he says. “What I saw him do was take his own unique personality and worldview and turn it into characters like Larry Sanders and his version of himself on his Garry Shandling Show.”

After signing a development deal with DreamWorks, Apatow naturally jumped on his friend Paul Feig’s pitch: a show inspired by his often tortuous suburban Detroit childhood. NBC picked up the series, which had a legendarily talented cast, including Seth Rogen, James Franco, Jason Segel, Busy Philipps, Linda Cardellini, John Francis Daley, Martin Starr, and Samm Levine. When it premiered in 1999, the 1980-set Freaks and Geeks wasn’t like a typical network TV show. It starred actors who looked and acted like real teenagers. And it was full of simultaneously excruciating and funny moments ripped directly from the writers’ lives. “I think that’s where all the comedy in life is,” Feig, the hourlong dramedy’s creator and Apatow’s co-executive producer, once told me. “It’s cathartic remembering that stuff.”

In one painfully hilarious scene, as the audience hears “I’m One” by the Who, Starr’s character Bill Haverchuck makes a grilled cheese sandwich, grabs a hunk of Entenmann’s chocolate cake, sits down in his living room alone, and laughs himself silly while watching Shandling perform on The Dinah Shore Show. It’s exactly what Apatow used to do after school.

Freaks and Geeks has come to be recognized as one of the defining shows that led to the TV boom of the 21st century, but when it aired, ratings were low. “Television—and entertainment in general—is fantasy fulfillment,” Feig has said. “People, in general, don’t want to go through a bad experience, even if it’s done in a funny way.”

Unsurprisingly, after one season, NBC canceled the series. The network’s lack of faith was crushing for Apatow. “His joke is that everything he’s done since has been a reaction to Freaks and Geeks getting canceled,” says Jake Kasdan, who directed five episodes of the show. But while making Freaks and Geeks, Apatow succeeded in passing along his philosophy to his young charges. “I saw Jim Carrey work with Tom Shadyac to rewrite Ace Ventura and it made me realize that the only way to break through was to write,” he says. “Jim Carrey was so odd that there were no movies laying around that were perfect for him and he created this incredible career by doing this revision on Ace Ventura and tailoring it for himself. And then I saw Adam Sandler do that with Billy Madison. And all of my friends started writing themselves a career. So when we did Freaks and Geeks, that’s what I said to everybody.”

After Freaks and Geeks, Apatow created Undeclared, a half-hour college sitcom with yet another loaded cast featuring Rogen, Baruchel, Segel, and Charlie Hunnam. (At various points, Amy Poehler, Kevin Hart, Jenna Fischer, Will Ferrell, Ben Stiller, and Sandler all appeared.) Premiering in 2001, the series was more purely comedic than its predecessor. It also was ahead of its time in that it unabashedly riffed on modern pop culture: The show referenced things like the computer game Snood and D’Angelo’s provocative video for “(Untitled) How Does It Feel.” “We were allowed to make bits out of minutiae, out of wallpaper that nobody else found interesting,” Baruchel says. “And that just became what everybody did.”

But once again, the network wasn’t happy with the show’s ratings, and after only one season, Fox canceled Undeclared. However, the short-lived series exposed its cast and writers to a style of comedy—conversational, self-deprecating, full of pop culture references—that would soon become standard.

“On set that year, we knew we were at kind of the cool kids’ table,” Baruchel says. “And not the cool kids as in the popular kids. The cool kids who were usually druggies or into music. We really were incredibly elitist. We really thought we were doing something special, uncommon, and just better.”

At first glance, comedy at the dawn of the new millennium looked a lot like comedy in the late ’90s. Jim Carrey, Adam Sandler, and Mike Myers were still drawing at the box office; Farrelly brothers movies were making piles of money; Wes Anderson was creating droll and highly stylized films; and the American Pie franchise had plenty of life left.

But even before the Apatow era, the genre was branching off in different directions. In 2000, following the first two Austin Powers, director Jay Roach enlisted newly minted comedy star Robert De Niro to torment Ben Stiller in the $330.4 million smash Meet the Parents. In 2001, the same year Stiller’s Zoolander came out, the guys from MTV sketch show The State released a little-seen but beloved absurdist overnight camp classic, Wet Hot American Summer. In 2002, Nia Vardalos’s family portrait My Big Fat Greek Wedding was shockingly the ninth-highest-grossing movie of the year. The next year, Todd Phillips and the Frat Pack, including Vince Vaughn, Luke Wilson, and Will Ferrell, joined forces on Animal House 2.0, a.k.a. Old School. That year also marked the premiere of Richard Linklater and Jack Black’s opus School of Rock. And in 2004, Tina Fey’s sharp Mean Girls instantly became one of the best teen comedies of all time.

It was a good time to make relatively cheap, funny films. “When you’re talking about the late ’90s and ’00s, there was just a lot of movies being made for between let’s say $15 million to $35 million,” says Kirsten “Kiwi” Smith, who cowrote the 2001 Reese Witherspoon vehicle Legally Blonde, which made $141.8 million against an $18 million budget. “And if they made between $50-100 million that was OK because we had a pretty clear financial rate of return with DVD and home video.”

Yet in a booming comedy economy, executives remained risk averse, particularly when it came to movies that were, well, downright weird. When Adam McKay and Will Ferrell were at Saturday Night Live together in the early 2000s, they had cowritten August Blowout, about a Ford salesman named Jeff Tanner. Ferrell has called the scriptGlengarry Glen Ross meets a car dealership.” Despite interest from their boss Lorne Michaels, the film never got made. Fortunately for McKay and Ferrell, director Paul Thomas Anderson, who had read the screenplay during a guest-writing stint on SNL, met with the duo. He urged them to write another movie and offered to try to shepherd it into production. That’s when they conceived Anchorman, which initially centered on what happens when a private jet carrying newsmen to a convention crashes in the mountains.

“It’s just the story of them surviving and trying to get off the mountainside,” Ferrell said on The Bill Simmons Podcast in 2017. “They clipped a cargo plane, and the cargo plane crashed as well, close to them, and it was carrying only boxes of orangutans and Chinese throwing stars. So throughout the movie we’re being stalked by orangutans who are killing, one by one, the team off with throwing stars.” It was, as Ferrell pointed out, “maybe a little too weird for Paul.”

“No one wanted to make that,” McKay told me in 2018. Once again, a McKay-Ferrell project foundered. But after Ferrell’s Old School ($87 million) and Elf ($220.9 million) cleaned up at the box office in 2003, DreamWorks Pictures decided to finance the Ron Burgundy story. By then the script had morphed into something different and at least slightly more shootable. (There is still a cameo-studded news team battle royale and a climactic sequence in which Ron’s dog Baxter saves him from being eaten by a bear.)

Overall, the movie did what Ferrell and McKay hoped it would: gleefully make fun of a specific kind of deeply sexist, irrationally confident egomaniac. That wild comedic approach, aimed at an increasingly disturbing post-9/11 world, became their trademark. “Ferrell and I always found mediocre white men hilarious,” McKay says. “Anchormen, politicians, middle managers, CEOs. This was before these very same mediocre white men led us into a worldwide financial collapse and the Iraq War. Then it became a much darker subject matter. Ferrell was always amazing at capturing that blank-eyed certainty and the ridiculous anger that would result when these characters were challenged even just a little bit.”

Anchorman: The Legend of Ron Burgundy (2004)

“It was a formative experience for me,” says Apatow, who was brought on as a producer at the suggestion of Jimmy Miller, the manager he shared with McKay. “I got to see how they created this comedic world. It had a very strong comedic style. There was a lot of politics underneath the surface of the silliness. The set was very happy. They work from a place of being in a great mood.” It was, he adds, “the best possible version of how you make a movie.”

Made for $26 million and released on July 9, 2004, Anchorman grossed $90 million globally and cemented Ferrell as a comedy superstar. As a result of the movie’s success, a door opened for Apatow. Later that year, Universal Pictures green-lit The 40-Year-Old Virgin.

In Apatow’s directorial debut, Carell was joined by Rogen, Paul Rudd, and Romany Malco, who play the title character’s much more sexually experienced but far less mature coworkers. Apatow stuffed the movie with the kind of filthy but character-driven comedy that he loved. “When we were doing The 40-Year-Old Virgin table read, we were saying, ‘Do you think he masturbates? Do we talk about if he masturbates?’” Apatow recalls. “And Garry Shandling said, ‘You should do a sequence where you see him prepare to masturbate.’”

There were set pieces, too. The hirsute Carell goes through a real chest waxing and in the final scene, the cast performs an elaborate version of “The Age of Aquarius.” There’s also no shortage of humanity. Carell’s Andy, who desperately wants a relationship with Catherine Keener’s Trish but is deathly afraid of telling her he’s a virgin, battles both his anxiety over his nonsexual history and his buddies’ ridiculously misguided thoughts about women. The comedy’s setting, a bustling big box electronics store in Los Angeles, was a purposely intricate backdrop for endless filthy banter. “I loved how dense the world was in that store and how many characters there were with their own unique thing going on,” McKay says. “I told Judd I could have hung out in that store for hours.”

Rogen remembers Apatow walking into the room laughing hysterically after having thought of the movie’s first gag: Andy waking up in the morning and walking into the bathroom with an erection that he has to push down in order to pee. “I remember [Apatow] saying in the first screening, ‘If they laugh at that joke then we’re fine,’” Rogen says. “And they did.”

On August 11, 2005, after it survived a brief production shutdown due to a spooked Universal executive’s claim that Carell’s character resembled a serial killer, The 40-Year-Old Virgin hit theaters. The hard-R-rated comedy cost $26 million and raked in $177.4 million worldwide.

His first time behind the camera, Apatow proved that the kind of movie that he was never given the chance to make—deeply personal, dialogue-heavy, and creatively profane—could appeal to a mass audience. There was equal appetite for real human moments that you never would have seen in an Ace Ventura or Austin Powers movie and for a level of daring R-rated humor that hadn’t graced studio comedy, like when Rogen’s character tells a story about seeing bestiality at a sex show in Tijuana. “Especially in the context of that time, it was a really dirty joke,” Rogen says. “In a theater full of people, it just destroyed. I remember thinking, ‘Yes, people want this. For better or for worse, they are ready.’”

Apatow next produced McKay, Ferrell, and John C. Reilly’s Talladega Nights: The Ballad of Ricky Bobby. The NASCAR comedy, Sacha Baron Cohen’s first live-action American film, came out the next summer and grossed $163 million. “It sort of put NASCAR on the map culturally,” Reilly says. “Even though we were really making fun of NASCAR for all these redneck clichés, people who love NASCAR were like, ‘Finally, a movie! Even if it’s making fun of us.’”

After three hits in three years, Hollywood finally began to see things Apatow’s way. “The studios opened up to the idea that maybe the audience doesn’t need an established star,” he says. “Maybe they just need somebody who’s great.”

Apatow responded to his new status as a power broker rather predictably: He immediately tried to make more movies. “As soon as they opened the floodgates, we were just like, ‘Go, go, go!’” Rogen says. “And it really was a manic act of just like finally making all this stuff that we’ve been wanting to make forever.” For Rogen, that meant Superbad, a movie that had been gestating even before Apatow spotted him in his native Vancouver at an open casting call for Freaks and Geeks. By then, Rogen was too old to star in the teen buddy comedy that he cowrote with his childhood friend Evan Goldberg. So Jonah Hill, who had a small role in The 40-Year-Old Virgin, stepped in and headlined with Michael Cera. Greg Mottola, who had worked on Undeclared, was hired to direct.

Around that time, Apatow also set out to direct Knocked Up, a film about a nebbishy, shiftless 20-something named Ben (played by Rogen) who gets a smart, attractive young woman named Alison (played by Katherine Heigl) pregnant during a one-night stand. Apatow’s wife, Leslie Mann, and Paul Rudd played Alison’s sister and brother-in-law, while Segel, Hill, Baruchel, and Starr appeared as Ben’s friends and roommates. “After Freaks and Geeks, there was a large group of people who I felt deserved to write and star in movies,” Apatow says. “Everybody was in front of me who I believed in. There was definitely a moment where we were all writing and producing and acting in all of these projects. And we were all helping each other.”

One thing that Rogen learned early on in his working relationship with Apatow was that the set didn’t have to be a deadly serious place. “It was very good that Judd was always like, ‘Don’t be too precious with any of this stuff. Try things,’” Rogen says, while noting that Apatow’s looseness also always had a purpose. “It’s easy to improvise. It’s hard to improvise in a way that adds to the story, that builds character, and that adds jokes that are actually funny because of the context of where they fall in the film.” What helped, Rogen thought, was that the vast majority of the performers he was working with were also writers. It makes sense that the pop-culture-infused scenes built around Ben and his friends riffing—like Baruchel singing the praises of Munich and the group making fun of Starr’s beard—are some of the movie’s best.

“I just want everything to be so thought through that the actors and actresses can play and feel their way around this moment and do what feels appropriate for them,” Apatow says. “A great example of this is the moment in Knocked Up when Katherine Heigl says that she’s pregnant. We ran that a bunch of times and we wrote all sorts of funny responses to her saying, ‘I’m pregnant.’ But in the moment, Seth just said in an improv, ‘Fuck off.’ Which is not something I would’ve written. But it’s perfect and hysterical.”

“Katherine was right there with him,” he adds. “So we wrote a lot of jokes and alts and we shot tons of them. But we also took time to let them be much looser with the material. And every once in a while something magical would happen. There was a moment where they’re having sex and Seth just improvised, ‘I’m sorry I’m sweating on you.’ I wouldn’t have thought of that.”

Knocked Up (2007)

Released in July and August 2007, respectively, Knocked Up ($219.1 million) and Superbad ($169.9 million) were massive hits. By that point, Variety had already dubbed Apatow the “new king of comedy.” In the next year alone, he had a hand in making five more films. “He has this strong producer’s impulse to kind of get things going,” says Kasdan, who directed the Apatow-produced 2007 fake music biopic Walk Hard. “So that there was always more around the corner. The part that was kind of unbelievable to see was how quickly he was, like, a famous person, you know? That was unusual.”

One was Segel’s passion project. After the studio had prevented Apatow from hiring the goofily lovable 6-foot-4 actor for The 40-Year-Old Virgin, the director gave him this advice: “You’re kind of a weird guy, I think you need to learn to write in order to get that perfect vehicle for yourself.” So that’s what he did. Directed by Nick Stoller, formerly a writer on Undeclared, Forgetting Sarah Marshall was the Hawaii-set character study of a man getting over a painful breakup. In typical Apatow movie fashion, the movie is full of dick jokes (and famously, one literal dick). In one scene, Hill’s resort waiter literally becomes aroused during a performance by Russell Brand’s rockstar Aldous Snow and quietly says, “I just went from six to midnight.” Hill came up with the joke while riding from the airport to the set with Rudd. “It’s pretty funny when someone repeats something [like that] back to you,” he says. Forgetting Sarah Marshall was endearingly odd—there’s a lot of crying in it for a comedy, and it ends with a Dracula musical starring puppets—but Apatow’s method of letting stars tailor movies to themselves continued to pay off. Released in April 2008, it grossed $105 million at the box office.

That June, Adam Sandler’s You Don’t Mess With the Zohan, which Apatow cowrote, was released and went on to make $199.9 million. Over the next two months, two more Apatow-produced $100 million movies hit theaters: McKay, Ferrell, and Reilly’s take on arrested development, Step Brothers; and indie director David Gordon Green’s stoner action comedy Pineapple Express, which starred Rogen (who cowrote it with Goldberg), James Franco, and Danny McBride. Also in 2008, Carell’s Get Smart remake pulled in $230.1 million and Stiller’s action movie send-up Tropic Thunder made $188.1 million. “You’ll never see a summer like that again,” says Peter Segal, who directed Get Smart. “All of those movies had big budgets. And all of them did over $100 million.”

But even though comedies were popular at cineplexes, the genre’s success wasn’t the biggest Hollywood story of 2008. That year, like every one since, belonged to superheroes. Box office champion The Dark Knight grossed over $1 billion. And Iron Man, the first entry in the Marvel Cinematic Universe, piled up $585 million worth of ticket sales. It was a sign of things to come.

In 2009, for the first time in years, Apatow’s reign as the king of comedy began to waver. That June, as he was putting the finishing touches on Funny People, The Hangover was released. Todd Phillips’s high-concept bro fest put a clever spin on the bachelor party movie and featured a likable cast, including Zach Galifianakis in his breakout role.

Noticeably, the crass blockbuster lacked the heart of Apatow’s recent hit comedies. In contrast, the Sandler and Rogen vehicle Funny People had almost too much heart. When it came out almost two months later, moviegoers and some critics didn’t appreciate the long-winded—its run time was 146 minutes—exploration of Sandler’s cynical, leukemia-stricken comedy star and his attempt to make amends after a career spent neglecting those close to him. Made for $75 million, by far the biggest budget of any film Apatow has directed, it made only $71.6 million at the box office. The Hangover, on the other hand, made $467.5 million and spawned a franchise. Funny People wasn’t an Ishtar-level failure, but it showed that Apatow wasn’t invincible, and that even though his style had just taken over, audiences—and more importantly, studios—were already looking for something different.

But as Apatow’s career as a director took an inevitable downturn, his diaspora began spreading out and developing their own styles of filmmaking. One-time Undeclared writer Rodney Rothman went on to codirect Spider-Man: Into the Spider-Verse; Freaks and Geeks alum John Francis Daley turned writer-director with credits that include Horrible Bosses and Spider-Man: Homecoming; Kasdan is now at the helm of the blockbuster franchise Jumanji; Stoller is still directing and producing comedies; Baruchel wrote a classic sports movie in Goon; Segel rebooted The Muppets and played David Foster Wallace in a biopic; Hill became an Academy Award–nominated actor and wrote and directed the drama Mid90s; Rogen started his own production company with Evan Goldberg, Point Grey Pictures, and continued to write and star in funny movies, including Observe and Report, Neighbors, and his directorial debut, This Is the End, the 2013 meta-apocalyptic comedy that brought the whole Apatow universe together for one final time.

As for Adam McKay, he’s built his own entertainment empire—and not coincidentally has moved away from traditional comedy. “This is very dark stuff and at the same time it’s beyond parody or satire,” he says. “The whole basis of comedy is breaking routine or consensual reality. Well how do you disrupt consensual reality when there is none?” The last two movies that he directed, The Big Short, about how the housing bubble led to the 2007–08 financial crisis, and Vice, about former vice president Dick Cheney, won Oscars.

Then there’s Kristen Wiig, who in 2011 busted up the Apatow boys club. The Saturday Night Live star, who had stolen all of her scenes in Knocked Up and Walk Hard, cowrote a script with Annie Mumolo about a single woman who feels directionless as her best friend is about to get married. “It was so exciting making a Kristen Wiig movie,” Apatow says. “And then when we were casting, it entered our consciousness more that it was an opportunity for so many of the great female performers who we loved.” Directed by Freaks and Geeks creator Paul Feig, Bridesmaids was carried by a spectacularly talented ensemble of women, including Maya Rudolph, Rose Byrne, Rebel Wilson, and Melissa McCarthy, who unleashed one of this century’s greatest cinematic performances. Before casting, Apatow wasn’t familiar with the Groundlings alum, who was then the star of the sitcom Mike & Molly. “When she walked in, that was the first time I had seen her in anything,” Apatow says. “So you can imagine how enjoyable that is. To have a comic force like that walk into the office to just start improvising off of a script.” Released in May 2011, the film made $288.4 million at the box office.

“Looking back, I’m just so proud of all of the work that everybody did,” Apatow says. “And I’m a fan of what everyone’s doing now. Even as our group is not as tightly knit as it was before, it seems like people keep pushing boundaries. Everyone’s doing daring work and following their hearts, and so it all continues.”

Bridesmaids (2011)

Amy Schumer’s 2015 film Trainwreck was the first film that Apatow directed but didn’t write. The movie represents much in the arc of Apatow, as well as in the evolution of big-screen comedy—it speaks to the creator’s eternal ethos of giving others a platform, but also to the changing way he was received, and the bar by which comedies were measured. The heartfelt, semi-autobiographical comedy was well reviewed and commercially successful, bringing in $140.8 million. But the criticism it faced for its portrayal of a party girl who can only find redemption through monogamy proved what was already apparent: that the full-throated approval of Apatow’s late-aughts comedy had waned; that he was no longer the primary voice in comedy. To this point, Trainwreck is the last Apatow movie to top the $100 million mark.

Though by then, comedies had already begun to lose their blockbuster potential. Since 2009, only two have cracked the yearly box office top 10: The Hangover and The Hangover Part II. There are several reasons for the genre’s slowdown. Apatow thinks it began during the 2007–08 writers’ strike, when studios stopped buying as many spec scripts as they used to. “There was a market for original ideas,” he says. “A lot of times they were sold as finished scripts, but they were also sold as pitched concepts. So every day you would read the trades and somebody sold a comedy screenplay, usually for a lot of money. I think the studios decided they didn’t want to invest that money in comedic movies.”

Elsewhere, the home video market, once a boon for studios that could package the millions of feet of film improv-friendly directors like Apatow and McKay shot into special edition DVDs, was collapsing. In 2011, four years after Netflix launched its streaming service, the Los Angeles Times reported that between 2006 and 2010 DVD revenue “for the average comedy” dropped 63 percent. Then came the rise of superhero movies, which ushered in an era of big-budget CGI extravaganzas that were—unlike comedies—practically guaranteed to appeal to global audiences. Funny movies with midrange budgets and midrange profits were no longer attractive. “Singles and doubles don’t really exist anymore,” Kiwi Smith says. “Once studios started spending upwards of $100 million to make movies, then all of a sudden the $100 million mark wasn’t really an accomplishment anymore. It sort of had to become a $200 million mark to really become a profitable franchise property.”

“It’s very rare that a hysterical movie isn’t a big movie that doesn’t make a lot of money,” Apatow says. “But it’s not where the industry wants to invest their money in the way they used to. They’re going to make that bet less often, because Avatar might make $2 billion.”

Seann William Scott, who got his start in comedy playing Stifler in American Pie, remembers a meeting with former Universal executive Scott Stuber. The two had worked together on Role Models, a 2008 buddy film that Scott costarred in alongside Paul Rudd. It cost $28 million to make and grossed $92.4 million. “He was like, ‘We could never make Role Models today,’” Scott says. “I was like, ‘Really?’” (Stuber did not respond to a request for comment.)

These days, Stuber is the head of original films at Netflix. At this point, it’s hard not to see streaming services as the biggest threat to theatrical comedies. With unlimited space for scripted content and seemingly infinite money, a digital platform can be awfully enticing to a creative person. Over the past few years, a raft of middling comedies that might have landed in theaters 10 or 20 years ago have ended up on various platforms. And in 2014, Adam Sandler, whose movies had grossed $3.9 billion at the box office by that point, signed a four-picture contract with Netflix. In 2017, he re-upped his deal. “What’ll it take for you to get off your couch and pay $18 to go to the ArcLight when you can sit at home and still watch movie stars?” Tommy Boy director Peter Segal wonders.

It would be incorrect, however, to say that streaming has been bad for comedy. Netflix has nearly single-handedly created a stand-up comedy boom. And streaming services have provided lucrative opportunities for writer-performers drawn to the kind of longform storytelling that films don’t provide. Comedy hasn’t died—its primary venue has simply changed from the big screen to the small screen. “Instead of making a movie, Aziz Ansari is going to do Master of None, and Ramy Youssef is going to do Ramy, and Aidy Bryant does Shrill,” Apatow says. Uncoincidentally, Apatow has spent the past few years shepherding TV shows like Girls, Love, and Crashing. McKay is an executive producer of Succession and is currently developing a miniseries about the ’80s Lakers.

“A lot of younger people don’t grow up idealizing movies in the same way that my generation did,” says the 37-year-old Rogen. “And so if you’re a young comedian now, your be-all end-all isn’t necessarily trying to have, like, Eddie Murphy or Jim Carrey’s career. It’s probably more like trying to have John Mulaney or Nick Kroll’s career. People who have found their unique comedic voices that are wildly popular and don’t rely on film studios.”

“Comedy, like everything else, is a constantly evolving thing,” says Daley, who codirected the 2018 comic thriller Game Night, which made $117.7 million against a $37 million budget. “And you can disguise comedies as other things. We were able to inject so much humor and fun into Spider-Man: Homecoming, which is not a comedy, but it also is. And so I think it forces filmmakers to think a little bit outside the box.” Over the past two years, Emily Gordon and Kumail Nanjiani’s The Big Sick—which Apatow produced—Malcolm D. Lee’s Girls Trip, Night School, and Kay Cannon’s Blockers all found success in theaters, though “success” for a comedy in the 2010s is an average intake of $74 million. The days of Dumb and Dumber’s $200 million hauls are long gone, and even relative comedy hits have become exceptions rather than expectations.

Marvel, DC, and Star Wars rule the box office now, and have taken over as Hollywood’s main source of profit. But there was a time in the ’90s and the early ’00s when comedy held that distinction. And when comedy was at its peak, there was no better theater experience. “Strangers are elbowing you because you’re laughing so hard,” says Ike Barinholtz. “It’s like you’re at a party together. It instantly puts you on the same page.”

In February 1994, Rogen saw Ace Ventura: Pet Detective on opening night. There was an unmistakable energy in the air; people were fighting over seats; it was a feeling that could have existed only during that period, when the biggest theaters in the biggest multiplexes were devoted to stars like Carrey, Myers, and Sandler. “It was one of the most packed, excited theaters I’ve been in in my life,” Rogen says. “With a half hour of therapy I could probably quickly uncover that that’s the dragon I’m chasing.”

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