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Comedy in the ’90s, Part 4: ‘American Pie,’ the Raunchy Culmination of a Decade of Family-Friendly Films

As kids in the ’90s grew up, so did the movies they watched—from ‘Home Alone’ to ‘Clueless.’ That maturation continued into 1999, the year that saw the release of one of the dirtiest, most successful comedies of the decade.

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 4 of Comedy in the ’90s, our six-part series documenting this decade-defining boom in all of its sophomoric glory.

Seann William Scott was perhaps the worst employee in Home Depot history. While working at a Los Angeles location in the late 1990s, the wannabe actor spent his shifts hiding in a crawl space where the surplus shower doors were stored. “I always said I was busy with a customer, which was actually more exhausting than if I had actually worked,” he says. “It makes it feel twice as long when you’re faking like you’re busy.”

During one particularly dull day, Scott decided to pass the time by reading a trade magazine. In it, there was an article about studios’ renewed interest in teen movies. A hot script mentioned in the story jumped out: Untitled Teenage Sex Comedy That Can Be Made for Under $10 Million That Most Readers Will Probably Hate But I Think You Will Love. “I didn’t have a title,” screenwriter Adam Herz says. “My manager was like, ‘I wish we could call it that.’ And I was like, ‘Let’s call it that.’ You spell it out for the studios.”

When the comedy was being cast, Scott sought out and landed an audition, though he still isn’t sure how anyone agreed to see him. After all, by then he was 20-something—going on middle age. “I always looked 50, man,” he says. “I looked 50 since I was in seventh grade.”

Without much hope of actually landing the part, Scott decided to slightly reshape what was on the page. “I’m like, ‘I’m gonna change some of the dialogue and take characteristics from all of my friends from Minnesota and try to make him the guy that you hate to love,’” the Twin Cities–area native says. The move paid off: casting director Joseph Middleton asked him to come back and read for codirectors Paul and Chris Weitz.

“Fuck, I don’t know how I’m gonna get out of Home Depot,” Scott recalls saying to himself. After appropriately readjusting his priorities, though, he skipped out on a shift to meet the Weitzes. After running through his lines once, the brothers asked him to do it again, but instructed him to tone down his assholishness. “Then I did it the exact same way: like an asshole,” Scott says. “And walked away like, ‘Well, I’m never getting that.’”

But a month later, Scott got a call from a fellow actor. “I read for that sex comedy thing,” Scott says the friend told him, “and the casting director said, ‘You do not look like a virgin in high school. You can maybe play this other guy, but we kind of got our guy for that.’ … Yeah, my buddy who auditioned for it, we were saying you’re gonna have a challenging time finding virgins. And they go, ‘Who’s your friend?’ And he goes, ‘His name is Seann Scott.’ And they go, ‘That’s our guy!’”

As soon as he got off the phone with his friend, Scott decided to quit his job at Home Depot. “I didn’t even get the part yet,” he says. “But I’m like, ‘Fuck, man, I’ve never even really acted before. If I get this job I don’t know what I’m doing and I gotta make my mark. I’ve gotta try to get myself in as much of this movie as possible.’ And I just kept looking at the script going, ‘Where can I find little things I can add so I can get more screen time.’”

It’s safe to say that he figured out how to make his presence felt: Scott’s character, Stifler, became an oft-quoted, oft-derided icon in the teen movie canon, a lovable but hateable, gross but somehow endearing lax bro who Scott would go on to play in three sequels. The defining role of his career, the mononymous Stifler (his first name is Steve) opened the door for Scott. But he’s just one of dozens of young stars whose careers took off in the ’90s because of the teen movie boom. “There couldn’t have been a better time, I think, for an actor in the late teens, early 20s to try to make it in Hollywood,” Scott says, “because obviously there were so many films geared towards that audience.”

Since then, that kind of big-screen comedy has largely disappeared. “At that time, it was awesome,” Scott says. “Because that’s all there really was.”

The teen comedy explosion of the late ’90s wasn’t a freak accident. It was the culmination of a decade’s worth of funny movies made for kids. A generation that grew up in the early part of the decade had been weaned on mostly innocuous but sometimes subtly subversive family films and the goofy work of Jim Carrey and Adam Sandler; harder-edged humor, as the four protagonists of the era’s biggest, raunchiest teen movie might put it, was the next step. “There were all these comedies that we loved but they were just silly,” Herz says. “They didn’t live in any sort of reality and they weren’t really targeted to any audience other than, ‘Do you like silly shit? Watch Adam Sandler act like a child.’”

Sandler’s juvenile sense of humor may have endured, but it also prompted a need for vastly different sensibilities. As those early ’90s kids grew up, so did their tastes, which then also broadened and split. In response, studios began to make youth-centric comedies that appealed to more than just teen boys (in fact, many aimed for the exact opposite audience), a widening of scope that resulted in a series of unlikely classics that were both hilarious and smart enough to transcend the often pejorative “teen movie” label.

By the end of the ’80s, the genre of Fast Times at Ridgemont High, Risky Business, Revenge of the Nerds, and Better Off Dead... had grown stale. Even filmmaker John Hughes, who had elevated the form with movies like The Breakfast Club, Pretty in Pink, and Ferris Bueller’s Day Off, was moving away from coming-of-age stories. In 1989, he directed Uncle Buck, starring John Candy as a warmhearted slob pressed into babysitting his brother’s children. One of those precocious elementary schoolers was Macaulay Culkin, and after Uncle Buck piled up $79.3 million at the box office against a budget of $15 million, 20th Century Fox rushed Hughes’s next script, another family comedy called Home Alone, into production. On the recommendation of Hughes, director Chris Columbus cast the 9-year-old Culkin.

In what basically turns into Straw Dogs–for-kids, mistakenly abandoned second-grader Kevin McCallister scarfs down junk food, becomes a crack shot with his brother’s BB gun, gets over his fear of his basement, and rigs his house with dangerous booby traps to protect himself from burglars. The film came out on November 16, 1990, and unfathomably pulled in $476.7 million worldwide. “It was a freak thing and it was driven by one concept: empowering little boys to protect the house and be OK in the dark,” says Home Alone cinematographer Julio Macat, who went on to shoot Ace Ventura: Pet Detective, The Nutty Professor, and Wedding Crashers, among many others. “Everybody in fuckin’ America and the world could relate.”

Home Alone was so huge that it led to a collective inferiority complex. Upset that their films were being crushed by the movie, whiny power brokers coined a new term in its honor. “It added a new verb to Hollywoodese: to be Home Aloned,” Academy Award–winning screenwriter William Goldman wrote in his 2001 essay collection, The Big Picture. “More than one executive said to me, ‘My picture did 40 but it would’ve done 50 if we hadn’t been Home Aloned.’”

Above all, Home Alone’s success underscored the fact that there was an appetite for family comedies—Teenage Mutant Ninja Turtles, Kindergarten Cop, and The Addams Family were also among the top-grossing films of 1990 and 1991. Though it was then at the start of an animation renaissance, Disney was also churning out kid-friendly live-action hits. In 1992, when it had the year’s box office champ with Aladdin, the company and its affiliates released Sister Act, the Honey, I Shrunk the Kids sequel Honey, I Blew Up the Kid, martial arts–infused Home Alone rip-off 3 Ninjas, and sports movie The Mighty Ducks.

Emilio Estevez in ‘The Mighty Ducks’
Walt Disney Studios Motion Pictures

In the late ’80s, Steven Brill wrote the Minnesota-set underdog hockey comedy on spec. He at first envisioned it as The Bad News Bears for the ’90s, but had to sand off some—though not all—of its rough edges. In the final cut, Emilio Estevez, who plays coach Gordon Bombay, is still forced to work with a pee-wee team as community service after a drunk driving arrest. And there are still mild masturbation jokes. “The original script for that was certainly darker,” says Brill, who went on to direct Heavyweights, a weight loss camp–set comedy that he cowrote with Judd Apatow. “More like Bad Santa. But Disney in that era of filmmaking sort of knocked it down a bit.”

For a light kids’ movie, The Mighty Ducks was oddly influential. It grossed $50.7 million against a $10 million budget and spawned two sequels, as well as a youth sports movie movement highlighted by The Sandlot, Rookie of the Year, Little Giants, and Little Big League, and bizarrely, an actual professional hockey club. “They’re calling an NHL team the Mighty Ducks,” says Brill, who in the mid-’90s sued Walt Disney Pictures for a cut of the profits generated by a sports franchise that wouldn’t have existed without him, “and they’re playing the New York Rangers.”

Paul Rudnick, like Brill, was trying to be transgressive when he penned his initial treatment about an undercover nun. He’d hoped to satirize earnest convent-set dramas like The Sound of Music and The Singing Nun. “My plan was for Sister Act to subvert this sort of prissy uplift,” he wrote in The New Yorker in 2009. “I wanted our heroine, Terri Van Cartier, to embody raunch, sex, and the unstoppable gospel of cheap showbiz. It would be pop versus Pope; and pop, in a barrage of sequins, wisecracks, and Marlboro Lights, would win. That’s how addled or innocent I was, because I actually believed that Disney would make a movie that tried to subvert the Catholic Church.”

Multiple rewrites turned Sister Act’s screenplay into something that was a little too much like the kind of story that Rudnick had set out to send up. He eventually quit the film and then asked to be credited as Joseph Howard, a pseudonym that Disney approved. “Even though it sounds like the name of someone who helped found the Mormon Church,” wrote Rudnick, who went on to pen Addams Family Values, a truly subversive sequel that features a scene in which Christina Ricci’s Wednesday Addams, while starring as Pocahontas in a summer camp play, improvises a coup against the colonists.

Originally written for Bette Midler, who dropped out and later regretted it, the lead role of Sister Act went to Whoopi Goldberg. Fresh off an Oscar-winning performance in Ghost, she decided to reshape the character in her own image, changing her name from Terri to Deloris and playing down her ability as a vocalist. “It was written for somebody who could sing,” Goldberg told Entertainment Weekly in 2017. “So the only thing I said was, ‘You know that that’s not really what I do, so she can’t be a great singer. She has to be, like, a one-hit wonder.’ And they were like, ‘Whatever you want to do, let’s have some fun.’ And the rest is kind of wonderful.” Bolstered by Goldberg’s comedic chops, Sister Act raked in $231.6 million globally. She earned a Golden Globe nomination, and the next year went on to reprise the role in the far-less-profitable Sister Act 2: Back in the Habit.

Whoopi Goldberg in ‘Sister Act 2: Back in the Habit’
Buena Vista Pictures/Courtesy

But in 1993, Goldberg wasn’t the only comedy icon to play a character in disguise in a family film. Directed by Chris Columbus, who had just made Home Alone 2, Mrs. Doubtfire starred Robin Williams as voice actor Daniel Hillard, whose divorce from his wife (Sally Field) leads him to concoct an alter ego of an elderly Scottish housekeeper named Euphegenia Doubtfire in order to spend more time with his children. (No one said the family comedies of the ’90s had true-to-life premises.)

With a lesser talent carrying the film, it could’ve been disastrously silly. But Mrs. Doubtfire was the perfect vehicle for Williams, who seemed to relish the chance to play an old lady. (Williams claimed to have jokingly visited a sex shop in full costume when the movie was shooting in San Francisco—after an amused cashier recognized him, however, he left without buying anything.) For kids growing up at the time, Mrs. Doubtfire was a go-to video store rental. “There’s a scene in that movie when he calls Sally Field, he pranks her as a bunch of really bad nannies,” says Broad City’s Paul W. Downs. “And I think my first foray into making people laugh was just imitating him doing those different voices.” Williams imbued Mrs. Doubtfire with both wildness and warmth, imparting lessons about the realities of divorce with a Trojan horse covered in shaving cream.

For his performance, Williams won a Golden Globe, while Mrs. Doubtfire dominated in theaters, grossing $441.3 million worldwide. In 1993, only Jurassic Park made more money at the box office.

Post–Mrs. Doubtfire, kids suddenly had more choices at the multiplex. The problem was that the vast majority of the comedies made for them were pure schlock. Young moviegoers were treated to junk like Blank Check (kid, played by Brian Bonsall from Family Ties, uses a computer to write himself a $1 million check), Monkey Trouble (kid, played by Thora Birch, acquires a pet capuchin that’s a skilled thief), and Getting Even With Dad (kid, played by Macaulay Culkin, reconciles with his ex-convict father). There were some massive family-friendly hits—live-action adaptations of The Flintstones, Casper, and Jumanji, and holiday comedy The Santa Clause were among the top-grossing films of the mid-’90s—but few true bright spots.

Soon, however, things began to change. As Jim Carrey, Adam Sandler, and Chris Farley were becoming household names, the audience for PG films was growing into PG-13 and R-rated comedies. In 1994, rapper and actor Ice Cube and record producer DJ Pooh cowrote a script based on experiences from their childhoods in South Central L.A. Dramas like Boyz n the Hood—Ice Cube’s first movie role—and Menace II Society realistically portrayed aspects of their neighborhood, but they hadn’t told the whole story. “All of them show the horrors of living where we lived,” Ice Cube told Rolling Stone in 2015. “But growing up in South Central, we feel like, damn, we was having fun. Wait, what did we miss? We know it had its bad moments, but for the most part, there’s no place I would rather grow up.”

Ice Cube and Chris Tucker in ‘Friday’
New Line Cinema

Ice Cube and DJ Pooh’s screenplay for the film that became Friday follows buddies Craig and Smokey, who spend a typical Friday in the hood while also scrounging together $200 to pay back drug dealer Big Worm. In Complex’s oral history of the movie, Ice Cube explained that he didn’t expect Hollywood to understand a comedy told from the perspective of two young black men, but knowing that New Line Cinema had made House Party, he and his film’s producers approached the studio and eventually struck a deal. F. Gary Gray, who had collaborated with Ice Cube on the “It Was a Good Day” video, would direct. “He was a talented director from the hood,” Ice Cube told Complex. “You didn’t have to teach him these little nuances that were in the movie, like Big Worm’s rollers and shit. He knew all the hood flavor that needed to be in the movie.”

Ice Cube starred alongside comedian/future Rush Hour star Chris Tucker, who got the part after Cube and DJ Pooh saw him perform on Def Comedy Jam. Ice Cube’s goal was to make a quotable “hood classic,” and that’s what he did. (See: “Bye, Felicia.”) Friday, which had a budget of $3.5 million, hit theaters on April 26, 1995, and pulled in $28.2 million at the box office.

Friday proved that young comedy fans were into more than the homogenous slate of funny movies that were produced for them, that there was space for films that didn’t solely focus on suburban white boys. And three months after Ice Cube’s film entered the teen comedy pantheon, another unique filmmaker released an entry of her own.

In the early ’90s, Amy Heckerling was coming off making Look Who’s Talking and Look Who’s Talking Too. Those may not have been on the cutting edge of comedy, but a decade before, she had directed one of the rawest teen movies of all time: Fast Times at Ridgemont High. Based on screenwriter Cameron Crowe’s nonfiction book of the same name, the 1982 movie featured plenty of laughs, but in addition to highlighting the weed-fueled exploits of surfer Jeff Spicoli and Linda walking in on Brad masturbating in the bathroom, Fast Times offered an honest, sometimes downright disturbing look at how inexperienced teens navigate relationships and sex.

In the early ’90s, Heckerling went back to high school, this time with a potential television series called No Worries. Her idea was to make a modern, Beverly Hills–set version of the Jane Austen novel Emma, with touches of Howard Hawks’s Gentlemen Prefer Blondes. “Those characters: what I gravitated to was how positive they could be,” Heckerling told journalist Jen Chaney in 2015. When Heckerling’s agent, Ken Stovitz, read the show’s pilot, though, he envisioned it as a movie. And that’s what the project became.

Heckerling’s script, retitled Clueless, brimmed with dialogue that was seemingly lifted directly from the halls of Beverly Hills High School. Quips like “Uh, as if!,” “You are a snob and a half,” and “She’s a full-on Monet,” not only stood out, but became part of the culture as a whole. “It had enormous energy in the language,” producer Scott Rudin, whose many credits include No Country for Old Men, The Social Network, School of Rock, and Zoolander, said in a 2008 NPR interview. “It felt completely invented in the most pleasurable way.”

While writing Clueless, Heckerling noticed teenage actress Alicia Silverstone in the video for Aerosmith’s “Cryin,’” particularly the part at the end, when Silverstone bungee jumps off a bridge and flips off the camera. From that moment on, Heckerling saw Silverstone as Cher, her movie’s lead. “I’m always on the treadmill watching videos starring millions of supposedly hot girls,” Heckerling told Silverstone in a 2012 dual interview with Bullett. “But I responded to you. … I had a vague notion in my head of Cher as a pretty, sweet blonde, who, in spite of being the American ideal, people still really like. You had that Marilyn Monroe thing.”

Alicia Silverstone and Stacey Dash in ‘Clueless’
Paramount Pictures

According to As If!, Chaney’s oral history of Clueless, several studios, including Fox, which initially owned its rights, passed on the film. The relatively tight budget of $13 million and the prospect of Silverstone starring wasn’t enough to entice anyone. “We got rejected so many times it was a joke,” Stovitz told Chaney. But the movie was saved by Rudin, who got a look at the script after Heckerling’s agent sent it to him out of desperation. With Rudin on board, Paramount agreed to make the movie.

After a casting process that sounds, in hindsight, apocryphal—Reese Witherspoon, Gwyneth Paltrow, Angelina Jolie, Tiffani Thiessen, and Keri Russell were all reportedly at least discussed as the potential lead; Zach Braff, Ben Affleck, Dave Chappelle, and Terrence Howard were also in talks to be in the movie—Silverstone got the part of Cher Horowitz. She was joined by, among others, Stacey Dash as her best friend Dionne, Paul Rudd as her stepbrother Josh, Brittany Murphy as new student Tai, Donald Faison as Dionne’s boyfriend Murray, and Justin Walker as Cher’s love-interest-but-actually-gay-classmate Christian.

Everything about Silverstone’s performance is charming: Her eagerness, her vulnerability, even the way she mispronounces Spartacus as “Sparaticus.” Real-life teens quoted her and wanted to wear what she wore. With Cher, Heckerling had created a teenage girl who other teenage girls could latch on to—and that wide appeal bore out at the box office. Released on July 19, 1995, Clueless made $56.6 million against a $12-13 million budget.

“The movie just had an outrageous sparkle to it,” says writer Kirsten “Kiwi” Smith. After seeing Clueless, Smith and her writing partner Karen McCullah set out to find a literary classic to adapt into a high school–set film. “We were on the hunt for IP before we knew it was called IP,” says Smith, who also remembers being inspired by Baz Luhrmann’s 1996 version of Romeo and Juliet, which starred Leonardo DiCaprio and Claire Danes. “And we were just reading CliffsNotes, which I don’t even know if they still exist. We were going to libraries and researching myths and fairy tales.” Then one night in a bar, a friend asked, “‘What if you did Taming of the Shrew and switch the genders?’” Smith recalls. “We were like, ‘Oh yeah, that’s great!’”

Soon McCullah and Smith started writing a script. Six months after they finished the screenplay, Disney optioned it. The company, forever eager to capitalize on a money-making trend, was jumping on teen movie scripts. It also purchased the rights to another one, Heather Thomas’s School Slut, which Entertainment Weekly called “a ’70s-era dark comedy described as a cross between Welcome to the Dollhouse and Heathers.” (It did not later become Easy A.)

Perhaps unsurprisingly, Disney chose to green-light Smith and McCullah’s less profanely titled comedy. And on March 31, 1999, about two months after Pygmalion-based teenage rom-com She’s All That came out, 10 Things I Hate About You hit theaters. Featuring Joseph Gordon-Levitt, Julia Stiles, and Heath Ledger in his first American movie role, the Seattle high school–set comedy grossed $53.5 million against a $30 million budget. Like Clueless, it became a classic teen movie. “Suddenly,” Smith says, “that genre was up on its feet.”

The movie that most influenced the biggest teen comedy of the ’90s, however, wasn’t actually one itself. Directed by ’80s horror king Wes Craven and written by eventual Dawson’s Creek creator Kevin Williamson, Scream was a shockingly popular movie, making $173 million at the box office at a time when slasher flicks had all but vanished. But despite the fact that Scream was an often brutally violent, meta-whodunit horror movie, the thing about it that studios latched on to most is who it was about, and who flocked to see it: teenagers.

Adam Herz, then an aspiring screenwriter, remembers coming across a USA Today article about how Scream signaled the triumphant return of teen films. As motivation, he cut the story out of the newspaper and taped it on one of the walls of his apartment. “Well shit, now I gotta get my movie written,” Herz recalls thinking to himself, “because someone else is gonna beat me to it.”

Herz’s idea was to resurrect the teen sex comedy, a genre that appeared to have died back in the ’80s. As a student at the University of Michigan in the early ’90s, he’d written three papers on Porky’s, Bob Clark’s crass ’50s-set 1981 film about sex-obessed high school boys. “Just as kind of an F-you to the whole film studies thing,” Herz says. To prepare for writing his movie, he watched comedies like Revenge of the Nerds and Fast Times at Ridgemont High.

“I literally went through all my favorites,” Herz says. “I went through Porky’s and I did a beat sheet. Like, I just broke it down on an old VHS tape, pausing it and notating each scene. What’s it about? How do these movies work?” While taking note of the conventions of the genre, he also vowed to make his film more warmhearted and less sexist than teen movies of the past. (Today, Herz admits that he didn’t completely achieve that goal.)

The screenplay, about four clueless high school seniors’ quest to lose their virginities, featured a scene where a teenager humps a baked good; Stifler mistakenly drinks a semen-tainted beer; a nerdy band camp girl is revealed to be a sexual dynamo; and the acronym “MILF” is formally introduced into the lexicon. It was eventually renamed American Pie, after its, well, key object. Yet all that raunchiness doesn’t undermine the story’s obvious message: Sex isn’t simply something to be attained. Herz’s main characters, despite their misguided attempts to get laid, are, deep down, very sweet. “Why would you want to write something about people being mean?” he says.

Eugene Levy and Jason Biggs in ‘American Pie’

In the heat of the teen comedy renaissance, Herz’s script sparked a bidding war. Universal reportedly bought it in 1998, the year that PG-13 teen ensemble comedy Can’t Hardly Wait came out, for between $650,000 and $750,000, and brothers Chris and Paul Weitz, who had cowritten the animated film Antz, were tapped to direct. “We went in thinking that we weren’t going to get the job, so we went in and spoke very plainly about what would help the script become a good movie,” Chris says. “And we were as surprised as everybody else when we got the gig because we had never directed a frame of film before.”

During casting, Herz recalls the Weitzes asking him to pull out his high school yearbooks to show them some of his classmates who inspired the movie’s characters. At the time, the directors had just seen a tape of young actor Jason Biggs reading for one of the lead roles. “They were like, ‘I think we found him,’” Herz says. “I remember one of my first thoughts was, ‘He kind of looks like my buddy Jim. And he kind of looks like me.’ I’m like, ‘Oh my God, what am I saying about myself? Do they think I’m a pie fucker?’”

Biggs ended up as awkward but kind Jim, while Thomas Ian Nicholas was cast as earnest Kevin, Chris Klein as jock Oz, and Eddie Kaye Thomas as insecure intellectual Finch. Natasha Lyonne (the wise-beyond-her-years sex expert Jessica), Seann William Scott (endearing dickhead Stifler), Alyson Hannigan (adventerous flutist Michelle), Jennifer Coolidge (Stifler’s mom), and John Cho (MILF guy) were cast as scene-stealing secondary characters. “There was a Jonathan Taylor Thomas kind of situation for us,” Chris Weitz says. “That was the one sort of person that the studio was kind of taking a run at. Fortunately for us, not because of anything wrong with him … he wasn’t interested in the slightest.”

And after nearly turning it down, comedy great Eugene Levy accepted the part of Jim’s father. In the original script, Chris Weitz says, the character was “much more of a red-meat, All-American dad guy. I think Eugene thought, very smartly, that it would be interesting to take him to a kind of neurotic, suffering, overprotective, overinvolved father.”

Looking back on making American Pie, Chris Weitz feels fortunate that at the time Universal had two big-budget films in the works—Meet Joe Black and Babe: Pig in the City—because that meant the studio left their $10 million comedy alone. “We felt a tremendous sense of freedom,” Chris Weitz says. “We would sort of come up with gags on the fly. I often say that the funniest line in the movie, Michelle saying to Jim, ‘Say my name, bitch!’ was basically Alyson Hannigan ad-libbing.”

First assistant director J.B. Rogers says that his biggest contribution to the movie happened during the filming of its key scene. Originally, the audience wasn’t actually going to see Jim and the pie in action. The A.D. recalls convincing the Weitzes to go for it. “I’m like, ‘Dudes, we got a pie, we got Jason Biggs right here, why don’t we just shoot him fucking the pie?’” Rogers remembers. “And they’re like, ‘Do you think we can do that?’ I’m like, ‘Yeah, we can do that! Let’s just do it.’” And so they did, basically ensuring what will be in the first line of Biggs’s obituary.

In July 1998, as the filming of American Pie was about to start, some of its cast and crew attended the premiere of the Farrelly brothers opus There’s Something About Mary. (The two films shared a first A.D. in Rogers.) When Herz saw the movie’s outrageous “hair gel” gag, he remembers panicking and running up to Rogers and a few other American Pie producers after the movie. “I’m like, ‘Does this hurt us? Are we gonna seem like we ripped it off?’” Herz says he openly wondered. “‘Because they had a cum joke and we have a cum joke?’ And they’re like, ‘No.’”

They were right. American Pie, which was released on July 9, 1999, grossed $235.5 million at the box office. Teenagers had to see it multiple times to catch all the jokes—the laughter was so loud that it drowned out half the dialogue. The only R-rated comedies of the decade to make more money were Pretty Woman, Jerry Maguire, and There’s Something About Mary.

On opening night, Herz remembers riding around L.A. in a party bus to pop into theaters around the city. “You just quietly walk in the back of the theater and you watch the audience,” he says. “And the reward for comedy is the laughter. So that was super, super cool.”

For the Weitz brothers, their directorial debut couldn’t have gone any better. But that made moving on from it challenging. “Everybody thought we were smart,” says Chris Weitz, who with his brother codirected About a Boy (2002) before moving away from comedy; Paul’s credits include Little Fockers (2010) and Admission (2013). “That’s what happens when your movie does well. Everybody thinks you have some sort of magic pixie dust. So it’s a rare state of affairs in my life. We sort of thought, ‘Well this is how movies work.’ You make it and it makes $100 million and everybody thinks you’re great. And it’s high fives all around. Of course, that’s pretty much the best reception we’ve ever had for a movie. I wish that I had turned it into a life of debauchery by partying. But I didn’t have the sense to do that.”

For a generation of kids, American Pie was the end of a strange journey. They began the ’90s rooting for a little boy who had to defend his house and ended it by watching a high school senior have sex with an apple pie. As the pop-punk band who made a cameo in the movie so aptly put it, I guess this is growing up.

Naturally, after the unbelievable success of American Pie, many inferior imitators, including a series of officially licensed straight-to-video spinoffs, followed. Teen movies, which had seemingly gone extinct, had come back to life. They became so rapidly and so exhaustingly ubiquitous that in 2001, the genre was spoofed—and in a lot of ways, killed—by the hit Not Another Teen Movie. (Playing the archetypal jock was a true comic genius: Chris Evans.)

For Seann William Scott, who says that he got paid less than $10,000 to play Stifler, being part of the American Pie phenomenon was surreal. At the film’s premiere, he couldn’t believe that teenagers were asking for his autograph. “We were walking down Universal CityWalk to the theater and I walked by this place I used to work at, Scientific Revolution, where I used to sell glow-in-the-dark stars and Bill Nye the Science Guy puzzles, a year and a half before,” he says. “I’m like, ‘Holy fuck.’”

Not long after the movie came out, Scott was offered a part in director Todd Phillips’s comedy Road Trip. “I remember thinking, ‘God, this character’s really similar to Stifler,’” Scott says. “And I was like, ‘Who gives a shit?’ These characters are so much fuckin’ fun. I’d rather be the guy who says outlandish shit than the boring guy.”

It was a moment made for young actors like Scott. But it was as fleeting as it was fervent. While he’d permanently outgrown his job at Home Depot, his movie career was never hotter than it was in the post–American Pie years. Relatively soon after that, the supernova that had been growing for a full decade exploded into a black hole.

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