American Pie followed the lives of a group of pals desperate to lose their virginities, with them getting up to no good as they went on their quest.
But their real life counterparts have had just as interesting lives, with failed attempts at a threesome, accidental boob flashes, stints in rehab and some legal troubles.
Tara Reid, who played Vicky, celebrates her 46th birthday today (November 8) and is probably best known in recent times for her stay in the Celebrity Big Brother house.
But what else have she and her co-stars been up to in the 22 years since the iconic movie was released?
Tara Reid / Vicky Lathum
Tara who played hot girl Vicky Lathum in the sex comedy, was the childhood sweetheart of Kevin Myers, after American Pie her acting career completely took off.
Soon after the launch of American Pie, Tara quickly became one of Hollywood's most vociferous party girls, alongside the likes of Paris Hilton.
Back in 2004, she suffered an iconic wardrobe malfunction while attending Diddy's 35th birthday party as she accidentally expose her left breast to the cameras.
She later said to FHM: "People act like it was the worst crime in the world. It was a mistake, you know!
"But you would think my boob had popped out and shot Gandhi! My hooters are under control.
"I’m taped up now, totally. I’m using double tape. Double double tape. My boobs are going nowhere again."
After facing tough press, for numerous drunken stumbles and various wardrobe malfunctions on many of her wild nights out, she eventually check in to rehab at Promises in Malibu in 2008.
When it seemed her career was at a dead end, suddenly the American beauty's life took a turn for the better, when the sci-fi movie Sharknado changed everything for her in 2013.
Jason Biggs / Jim Levenstein
Main character Jim Levenstein, who famously masturbated with a warm pie after being told it felt like "third base", went on to star in a number of romantic comedies after appearing in the film.
It wasn't until 2013 that his career took off once again after he landed to role of Larry Bloom in the Netflix hit Orange is the New Black.
More recently he starred in American buddy comedy Jay and Silent Bob reboot, reuniting Jason with director Kevin Smith who he had worked with previously in the past.
The actor, 36, also opened up about his failed attempt to have a threesome with his wife Jenny Mollen after she hired him a hooker as a birthday present.
Talking on The View in 2014, Jason said: "I didn’t have a good time in the end.
"It took three ladies over the course of three days. Let’s just say I didn’t complete the mission.
"She was actually on the bed, watching, eating a bag of chips, laughing, so as you can imagine, I wasn’t really performing to the best of my abilities.
"Also, said prostitute wasn’t engaging with my wife the way I hope she would, so it all kind of fell apart, and the rest is in the book."
Chris Klein / Chris "Oz" Ostreicher
Chris, who was better known as Oz in the film, was the ultimate 'kind jock' turned theatric, in his quest to land the girl of his dreams.
Prior to his role in American Pie, Chris had already made a name for himself after appearing in the movie Election.
His career seemed to be on the up, until things turned sour in 2005, when he was arrested for drunk driving and later joined an alcohol addiction program in 2010.
After a downward spiral, Chris managed to get things back on track accepting the villainous serial killer role Cicada in The Flash season 5.
Thomas Ian Nicholas / Kevin Myers
American Pie wasn't the making of Thomas, he already had a name for himself after landing roles in shows such as Who's the Boss, Baywatch and Married.. With Children.
Thomas also had a multitude of talents that were to be unveiled following his stint in the movie, when he went on to pursue his singing and writing career and even recorded a song for the American Reunion soundtrack.
In recent years, the hunk returned to his acting roots, appearing in the 2019 film Zeroville alongside the likes of Megan Fox, James Franco and Seth Rogen.
Eddie Kaye Thomas / Paul Finch
Eddie who was the most unlikely of the five-some to have sex before the end of the school year famously ended up in bed with Stifler's mum, in the film.
In 2001, he was cast as the lead role of Frederick 'Freddy', in Freddy Got Fingered and later appeared in Harold and Kumar Go To White Castle.
More recently, his career has stemmed around a number of successful US TV series, including Scorpion, Outmatched and Law and Order Special Victims unit.
Shannon Elizabeth / Nadia
Shannon became one of the hottest girls on the movie scene after she stripped off on the film American Pie, alongside Jim Levenstein who danced for her while the entire school watched the scandalous ordeal unravel via webcam.
Of course, the stunning brunette was snapped up by film bosses and later appeared in teen genre Scary Movie and That 70s Show.
Shannon decided to play a very different hand and astonishingly became a celebrity poker player, later competing in the World Series of Poker.
In more recent times, the sex symbol returned to her love of acting, taking to the stage again with her former American Pie co-star Jason Biggs, in the film Jay and Silent Bob reboot.
Jennifer Coolidge / Jeanine Stifler aka Stifler's mum
Stifler's mum was the ultimate teen MILF of her time, sparking up a whirlwind romance with her son's chum, Paul Finch, in the film.
After her success as Jeanie Stifler in the sequel films, she landed the iconic role as Paulette Bonafonté Parcelle in the Legally Blonde film series 2001–2003.
Her on screen career didn't end there – she starred in a number of comedy films such as A Cinderella Story, Two Broke Girls and The Emoji Movie.
Natasha Lyonne / Jessica
Natasha's character, Jessica was the experienced friend who provided childhood sweethearts Kevin and Vicky with all the sex advice they needed to get each other in the sack.
Her outspoken, no nonsense charm, earned her significant brownie points in the world of film and her acting career completely took off after her stint on American Pie.
However, she hit a rough patch in 2001 after battling drug addiction following an arrest for a DUI.
She also failed to appear for a hearing for charges from an alleged rampage in December 2003, where she reportedly was heard threatening to molest a neighbour's dog.
In 2005, she was admitted to intensive care of a hospital in New York for a collapsed lung and hepatitis C.
But she managed to get herself on the straight and narrow again and starred in films such as Slums of Beverly hills, Scary Movie 2, Girl Most Likely but her biggest claim to fame came later after she turned to TV.
The witty star landed herself a huge role on Netflix's Orange Is The New Black and Russian Doll which saw her swoop up a Primetime Emmy Award.
She has since become the star of Netflix show Russian Doll, a series about a game developer who repeatedly dies and relives the same night.
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