See What The Cast of ‘Never Been Kissed’ Looks Like 16 Years Later!

1
Drew Barrymore
Never Been Kissed, Drew Barrymore
20th Century Fox via Everett Collection/WENN
The same year Never Been Kissed came out, Barrymore began dating MTV comedian Tom Green, whom she married in July 2001. But, coming to her senses, she divorced him in December of the same year (after starring together in Charlie's Angels and Green's directorial debut, Freddy Got Fingered). Afterwards, she appeared in films like Donnie Darko, Riding in Cars with Boys, Confessions of a Dangerous Mind, Duplex, 50 First Dates, Fever Pitch, Music and Lyrics, He's Just Not That Into You, Whip It, Going The Distance, and Blended. In 2009, she starred in HBO's Grey Gardens, earning her an Emmy nomination and a Golden Globe award. In 2011, she began dating art consultant Will Kopelman, whom she married in 2012. They have two daughters, Olive (born in 2012), and Frankie (born 2014).
2
David Arquette
Never Been Kissed, David Arquette
20th Century Fox via Everett Collection/WENN
Arquette married his Scream co-star Courteney Cox in 1999, the same year Never Been Kissed came out. Together, they formed the production company Coquette, which produced Daisy Does AmericaDirt, and Cougar Town. Cox and Arquette have one child together, Coco Riley, who was born in 2004. The couple separated in 2011 after filming Scream 4 together, and Arquette began dating Entertainment Tonight correspondent Christina McLarty.  McLarty gave birth to the couple's son Charlie West Arquette in 2014 and the couple wed in April, 2015. Arquette's other film roles include See Spot Run, Eight Legged Freaks, The Adventures of Sharkboy and Lavagirl in 3-D, and in television series like Medium alongside his sister Patricia and Cougar Town alongside his ex-wife Courteney.
3
Michael Vartan
Never Been Kissed, Michael Vartan
20th Century Fox via Everett Collection/WENN
After playing Sam, the teacher you'd forever wish you had in high school, Vartan went on to star alongside Robin Williams in One Hour Photo and with Jennifer Lopez in Monster-In-Law. He also starred on the Jennifer Garner spy series Alias, as well as Jada Pinkett Smith's show Hawthorne. Most recently, he appeared on A&E's Bates Motel and USA's Satisfaction. In 2011, Vartan married Lauren Skaar, whom he met in a Whole Foods parking lot. The pair filed for divorce in 2014, proving the only thing you should leave the grocery store with is food.
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4
Leelee Sobieski
Never Been Kissed, Leelee Sobieski
20th Century Fox via Everett Collection/Splash News
The divine Sobieski, who played the coolest nerd in movie history in Never Been Kissed, was one of the few movie teenagers who was actually a teenager in real life. She was only 16 when she played the part of Aldys. She then went on to have roles in Stanley Kubrick's Eyes Wide Shut as well as the thriller Joy Ride. She also starred in a 1999 TV movie about Joan of Arc, for which she received Emmy and Golden Globe nominations, and she became the youngest actress to play Joan of Arc. In 2008, Sobieski married her first husband, Matthew Davis, who she divorced in 2009, when she began dating her current husband, fashion designer Adam Kimmel. She and Kimmel welcomed a daughter, Louisanna Ray, in 2009, and a son, Martin, in 2014.
5
Jessica Alba
Never Been Kissed, Jessica Alba
20th Century Fox via Everett Collection/Splash News
After her turn as snobby high school mean girl Kirsten, Alba landed her break-out role on James Cameron's Dark Angel, which earned her a Golden Globe nomination. She went on to star in Sin City and its sequel, Fantastic Four and its sequel, Good Luck Chuck, Honey, A.C.O.D., and Machete and its sequel. Alba married her husband, Cash Warren, in 2008 after meeting him while filming 2004's Fantastic Four. The couple have two daughters, Honor Marie (born in 2008) and Haven Garner (born in 2011). In 2012, Jessica Alba launched The Honest Company, a collection of toxin-free body care products, diapers, and household goods, which is currently valued at $1 billion, making Alba the "richest self-made woman in America."
6
Jordan Ladd
Never Been Kissed, Jordan Ladd
20th Century Fox via Everett Collection/WENN
Never Been Kissed was Ladd's first high profile acting gig, which she quickly followed with a series of horror films that helped land her a reputation as a scream queen: Cabin Fever, Club Dread, Death Proof, and Grace. While filming Never Been Kissed, Barrymore offered her a role in her adaptation of Charlie's Angels, which Ladd turned down. She'll appear next in 2015's Brentwood Strangler.
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7
Marley Shelton
Never Been Kissed, Marley Shelton
20th Century Fox via Everett Collection/Splash News
While most people likely remember Shelton from her iconic role as Wendy Peffercorn in The Sandlot, she's actually had quite the prolific acting career. After playing mean girl Kristin in Never Been Kissed, she landed roles in films including Sugar & Spice, Uptown Girls, Sin City, Death Proof, Planet Terror, W., and Scream 4. She most recently guest starred on an episode of Mad Men and had the lead role on the cancelled Lifetime series The Lottery. In 2001, she married her husband, film producer Beau Flynn, with whom she has two daughters, West (2009) and Ruby Jeanne (2012). In 2010, she was arrested for driving under the influence and was sentenced to two years of probation after pleading no contest. She will next appear in 2015's Solace with Anthony Hopkins and Colin Farrell.
8
James Franco
Never Been Kissed, James Franco
20th Century Fox via Everett Collection/WENN
James Franco is the sort of person that's so ubiquitous that it seems pointless to describe his career trajectory following his first film role in Never Been Kissed. He went on to play Harry Osborn in the Spider-Man trilogy, Flyboys, Knocked Up, Pineapple Express, Milk, Date Night, Eat Pray Love, Howl, 127 Hours, The Green Hornet, Your HIghness, Rise of the Planet of the Apes, Oz the Great and Powerful, This Is The End, As I Lay Dying, Palo Alto, Veronica Mars, The Interview, I Am Michael, with 13 other movies still listed as in production and another 15 movies releasing just this year. Franco was nominated for an Oscar for Best Leading Actor for his role in 127 Hours, has received a B.A. from UCLA, MFAs from Columbia University, New York University, Brooklyn College, and Warren Wilson College, and a PhD from Yale University. Franco has also been honored numerous times for his charity and philanthropic ventures. He also dabbles in seemingly everything: he's written books, directed and produced films, and has exhibited his artwork which includes videos, drawings, paintings, sculptures, and installations.
9
Jeremy Jordan
Never Been Kissed, Jeremy Jordan
20th Century Fox/IMDB
"Do I wanna be crunched?" "By Guy? Oh yeah." Jeremy Jordan's days as a teen heartthrob may be over now, but he has finally returned to acting. After Never Been Kissed, Jordan's acting career halted altogether until 2010. He's appeared in The Absent and Sin Verite. 16 years after releasing his first and only album, Jordan released a new song in 2009 about homeless people, appropriately titled "Forgotten People."
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10
John C. Reilly
Never Been Kissed, John C. Reilly
20th Century Fox/WENN
John C. Reilly's career only truly took off after his appearance in Never Been Kissed. After playing Josie's boss, Reilly starred in Magnolia and The Perfect Storm before having an incredible break-out year in 2002. That year, Reilly starred in 3 movies that received 32 Academy Award nominations between them, including one for Best Supporting Actor for Reilly: Chicago, Gangs of New York, and The Hours. He's also collaborated multiple times with Will Ferrell for hits like Step Brothers, Walk Hard: The Dewey Cox Story, Talladega Nights: The Ballad of Ricky Bobby, and Anchorman 2. He continues to appear in critically acclaimed films as well, ranging from Roman Polanski's Carnage to Disney's Wreck-It Ralph and Marvel's Guardians of the Galaxy. He and his wife also welcomed two sons after Never Been Kissed.
11
Molly Shannon
Never Been Kissed, Molly Shannon
20th Century Fox/WENN
The Saturday Night Live alumnus followed her role as Josie's best gal pal with the most iconic role of her career: Superstar. Though the movie wasn't well received, it remains synonymous with Shannon. She also made appearances in Will & Grace, How the Grinch Stole Christmas, Wet Hot American Summer, Shallow Hal, Sex and the City, My Boss's Daughter, Scrubs, Marie Antoinette, Talladega Nights: The Ballad of Ricky Bobby, Year of the Dog, 30 Rock, Evan Almighty, Glee, Neighbors from Hell, Bad Teacher, Enlightened, and Wet Hot American Summer: First Day of Camp. Molly Shannon also married artist Fritz Chesnut in 2004, with whom she has a daughter, Stella (born 2003), and a son, Nolan (born 2005).
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Octavia Spencer
Never Been Kissed, Octavia Spencer
20th Century Fox/WENN
Spencer followed her role in Never Been Kissed with small parts in a ton of movies, including Being John Malkovich, Big Momma's House, Spider-Man, Legally Blonde 2: Red, White, & Blonde, Bad Santa, Win A Date With Tad Hamilton, Miss Congeniality 2: Armed and Fabulous, Beauty Shop, Drag Me To Hell, and Seven Pounds. Then, someone finally realized that she's incredible, so they cast her in her Oscar-winning role in The Help. Now, she's keeping busy with her roles in Fruitvale Station, the Divergent series, and she starred on the short-lived Red Band Society. In 2013, Spencer published the first of her children's book series.

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