In 1999, 'Drive Me Crazy' capitalized on the height of teen rom-com mania, pairing Melissa Joan Hart and Adrian Grenier as lifelong friends and opposites who decide to date in order to make heads turn and attract the attention of their respective objects of affection. With an accompanying title song by pop star Britney Spears, the film was a smash hit -- obviously. This year, 'Drive Me Crazy' celebrates its 15th anniversary, and we take a look back at the cast of this teen classic to see what they're up to now. 

Melissa Joan Hart, Nicole Maris

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Then: Former 'Clarissa Explains It All' star Melissa Joan Hart played Nicole Maris, a popular high school girl who pines for the school's star basketball player, so she decides to date her next door neighbor and lifelong best friend in order to make him jealous. At the time, Hart was also starring on the teen sitcom 'Sabrina, the Teenage Witch.'

Now: 'Sabrina, the Teenage Witch' ended its run in 2003, and Hart went on to have an uncredited cameo role in the teen rom-com spoof flick 'Not Another Teen Movie.' She's appeared in a handful of TV movies, including 'Holiday in Handcuffs' and 'My Fake Fiance.' She lent her voice to a couple of episodes of the Adult Swim animated series 'Robot Chicken,' co-created by her 'Can't Hardly Wait' co-star Seth Green, and competed in the 2009 season of 'Dancing with the Stars.' Since 2010, Hart has starred on the sitcom 'Melissa and Joey' with fellow former teen star Joey Lawrence.

Adrian Grenier, Chase Hammond

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Then: Adrian Grenier was a fresh-faced newcomer when he was cast as Chase Hammond, the loner and rebellious activist whose girlfriend Dulcie dumps him, so he decides to pretend to date his friend Nicole to get her back. Grenier had previously appeared in the films 'The Adventures of Sebastian Cole' and 'Celebrity.'

Now: Grenier is, of course, best known for playing the lead role in the HBO series 'Entourage,' executive produced by Mark Wahlberg and loosely based on Wahlberg's own experiences as a rising star in the film industry. Grenier has appeared in the films 'Cecil B. Demented,' 'A.I.: Artificial Intelligence,' 'Anything Else,' and 'The Devil Wears Prada.' Up next, he appears in the apocalyptic indie 'Goodbye World,' and stars in the 'Entourage' movie.

Susan May Pratt, Alicia DeGressario

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Then: Susan May Pratt played Alicia DeGressario, Nicole's frienemy and rival for star basketball player Brad's attention. Pratt also appeared in the teen films '10 Things I Hate About You' and 'Center Stage.'

Now: Since then, Pratt hasn't done a whole lot -- she's appeared in the films 'Searching for Paradise' and 'Open Water 2,' and guest-starred on a handful of TV shows, including 'Private Practice,' 'Mad Men' (pictured above right), 'Franklin and Bash,' and most recently, an episode of 'Drop Dead Diva.'

Mark Webber, Dave Ednasi

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Then: Mark Webber played Dave, one of Chase's friends who runs a designated driving service and has been falling for a girl he talks to online -- turns out, that girl is one of Nicole's friends. Webber also appeared in the films 'Jesus' Son,' 'Snow Day,' and 'Boiler Room.'

Now: Since then, Webber's continued to gain a lot of indie cred with roles in films like 'Broken Flowers' and 'Good Dick,' the latter of which he starred in with his friend Jason Ritter. He's gotten more notice in recent years, with roles in 'Scott Pilgrim vs. the World' and 'For a Good Time, Call...,' as well as the indie dramedy 'Save the Date.' He also wrote, directed, and starred in the indie drama 'The End of Love,' in which he played a fictional version of himself alongside his real-life son and several of his actor friends also playing themselves. Recently, he appeared in the horror thriller '13 Sins,' and stars in the upcoming indie 'Laggies' with Keira Knightley and Sam Rockwell.

Kris Park, Ray Neeley

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Then: Kris Park landed his first major role as Ray Neeley, another of Chase's nerdy outsider friends. Park had previously had a minor role in the comedy 'Camp Stories' with Elliott Gould and Jason Biggs.

Now: Since then, Park has appeared in the films 'Bamboozled' and 'The Ordinary Sinner.' He studied acting at NYU's Tisch School of the Arts and at the American Academy of the Dramatic Arts in New York. He's appeared in several short films, including the 2013 short 'Chapel Perilous,' which won both the Audience and Short Film Grand Jury prizes at the 2013 Sundance Film Festival. Up next, he'll star in the indies 'The Gods of Garbage' and 'Hedda Gabler Shoots Again.'

Gabriel Carpenter, Brad Seldon

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Then: Gabriel Carpenter made his film debut as Brad Seldon, the school's star basketball player and the guy Nicole wants to date.

Now: Carpenter had minor roles in the films 'My Sister's Wedding' and 'Riding in Cars with Boys,' and appeared on a handful of shows, including 'Freaks and Geeks,' 'Sabrina, the Teenage Witch,' 'Boston Public,' and 'Law and Order,' but he seems to have stopped acting sometime in 2002.

Ali Larter, Dulcie

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Then: Ali Larter played rebellious activist Dulcie, the girl who breaks Chase's heart, inspiring him to pretend to date Nicole in order to make Dulcie jealous and get her back. Larter was an unknown who had a big break in 1999, also appearing in 'Varsity Blues' and the 'House on Haunted Hill' remake.

Now: Larter is also known for her roles in 'Final Destination,' 'Legally Blonde,' 'Jay and Silent Bob Strike Back,' 'Obsessed,' and both 'Resident Evil: Extinction' and 'Resident Evil: Afterlife.' In 2004, she reunited with Grenier to play herself in the pilot episode of 'Entourage,' and from 2006 to 2010, she starred on the NBC series 'Heroes.' She recently guest-starred on an episode of 'The League,' and can be seen next in the upcoming sixth 'Resident Evil' film, as well as the movies 'You're Not You' and 'Lovesick.'

Lourdes Benedicto, Chloe Frost

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Then: Lourdes Benedicto played Chloe Frost, one of Nicole's friends. Benedicto had a recurring role on 'NYPD Blue' and previously appeared in the film 'Permanent Midnight.'

Now: Since then, Benedicto's only appeared in a handful of movies, including 'Two Days' and 'The Fighting Temptations.' She's had more success on television, with recurring roles on 'ER,' 'Dawson's Creek,' '24,' 'The Nine,' 'Cashmere Mafia,' and 'V' -- though her last few shows were short-lived. More recently she guest-starred on an episode of 'NCIS.'

Keri Lynn Pratt, Dee Vine

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Then: Keri Lynn Pratt made her acting debut as Dee Vine (real name: Judy), who has secretly been involved in an online relationship with Chase's friend Dave, though the two are unaware of each other's real identities.

Now: Pratt also appeared in the oft-forgotten teen film 'The Smokers,' as well as 'America's Sweethearts,' 'Fat Albert,' and 'A Single Man.' She reunited with Melissa Joan Hart for an episode of 'Sabrina, the Teenage Witch,' and has appeared on a ton of television shows over the years, including 'That '70s Show,' 'Nip/Tuck,' 'Veronica Mars,' and she had a recurring role on the short-lived series 'Jack and Bobby.' In more recent years, she's lent her voice to an episode of 'Family Guy,' guest-starred on 'The Mentalist,' and had a recurring role on 'Smallville' as Cat Grant.