Whatever It Takes (released in theaters on March 24, 2000) follows Ryan Woodman, a nerdy, accordion-playing high school senior played by Shane West, who is hopelessly infatuated with the school’s most popular girl, Ashley Grant (Jodi Lyn O’Keefe).
The plot kicks into gear when Ryan strikes an unlikely bargain with the arrogant star athlete Chris Campbell (James Franco).
Chris is obsessed with Ryan’s lifelong best friend, the intelligent and soulful Maggie Carter (Marla Sokoloff), but lacks the depth or vocabulary to impress her.
The two boys agree to help each other “win” their respective dream girls: Ryan ghosts-writes romantic emails and poetic gestures for Chris to use on Maggie, while Chris gives Ryan a makeover and provides social coaching to get him into Ashley’s elite inner circle.
As the scheme progresses, Ryan finds himself successfully climbing the social ladder.
However, as Ryan spends more time pretending to be someone else to impress Ashley, he begins to realize that his true connection has always been with Maggie.
The deception reaches a breaking point at a massive graduation party, where the superficiality of Chris and Ashley is exposed, forcing Ryan to decide if popularity is worth losing the person who actually knows him.
Aaron Paul, Richard Schiff, Colin Hanks, Kip Pardue, David Koechner, and Nick Cannon round out the supporting cast.
The film serves as a quintessential example of the late-90s and early-2000s trend of updating classic literature for the MTV generation, in this case, a loose adaptation of Cyrano de Bergerac.
Franco delivers a standout, high-energy performance that hints at the comedic range he would later develop in his career, while West provides a likable, vulnerable lead.
The chemistry between West and Sokoloff gives the film its emotional heart, ensuring that the romantic stakes feel genuine amidst the era’s typical slapstick humor and teen movie tropes.
Jodi Lyn O’Keefe in Whatever it Takes (Photo/Sony Pictures)
Reception for Whatever It Takes
Whatever it Takes grossed $4.1 million on its opening weekend, finishing sixth at the box office.
The film would gross $9.9 million worldwide.
Legacy
Whatever It Takes‘ legacy is firmly rooted in its status as a time capsule of Y2K pop culture and its incredible “before they were famous” ensemble.
It remains a nostalgic favorite for those who grew up during the peak of the teen movie renaissance, particularly noted for featuring early roles for future Emmy winners Paul and Franco.
While it followed the established formula of its contemporaries, the film is remembered for its earnest charm and its attempt to blend classical romantic themes with the frantic, neon-soaked energy of a turn-of-the-century high school.
Whatever It Takes continues to be revisited by fans of the genre as a lighthearted, quintessential piece of millennial cinema that captures the awkward transition from adolescent pretense to authentic self-discovery.
