High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.
Sound
Fatboy Slim and Sixpence None the Richer = prom canon.
Costume
Laney's 'ugly' overalls are literally just... overalls.
Writing
Brock Hudson: reality TV's first true villain.
Director
Robert Iscove
Freddie Prinze Jr.
Zach Siler
Rachael Leigh Cook
Laney Boggs
Paul Walker
Dean Sampson
Jodi Lyn O'Keefe
Taylor Vaughan
Kevin Pollak
Wayne Boggs
Anna Paquin
Mackenzie Siler
Kieran Culkin
Simon Boggs
Elden Henson
Jesse Jackson
Matthew Lillard
Brock Hudson
Usher
Campus D.J.
Lil' Kim
Alex
Gabrielle Union
Katie
Dulé Hill
Preston
Tamara Mello
Chandler
Clea DuVall
Misty
Trivia, insights & behind the scenes
This Pygmalion retelling spawned a generation of 'take off her glasses, she's beautiful' tropes that we're still unpacking. The 2021 gender-flipped remake He's All That proved the formula's... resilience?
The 'dancing at the house party' scene was choreographed by Adam Shankman, years before he directed Hairspray. Those synchronized moves? Pure early-2000s music video DNA.
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