‘She’s All That’ at 25: My fair ‘90s lady

Rachael Leigh Cook takes off her glasses, becomes hot, and falls in love

Image: Miramax Films

The 1990s trend of Shakespearean plays and other classic literature being loosely adapted into teen romantic comedies hit one of its biggest highs with She’s All That, a John Hughes-style re-imagining of George Bernard Shaw’s Pygmalion, and its own stage/film adaptation My Fair Lady. 

Directed by Robert Iscove, She’s All That arrived in theaters in January of 1999, 25 years ago this month. It was a sweet, entertaining high school rom-com, with a well-chosen cast filled top-to-bottom with current and future stars. But like many films from that decade, there’s a lot in it that doesn’t quite add up and lands with a thud to modern ears. And not only because of the word “Miramax” appearing on the poster.

Zack Siler (Freddie Prinze Jr.) is the high school alpha class president with family money and a staff of Ivy League acceptance letters in hand. His dad is even Eric Stratton, Rush Chairman (Tim Matheson).