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She obtained her first lead role in a feature film on the teen drama Strong Island Boys, based on true events about a Long Island 80's street gang.Alec Baldwin gave her a favorable review—he called her "a cross between Debra Winger and Marlene Dietrich".Amazon High, which also was proposed as a third show set in the Hercules and Xena mythological genre, never has been aired.Later, portions of the pilot were adapted and edited into the Xena: Warrior Princess episode "Lifeblood" in 2000.

The short drama was shot in NYC and won multiple awards after its premiere in September 1998.The film received a limited release in September 2001, in New York and Los Angeles.She next starred as a college student having an affair with her professor in the controversial independent drama Storytelling, alongside Leo Fitzpatrick.Following several auditions, independent film roles, and guest-roles in television series, Blair achieved her breakthrough opposite Sarah Michelle Gellar and Ryan Phillippe in the 1999 coming-of-age drama Cruel Intentions, loosely based on the 18th-century novel Les Liaisons Dangereuses.Blair played the role of an innocent student manipulated by two of her classmates.