A 2000 romantic comedy pairing Julia Stiles with Freddie Prinze Jr. as college sweethearts navigating young love in New York City. Released at the peak of the teen rom-com boom, the film cast Stiles as the grounded Imogen opposite Prinze’s smitten Al. It further established her as one of the most reliable young actresses of the turn-of-the-millennium era.
(David Shankbone / Wikimedia Commons (CC BY-SA 3.0))