Crossroads (2002)

Synopsis
Multimillion-selling recording artist Britney Spears makes the transition to the big screen with this teen road trip romantic comedy, co-produced by the film branch of the entity that first brought her pop stardom, MTV. Crossroads casts Spears as Lucy, the shy valedictorian of her high school graduating class. On the night of their prom, Lucy and her once-close childhood friends -- the prim and proper Kit (Zoe Saldana) and the tomboyish, five-months-pregnant Mimi (Taryn Manning) -- reunite to dig up a time capsule they buried together as little girls. Mimi's about to make good on her childhood dreams; she's leaving their small Southern town for hopes of fame and fortune in Los Angeles. Though Lucy and Kit are reluctant to join her, they decide to tag along at the last minute, agreeing to be chauffeured by Mimi's just-out-of-jail friend, Ben (Anson Mount). As they trek across the country, plagued by car problems, unsanitary motels, and petty bickering, the three friends reveal meaningful secrets to each other, and Lucy begins to realize that the handsome, reticent Ben might just be the guy for her. ~ Michael Hastings, All Movie Guide