Fresh off of the release of 2001's Britney, and already with ...Baby One More Time and Oops!... I Did It Again to her name, Britney Spears led Crossroads as Lucy Wagner. In one of her first acting roles, the pop princess played a high-achieving high school student who heads west to search for her mother and finds herself along the way. While she famously focused on her music career after her turn as Lucy, Spears still acted from time to time, popping up in episodes of Will & Grace, How I Met Your Mother, and Jane the Virgin.