Released in 2002, Crossroads was Britney Spears’ first and only feature film. The coming-of-age dramedy, which was directed by Tamra Davis and written by Shonda Rhimes, came out at the height of the pop star’s career: In the previous year, she had performed at the Super Bowl, signed a multi-million-dollar promotional deal with Pepsi, and released her third studio album Britney. (Her fourth, In the Zone, followed close behind in 2003.) The film follows three childhood friends (played by Spears, Zoe Saldana, and Taryn Manning) who, after years apart, embark on a cross-country road trip. Its soundtrack is fittingly rife with the timeless anthems, feel-good fare, and 2002-timestamped hits you sing in the car while cruising down the freeway or in the middle of nowhere. Shania Twain’s female-empowerment bop “Man! I Feel Like a Woman!” kicks off an eclectic mid-soundtrack run that includes The Cult’s howling “Rise,” Marvin Gaye’s sensual soul classic “Let’s Get It On,” and Sheryl Crow’s raspy “If It Makes You Happy”—a soaring ode to owning your life’s choices. Crossroads’ soundtrack would be incomplete without some of Spears’ own songs. There’s Richi Lopez’s remix of “Overprotected,” the rebellious cry of every teen demanding independence. She’s playful and seductive, self-assured and edgy on “I Love Rock ’N’ Roll” (a cover of Alan Merrill and Jake Hooker’s 1975 song, made famous by Joan Jett & the Blackhearts) with her growling choruses and kittenish ad-libs. But the star here is “I’m Not a Girl, Not Yet a Woman,” an introspective guitar ballad that captures the movie’s premise: the pain and beauty of transitioning into adulthood. Looking back at the turbulent years that followed, her lyrics become more heartbreakingly poignant: “I'm just tryin' to find the woman in me/All I need is time, a moment that is mine/While I'm in between.”