The 17-year-old actress, fresh from making her movie debut, looks ready to roll with the homies at the Clueless premiere beach party in 1995.
Brittany and her Girl, Interrupted co-star Winona Ryder get into the spirit after participating in a 2000 staging of Eve Ensler's The Vagina Monologues.
Brittany and Eminem were rumored to have hooked up while shooting the 2002 drama, but all the actress would ever say was that they had become very close. She did openly sing the rapper's praises, however.
"He's actually the most respectful person that I ever had a love scene with," she later said. "It's an extremely raunchy scene. It could have been an awful experience, but instead it was a very private, on a very closed set. Marshall was so overwhelmingly respectful; he didn't make dumb jokes as guys sometimes do when they're nervous on set. He didn't make me feel uncomfortable in any way."
The actress puts the squeeze on her Uptown Girls costar, Dakota Fanning, at a 2003 party for the movie at New York's swanky Henri Bendel store on Fifth Avenue.
"2day the world lost a little piece of sunshine. My deepest condolences go out 2 Brittany's family, her husband, & her amazing mother, Sharon," former boyfriend Ashton Kutcher tweeted upon hearing the sad news. The two dated back in 2003 after costarring in Just Married.
In 2004, the actress was briefly engaged to talent manager Jeff Kwatinetz before they amicably went their separate ways.
In May 2005, Mickey Rourke led his Sin City costar to a press appearance for the movie at the 58th International Cannes Film Festival in the south of France.
The Sin City star commanded the room at the 2005 MTV Europe Music Awards at the Atlantic Pavilion in Portugal.
The actress met production assistant Joe Macaluso on the set of her 2004 romantic comedy Little Black Book and they got engaged on New Year's Day 2006—but called it off that August.
Brittany put her best foot forward on the red carpet at the Hollywood premiere of Happy Feet in 2006 after giving voice to Mumbles' penguin sweetheart, Gloria.
Brittany swapped vows with British writer-director Simon Monjack "in a very intimate ceremony" at their West Hollywood home in April 2007, her rep told E! News at the time, after a whirlwind courtship, though they first met years prior when Monjack photographed her for Jane magazine.
"To make a long story short, I was very patient," he told the New York Post in 2008.
On Dec. 3, Brittany made what would be her last public appearance at the opening of Tt Collection's Popup shop in Los Angeles. "As far as having a New Year's resolution, I'd love to have a child next year," she told Access Hollywood at the event. "But that's kind of a large one!"