As far as 1990s dreamgirls go, Heather Graham was at the top of the list for many of us. An ageless beauty who looks the same as she did twenty-five years ago, Graham has one of the most interesting careers of the era. Having started as the love interest in the Corey Haim/Corey Feldman teen cult classic Licence to Drive, she quickly established her serious acting chops in 1989’s Drugstore Cowboy. The movie helped launch her as an indie “It girl,” with her landing memorable roles on Twin Peaks (and the Fire Walk With Me movie), Six Degrees of Separation and more. She had a unique role as the object of Jon Favreau’s affections in Swingers but then hit the big time with her iconic part as Rollergirl in Paul Thomas Anderson’s Boogie Nights.

This movie led to her getting a lot of big roles in the years that followed,...