Pop singers heading into the movies has long been a contentious point, with some proving themselves capable (David Bowie in The Man Who Fell to Earth, Roger Daltrey in Tommy, Sting in Brimstone & Treacle), and some just flat-out dreadful (Britney Spears in Crossroads, Mick Jagger in Freejack, Madonna in anything).

But my vote for best crossover act would have to be Diana Ross in Sidney J. Furie’s Lady Sings the Blues (1972)—out on DVD this month—in which the Motown diva superbly portrays the late blues singer Billie Holiday. Ross had rich material to work with, given that Holiday’s talent was matched by her tumultuous private life. While the film is undoubtedly sad, compounding it is the fate of Ross. After this Oscar-nominated debut, she and co-star Billy Dee Williams reunited for Mahogany (1975), surely one of the worst films made in the ’70s, followed by The Wiz (1978), a stunningly bad all-black version of The Wizard of Oz. That one-two punch effectively sunk her acting career for good. —Matthew Hays