Year: 1987
Lost to: Paul Simon, Graceland
Other nominees: Peter Gabriel, So; Barbra Streisand, The Broadway Album; Steve Winwood, Back in the High Life

Janet Jackson’s third album, 1986’s Control, marked not only Jackson’s freedom from her family’s control over her career (her early releases were overseen by her father), but also her explosive breakthrough into the mainstream. The Jimmy Jam- and Terry Lewis-produced R&B opus took risks that paid off, innovatively combining new-jack swing, funk, disco, and rap, along with spectacularly choreographed, super-stylish music videos that showed off her dance skills and made her an MTV staple. It was futuristic but relatable, empowering but a little nasty, and it went five-times platinum, selling over 14 million copies worldwide. Jackson was nominated for three Grammys in 1987 (Album of the Year, Best Female R&B Vocal Performance, and Best R&B Song, for “What Have You Done For Me Lately”), but didn’t win any of them; Album of the Year went to Paul Simon for his admittedly excellent sixth album, Graceland. But Jackson went on to make Grammy history many times over the course of her achievement-filled career: She became the first female artist to be nominated for Producer of the Year in 1990, for her fourth album, Rhythm Nation 1814, and she remains the only artist in Grammy history to receive nominations across five different genres (Pop, Rock, Dance, Hip-Hop, and R&B).