Janet Jackson – 53 years old
Starting with her third album, 1986’s Control, the youngest Jackson sibling — now a Rock and Roll Hall of Famer — has placed in the top two on Billboard‘s Top 200 album chart eight times in a row, with five going multi-platinum. After appearing in her brother Michael‘s summer 1976 CBS variety series, she started her career not as a singer but as an actress, with roles on TV’s Diff’rent Strokes, Good Times and Fame. She also starred in Poetic Justice and Nutty Professor Two: The Klumps. Janet started the biggest non-military controversy of 2004 when Justin Timberlake helped her with the “wardrobe malfunction” that exposed her breast on live television during the Super Bowl halftime show.