Julia Roberts and Kiefer Sutherland — 1990

Ages: 22 and 23

Nominee: Actress in a Supporting Role, Steel Magnolias #Fact: This one’s juicy. Soooo, Julia and Kiefer met on the set of Flatliners, and they eventually fell in love IRL. The problem was, Julia was already engaged to Dylan McDermott, who played her husband in Steel Magnolias. Kiefer was married to his first wife, Camelia Kath. Kiefer’s divorce was finalized in early 1990 and Julia and Kiefer got engaged the same year this photo was taken. But it’s not over yet! Julia called off the wedding in 1991, just days before she was supposed to walk down the aisle. YIKES.