Oona O’Neill and Charlie Chaplin
As the beautiful teenage daughter of playwright Eugene O’Neill, Oona O’Neill was a New York “it” girl in the 1940s, dating, among others, Orson Welles and J.D. Salinger. Alas, she broke Salinger’s heart when, at 16, she ended the relationship to be with Charlie Chaplin, who was then in his early 50s. After she married Chaplin in 1943, following her 18th birthday, Eugene O’Neill cut his daughter out of his life because he did not approve of the relationship. And yet the marriage lasted for 35 years—producing eight children—until the actor’s death in 1977 at 88.