Legendary swashbuckling romantic leading man. By the late teens, Doug was such a popular actor that he was able to form his own production company. In 1917, while on a War Bonds tour with Mary Pickford and Charlie Chaplin he fell madly in love with “America’s Sweetheart” Mary. As the both of them were married at the time, their romance was one of Hollywood’s best kept secrets. In 1920, they divorced their partners, got married and became the ultimate power couple, America’s early equivalent to Aniston & Pitt and then some. He and Mary also made one picture together, ‘Taming of the Shrew’ in 1929 and Fairbanks was the co-founder of United Artists Pictures with Mary, Charlie Chaplin and D.W. Griffith, a studio now owned by Tom Cruise. The couple divorced in 1936, he married his longtime mistress Lady Sylvia Ashley (who later married Clark Gable). His health had also began to fail him and he began to experience heart problems. He died in his sleep of a heart attack at the early age of 56 and is buried in a huge crypt with a reflecting pool in Hollywood Forever Cemetery, later joined by his son, actor Douglas Fairbanks Jr.