23. Frank Sinatra – 4

It’s not too surprising that a guy like Frank Sinatra was a total heartbreaker, is it? Sinatra first married Nancy Barbato (pictured) in 1939 at the age of 24. They were married for an impressive 12 years but then divorced in 1951 after some shady activity on Sinatra’s part. In the same year, he married Ava Gardner, and they divorced in 1957. He was engaged to two different women after that but never went through with the marriages. In 1966, he married model Mia Farrow, divorced her two years later, and then married his final wife, Barbara Marx, in 1976.