When: 1949 -1951

The world was Frank Sinatra's playground during his prolific run. Ol' Blue Eyes settled down with his first wife Nancy Barbato in 1939. The marriage begat three children, but that couldn't stop the singer from straying into extra-marital affairs. Sinatra's infidelity became public knowledge when he was seen with a myriad of young singers and actresses, one of whom was the incomparable Ava Gardner.

Frank eventually left Nancy for the popular actress in 1950. The two tied the knot in November 1951, just ten days after the divorce from Nancy was complete. Ava and Frank's marriage wasn't exactly rainbows and butterflies, however. After the initial thrill and infatuation wore thin, all that remained were two hugely famous celebrities and their equally inflated egos. The pair called it quits in 1957.