#17: Frank Sinatra and Nancy Barbato (1951)
Frank Sinatra’s divorce from his first wife, Nancy Barbato, cost him dearly, both financially and emotionally. He had to make a settlement with Nancy for everything they owned, including their house and car, in order to marry Ava Gardner. Sinatra’s career was stumbling at the time and this payout nearly bankrupted him. This divorce was a turning point in Sinatra’s public persona, turning him from the charming crooner into the “bad boy” of Old Hollywood.

