The Rat Pack is legendary for their antics. Aspiring bad boy Hollywood bro crews are still measured in relation to the Rat Pack's debauchery. Sinatra was a legendary womanizer. It's well-known that his four marriages were just the tip of the iceberg. Sinatra was linked to Judy Garland, Lauren Bacall, and Marilyn Monroe at different points in his romantic life.

He suffered from depression which often led to alcohol, pills, and fist fights. Sinatra's brawling history is almost comical, as he exchanged blows with everyone from airport employees to casino executives. Old Blue Eyes even had significant ties to organized crime. We can't understate "significant." The F.B.I. had almost 2,500 pages of information about his ties to the mob. "His way" apparently included the a path of self-destruction that few stars could ever hope to match.