Frank Sinatra, 4 Times
Source: https://www.grammy.com
Ol’ Blue Eyes, as Frank Sinatra is known, didn’t just have a talent for singing his heart out, but apparently he was fond of getting married too! Having been wed 4 times in his lifetime, the crooner may have been a legally married man, but he was also known for the number of affairs he had, which happened to be the reason why his first marriage ended. Amazingly, he remained good friends with his 2nd and 3rd wife, but it was his marriage to his 4th wife that lasted the longest, from 1976 until Sinatra’s demise.