15John Mayer

John Mayer is one of the music industry's most notorious playboys. Since his music career kicked off in 1998, John has had his fair share of famous girlfriends. Jessica Simpson, Jennifer Love Hewitt, Katy Perry, and Jennifer Aniston have all dated him. He has also been linked to Taylor Swift,

Kim Kardashian, Cameron Diaz, and Miley Cyrus. Unfortunately, his reputation with the ladies is not squeaky clean. Many of his exes have accused him of cheating, and his alcohol dependency didn't help matters of the heart. Things seem to be shaping up for the 40-year-old singer, however. He recently celebrated one year of sobriety, and he seems to be taking a break from dating to focus on his wellness. Maybe this bad boy has found redemption!

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