Sonny Bono & Cher – $364 Million

During his childhood, Sonny Bono already had a definite goal for his future: to become a successful singer. At 16 years old, he made the song Koko Joe, which was eventually covered by more than a few artists since its release. Along the way, while he was still making his way into the spotlight, Sonny also worked a variety of jobs, including waiter, construction laborer, and taxi driver. Well, in retrospect, it’s safe to say that all his investments surely paid off in the end.

From 1964 to 1975, Sonny was married to fellow singer Cher. Like Sonny, Cher also developed a passion for music and acting at a young age, having performed in a few of her grade school’s musical productions. The two also released records together as Sonny & Cher, with their song, I Got You Babe, reaching the number-one spot on the charts upon release.