4. James Brown

If you thought “The Godfather of Soul” had an easy life, you’re mistaken. Aside from his successful career as a singer, James Brown was one bad boy off-scene.

Brown got pinched a number of times for assault, which usually involved his ex-wife Adrienne Rodriguez. However, this was not his greatest accomplishment in the law-breaking department.

James Brown was actually a part of a high-speed car chase between Georgia and South Carolina in 1988.

Ultimately, Brown was caught and arrested on multiple charges, like assaulting a police officer and weapons, drug, and driving offenses. This earned the singer 6 years in prison, of which he served only three before being released.

Total number of arrests: 8