8. HENRY STARR (1874-1921)

Calling Card: Starr was known for his boldness, robbing banks in broad daylight despite his "wanted man" status.
Casualties: He killed officer Floyd Wilson in a gun battle.
Complex Says: Henry Starr was a career criminal, with a run that lasted over 30 years. During that time it was estimated that he robbed over 21 banks and pocketed $60,000 in cash.

But forget all of that. You know what makes Henry Starr really gangsta? During his run, he actually starred in a silent movie about his criminal escapades called A Debtor to the Law, which, come to think of it, kind of makes him the world’s first reality star.