39. Arsenio Hall
Why He Made The Cut: Late-night TV's daily dose of realness.
Arsenio Hall changed the late-night TV landscape with his talk show, but he also knew how to stunt. Take for example, the wild ties he'd pair with simple suits. And when he felt like taking things to the next level, he'd rock multicolored leather jackets and bright-colored blazers. For a guy whose job was to let the guests shine, he certainly knew how to keep the attention on himself too.