Where: Everywhere

When: 2010-present 

To say Coolio is married to his braids is almost an understatement. The rapper had braids when he first hit the scene, though of course he actually had a head full of hair then. He's practically bald now but he's still holding onto his struggle braids. He just needs to let go and find a new look. Maybe he can take the advice Shaquille O'Neal gave LeBron James: Come home; bald is beautiful.