Lifespan: 2008-present
Reminds us of: A bushy eyebrow

We're going to go ahead and count the 'stache as a hairstyle for this one just because it's so damn ridiculous. As soon as the former Def Comedy Jam comic shaved his head (but kept the tickler), he assumed he could confidently dole out life advice to women, via self-help books, and bad Tyler Perry-knockoff movies. That alone earns him a spot here.