40. Ice Cube
Why He Made The Cut: Not only was today a good day, the entire '90s was a good style decade.
He may have been one of the originators of gangsta rap, but what we loved the most about Ice Cube (that is, before he ever thought daddy movies were a good idea) was that he looked like every other dude from the hood. Jeans, a sweatshirt and a Raiders cap were really all you needed. Then, the lyrics can speak for themselves.