Trendsetter: N.W.A. 

Long before Don C. came out smashing the game with custom snapbacks and before we had to deal with songs like "Snapbacks and Tattoos," there were some real ass dudes starting this cool cap phenomenon. Pre-PG-movie-Ice Cube, N.W.A. held the spot for the most respected rap group in the '80s you'd be crazy to look sideways at, so when they started rocking snapbacks to represent their neighborhoods and local teams, people jumped on that trendy bandwagon quick. Was it out of respect or fear? We'll never know.