Character: Ash Ketchum
Video Game: Pokémon (1996)

You wanna be the very best, like no one ever was? Better cuff your pants and flip your snapback backwards. Ash Ketchum did that when it was time to battle, and we see skater kids and streetwear heads do the same too. It's a good look whether you're about to get gnarly on a board or whip our your illest Pokémon card. Nothing strikes more fear into your opponent quite like that backwards cap turn when you're about to throw down your Charizard against his Jigglypuff.