From pushing around on a Pokémon complete from Target to skating Tony Hawk’s vert ramp nearly every day, Jimmy Wilkins’ skateboard journey has come a long way. In this Then/Now episode, he opens up about his first real setup, the chaotic music that defined his early skatepark days, and the unlikely Frank Sinatra and Biggie Smalls mashups he’s into now. He reflects on the VHS tapes he wore out and skate legends—Bob Burnquist, Chris Miller, and others—who shaped his journey. Hit play and hear it all from Jimmy.