#50. Vans Woodstock
In the early ’90s we were introduced to a clown of a skateboarder named Simon Woodstock. His talentless efforts on a skateboard got him nowhere, but when he dressed up as a clown or in a wet suit, or hopped into the ring for a boxing match, the public loved him. He became the highest paid skateboarder of the time, and this signature model goes to show that sometimes you need to check yourself. Or maybe you don't.