Current Rank: 5

Timmy Jenkins used to stand out in skateboarder competitions as the kind of kid who nailed down tricks with backside lips on the flat bar and buttery frontslide flips. Considered a hungry competitor who could effortlessly pull out full-flay counter melons over the pyramid, his future on the circuit seemed assured. Then came the 1998 Tampa Am. He was tearing up the course with backside 360 boardslides and switch 180 grinds to revert. But he took a digger while doing nollie crooks on the flat bar and smacked his head on the rail.

Lying there, uncharacteristically motionless, Timmy had a demented epiphany. He was no longer Timmy Jenkins. He was Half Pipe. He was no longer interested in skateboarding competitions. He must destroy Shopping Carts. He stood up, grabbed his board and left the arena. The skateboarding circuit's loss, the supermarket world's nightmare.