The Simpsons Season 2 Episode 8

Inspired by Evel Knievel-type daredevil Lance Murdock, Bart decides to spend his free time doing stunts with his skateboard. Despite a early trip to the hospital, he continues to show off and thrills his classmates to no end. But when he suspects his act may be going stale, he announces that he'll perform the greatest stunt possible -- a leap off of SPRINGFIELD GORGE!