Margera began filming himself and his friends skateboarding and doing stunts and released a compilation of his work as CKY:Landspeed in 1999. CKY2K, CKY3 and CKY4 have also been released. CKY stands for "Camp Kill Yourself", a reference to the film Sleepaway Camp. These early videos feature many of Margera's friends, including Ryan Dunn, Brandon DiCamillo, Rake Yohn, Chris Raab, Brandon Novak and others who form a loose collective known as the CKY Crew. CKY is also the name of a rock band featuring his brother Jess (see CKY (band)), and the history and relationship between the video and band projects is heavily interlinked.

Former Big Brother editor Jeff Tremaine noticed Margera's videos and drafted him into the team which would eventually become MTV's Jackass. Margera and Ryan Dunn became mainstays of the cast while other CKY crew members played supporting roles to various degrees. Margera went on to appear in both Jackass: The Movie and Jackass Number Two. Several skits in t