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In 2008, when Dawson was nineteen years old, he signed up for YouTube and began making videos. He rose to fame on the site, garnering over half a billion views by 2010. Most of his early work consisted of sketch comedy videos, where Dawson would play original characters, impersonate celebrities and make light of popular culture. During this time, Dawson also had a short-lived music career, releasing 6 original songs such as "Superluv!" and numerous parodies of popular music videos. In 2013—inspired by Howard Stern—Dawson launched his podcast, Shane and Friends, which ran for four years and produced 140 episodes. The following year, Dawson released his first and only feature film, Not Cool, and appeared on an accompanying 10-episode docu-series The Chair.