Most of Dawson's early work consisted of comedy sketches in which he would play original characters, impersonate celebrities, and make light of popular culture. Some of these impressions later drew criticism for their offensive content, including racial stereotypes. He has released six original songs such as "Superluv!" and numerous parodies of popular music videos. In 2013, he started the podcast Shane and Friends, which ran for 140 episodes over four years. In 2014, he directed, produced, edited, and starred in the romantic comedy film Not Cool and appeared on the accompanying docu-series The Chair. He has also appeared in the horror film Smiley (2012) and the comedy film Internet Famous (2016).
