After graduating from college, Sharp moved to New York.[2] In New York, Sharp met fellow comedians Bowen Yang, Matt Rogers, and Joel Kim Booster.[3] He also met Aaron Jackson through Langan Kingsley.[4] Sharp began performing with Upright Citizens Brigade in 2009.[5] He and Aaron Jackson collaborated on several comedy pieces, including the Funny or Die video Series "Jared & Ivanka."[6]
With Aaron Jackson, Sharp wrote and starred in the musical Fucking Identical Twins which played with Upright Citizens Brigade for more than a year. In 2016, the musical was optioned by 20th Century Fox for film adaptation.[9] The film, Dicks: The Musical, premiered in 2023.[10]