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Jeselnik is known for his dark comedy style, which emphasizes misdirection and sociopathic non-sequiturs. For his standup performance, Jeselnik adopts an arrogant, villainous persona.Jeselnik was a writer for Late Night with Jimmy Fallon in its first season and hosted a Comedy Central Presents in 2009. After releasing his critically acclaimed debut album Shakespeare in 2010, he began writing for the Comedy Central Roasts and moved up to performer in the 2011 roast of Donald Trump. He continued to perform on the roasts of Charlie Sheen and Roseanne Barr in 2012. In 2013, Jeselnik began hosting his own television series, The Jeselnik Offensive, and released his second album, Caligula, which doubles as an hourlong standup special