Caligula

Anthony Jeselnik does not care if you like him. He practically insists you don’t. Pacing the stage with an arrogant smirk, he spends an hour setting up what feel like standard, sometimes somber premises, only to drop the floor out from under the audience with the darkest misdirection possible. He operates like a magician doing a card trick where the reveal is always a tragedy, turning taboo subjects into tightly constructed one-liners. The tension doesn’t come from whether he will cross a line, but how precisely he plans to step over it.

Filmed at the Vic Theatre in Chicago in 2013, Caligula captures Jeselnik during a major career transition. He was riding a massive wave of momentum from his breakout appearances on the Comedy Central Roasts of Donald Trump and Charlie Sheen, and this hour aired just before the launch of his own network series, The Jeselnik Offensive. The set is packed with his signature dark misdirection, including a memorable closer about a “shark party” and a casual complaint about a girlfriend who owns so many shoes it looks like she robbed the Holocaust Museum. Caligula landed on multiple year-end lists, proving his abrasive, joke-dense format could easily carry a theater crowd.