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In Crimes and Misdemeanors, Alan Alda’s unctuous producer character, Lester, summarizes his theory of black comedy thus: “If it bends, it works; if it breaks, it doesn’t work.” The humor of Neil Hamburger, arguably the best bad comedian this country has ever produced, doesn’t just break—it shatters, spills, and leaves a stubborn stain on your psyche. Dropping hilariously unfunny platters on the public since 1996, Hamburger has turned the act of bombing onstage into a sublime art form. He has caused hipsters to upgrade their smirks to guffaws through his flubbed delivery, harrowing self-deprecation, and tweaking of comedy’s tropes. His topical jokes are long since past their expiration dates, and some of the skits on his recordings are visual jokes that (intentionally) don’t quite survive the transition: Take, for example, his extended silent balloon-sculpture bit, “The X-Rated Hot Dog Vendor,” which is the comedy equivalent of John Cage’s “4′ 33″.” But in spite of his deficiencies, Hamburger occasionally scores a true zinger: “Why did God invent Fleetwood Mac? Because he was high on PCP.” The down-on-his-luck jester has continually tried in vain to revive his flagging career by dabbling in genre humor—impersonations, blue humor, and (on his most recent release, Laugh Out Lord) religious humor. He often seems to forget, however, that he’s doing a religion theme and has to shoehorn the churchy jokes at the last minute: “Why did God invent Alan Alda? Because He needed some way to transport Golden Globes awards into Hell.” The uncomfortable silence that follows a joke like that is truly the sound of something breaking. Hamburger performs with Canned Ham at 9 p.m. Monday, July 21, on the Black Cat’s Backstage, 1811 14th St. NW. $7. (202) 667-7960 (David Dunlap Jr.).