Live Review: Jeffrey Ross Roasts Chicago

Stand-up/insult comic Jeffrey Ross, best known as the Roastmaster General from Comedy Central's series of Celebrity Roasts (Pamela Anderson, William Shatner, Flavor Flav, The Donald, etc) brought his lashing put-downs to Chicago for last night’s Just for Laughs appearance at the Vic.

Although billed as a roast of the Windy City, Ross meandered mostly back and forth between self-deprecation (“My doctor found a lump on my testicles—it was my dick. He said I should have it removed.”) and audience takedowns (to an excitable, “too-handsome-to-be-hetero” Quebecois bachelor party: “Celine Dion just had twins; that’s an achievement with that age—and with that face.”). Chicago did eventually get its turn with fat jokes, Oprah insults and “Your sports teams suck” material, the latter of which included a surprise appearance by a Cubs star.

Throughout the show, onstage guitarist Buddy played sound effects-like licks to emphasize Ross’s punch lines, although it became apparent fairly quickly that Ross, beer in hand, wasn't sure why the guitarist was there beyond serving as a Paul Schaeffer-like insult receptacle. Despite efforts to work the musician into the set, Ross didn't seem altogether prepared for more than his regular roast modus operandi: Three or four minutes of well-played, taboo-crushing insults.

Moments when Ross relied entirely on his improv skills proved to be the show’s highlights: He offered to "speed-roast" about fifteen audience members, ending up with a mix of volunteer targets too unremarkable to engage and easy-peasy roastables, the latter of which included Larry-the-Cable-Guy's dumber brother (and surprisingly attractive girlfriend), Gilbert Gottfried's "retarded" cousin, a hairy Harry Potter, and a heavyset woman with a red Mohawk who good-humoredly encouraged the comedian’s lashings.

The city’s turn over the spit did come eventually, starting with the “Castro of talk shows,” Oprah Winfrey (sample joke: a suggestion that the Harpo leader’s honorary street went from wide to narrow and wide again). Some predictable “You all are fat animals” material followed, before an expected but well-done succession of sports kickers that brought Cub’s pitcher Ryan Dempster on stage. (The good sported baseball star dutifully zinged Ross as he exited: “Please remember the environment and recycle, like Jeff does with his jokes.”). 

All said, Ross’s set lacked the focus of seasoned stand-ups, and his heavy reliance on improvised material—which, hit or miss, still pleased the crowd—left the show feeling disjointed at times, with jokes failing to flow into one another naturally. But for Ross, an audience that seemed almost more eager to please him than vice versa, along with a respectable number of golden moments born of his quick, ruthless size-ups, served him well. 


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Laura Baginski, Editor (@TimeOutChicago)