Day: April 3, 2008

Carolines closed out its second annual March Comedy Madness on Tuesday night with two very intriguing Final Four matchups. One half of the bracket pitted boyfriend against girlfriend, while the other half could best be described as the single white guys uncomfortable with the ladies division. Comedians performed with a scoreboard clock ticking behind them, as well as his or her competition sitting and/or standing on the side of the stage. First semifinal: Boyfriend against girlfriend, aka Reese Waters vs. Liz Miele. Waters (pictured) went first and, after a hesitant first 30 seconds warming up to the crowd, he really delivered with a fresh and funny take on Obama vs. Hillary and picking between a black man and a white woman, spinning it in turn on the audience’s choice between himself and Miele. Miele’s best jokes, coincidentally, came late in her five-minute set with bits about dating a black guy (though she never name-checked Waters specifically). Second semifinal: Single white guys uncomfortable with the ladies, aka Dan Hirshon vs. Rob O’Reilly. Hirshon went with awkward and insecure, while O’Reilly went with overcompensating overconfidence. Hirshon also talked about his Jewishness with bits about failing an audition for an extra in The Departed and working at Bertucci’s. O’Reilly opened strong with an act-out joke about having sex and being farsighted, then kept talking about sex. The finals: Waters vs. O’Reilly. But...