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.

Reesewaters
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 first, 2007 March Comedy Madness champ Julian McCullough returned for a guest set while the semifinal votes were tallied. An odd decision for two reasons: 1) McCullough hit strong, making the finals a bit weird because the audience now would subconsciously be comparing the finalists to him, and 2) when the finals kicked off, O’Reilly and Waters would restart not only cold, but also without any of their better jokes from their earlier sets to use in a new 10-minute set.

That said, O’Reilly went dirty and racial, whereas Waters followed with a more personal approach talking about growing up black and poor. Waters made that connection with the audience (not that they were made up of poor, black people, but that he made audience members feel more comfortable about laughing, and therefore voting for him), and won. The Carolines contest format made me think about the San Francisco and Seattle comedy competitions, in that anyone can advance in an early round with a great joke or short set (for Carolines, the initial battles were decided by a 1-minute bit and a decibel reader!), but that comedian with a solid 4-5 can collapse in the finals (where in Seattle and SF, you’ve got to prove you have another solid 20 or more minutes).

So O’Reilly finishes second for the second year, and Waters, for his victory, gets a paid week opening at Carolines, a trophy and an interview with ABC.com and ABC News Now.

Earlier this month, ABC News Now featured McCullough. Here’s a link to the video (embedding? anyone?). I’ll upload the video with Waters when it becomes available. Also, fun to note in McCullough’s performance that they have him play to such a small crowd in a TV studio. That’s always a fun time, isn’t it? But he does get them going eventually. And Caroline herself is there, too!