Mixing snarky comedy with self-conscious sensitive-guy music is always a risky proposition. So when Smug Shift creators Moshe Kasher and Brent Weinbach put crooners Bart Davenport and Liam Carey on a comedy bill that included such nuts as Will Franken and Drennon Davis, they knew they were standing on shaky ground from jump. -- Rachel Swan Nonetheless, Kasher and Weinbach had the foresight to make Carey and Davenport bookend the show, so as not to disrupt a sequence of increasingly strange and out-there comedians. Neo-folk artist Carey opened around 9 p.m. for an almost packed house of disaffected hipsters, who brightened once the comedy got under way. Our two hosts did a mock freestyle battle in which they rhymed "East Bay Express" with "homosexual sex" -- among other things -- and got so snitty with each other that at one point it seemed like they were actually coming to blows. Audience members laughed uneasily, as if bracing themselves for a very tense show. But Santos lightened everything up when he opened the showcase with a set borrowed from the Margaret Cho playbook -- complete with an officious, if clueless, Asian immigrant woman, and a gay guy caricature that more closely resembled the Shanaynay character from Martin. He was followed by newbie Mary Van Note, playing a raunchier version of Christina Ricci. YouTube hotshot Drennon Davis burbled racist kindergarten songs and did an uncanny impression of Seal singing Stop looking at my over-accented scars.
Then came the more established yuksters: Weinbach, who carefully writes all his jokes ahead of time and spends years refining them (and does an amazing self-caricature); Kasher, who often speaks off the cuff, hectors his audience, and insists he's more concerned with being "funny" than being a genius; and Franken, who's graduated from telling stories to making up characters and inhabiting them. Davenport, who came with a rousing endorsement from sometime-jazz pianist Weinbach, is one of the few local indie musicians with enough chops to follow such an incredible lineup, even though he changed the mood on a dime that night. Slight and wiry with a '70s-mod haircut, he looked and sounded almost exactly like Barry Manilow, and made no bones about it. After all, Davenport is definitely the most swaggeringly confident, irony-deficient version of Manilow you've ever seen. Warbling carefully-crafted lyrics over soca-cabana guitar strumming, he had an anomalous presence in an otherwise archly humorous showcase. But Davenport played well enough to convince some of us that the comedy-music thing can actually work. And he kept playing, even as the crowd thinned out.