“We have to have this for the house in Fire Island!” A diminutive young woman, small even in her heels and shining silk tent dress—crammed with other bad-art lovers into the lavish Hiro Ballroom on a Tuesday night—pointed excitedly toward the stage with her paddle, indicating a small painting of a hunky merman that was being hawked by the evening’s antagonistic, heavily bearded auctioneer. The picture appeared to be painted on a piece of cheap canvas, perhaps by a teenager in a mandatory high school art class. A male companion seemed to agree with the young woman’s sentiments, and, after accidentally raising his glass to bid, he raised his paddle, kicking off an intense bidding war and eventually scoring the merman for a cool $200.

This kind of so-kitschy-how-did-I-ever-live-without-it sentiment was de rigueur at the New York by New York Bad Art auction, which benefited New York Cares, a volunteer-based charity aiding people all over New York City. The auctioneer and master of ceremonies was Zach Galifianakis, a comedian specializing in politically incorrect humor à la the queen of dirty jokes, Sarah Silverman (whose show he’s appeared in). His abrasive epithets only spurred the audience—greased by the complimentary Pom Tea cocktail with your choice of vodka or Jack Daniels—to the highest level of irreverent philanthropy.

The audience’s desire to spend big bucks on bad art became manifest toward the end of the night when a framed poster of Nascar superstar Richard Petty (at right) brought in $500. An image of a vintage Walt Disney pig also caused quite a scene; it was sold by dance-music star Moby, who, from a banquette off to the side of the room, demonstrated to the cheering crowd that the pig was actually—in addition to being one of the only foam-on-plywood paintings in the 50 states—inflatable, and a steal at $300.

The evening ended with Seattle-based indie-rock darlings Band of Horses playing a full set for the giddy crowd. A disco ball spun lights around the merman, who, being passed over the heads of his new owners, had become a Fire Island-bound crowd-surfer for a good cause.

—Maud Deitch Rohrer