It may have been the most innocent of alcohol-swilling madhouses the Lower East Side has seen for a while.

A line stretched down the block—even after the PBR open bar had ended!—with a “Happy Little Raffle” to benefit a local arts charity, landscape painting tutorials, and the "world’s first official" Bob Ross look-a-like contest at Gallery Bar on Orchard Street.

“Now that we’re a little distanced from when he was alive, we have only begun to understand the significance of his unflappable joy,” said afro-wigged organizer Misha Calvert, referring to the bearded, big-haired star of the long-running PBS program The Joy of Painting, who died in 1995. “At the time, the Afro was in style, he blended in a bit more. Now that we’ve gotten so cynical as a country, someone like that stands out.”

Ms. Calvert organized the bash with online gallerist Alex Zoppa. “Alex Ross—Alex Zoppa—I keep calling him Alex Ross, like he’s related—has been sitting on [the idea] for years.” Now, she said, “it seemed like the perfect time to lift New York’s spirits.”

The Daily Transom asked contestant Joseph Brunetti, sporting a towering wig, how he took on the persona. “I sniffed a lot of paint,“ he said.

How did he view the competition? “I saw one woman with a real 'fro who I felt a real kinship to,” answered Mr. Brunetti, who daylights as a senior designer for Croc shoes. “I kind of wanted to touch her … with my brush.”

Upstairs, partygoers stood mesmerized at a projection of the late Ross’ show, watching as colors coalesced into a sky with scudding white clouds. Downstairs, a Bob Ross-certified artist demonstrated his methods, painting an idyllic snowcapped mountain over and over again as volunteers attempted to replicate it.  

“My roommate was trying to cheer me up,” said medical student Robel Beyene, 26, watching carefully before his turn at the easel, who remembers watching Ross’ show with his grandfather. “It completely works.”

“My parents were old hippies,” said Peter Edry, a 27-year-old insurance salesman. “There was a pungent smell in the air, and we would watch Bob Ross together.”

The night culminated in a performance by the Titanium White Hot Dancers, a mixed-gender troupe, who disco danced in curly brown wigs and denim shirts. The dance was choreographed by a member of a country western gay and lesbian dance troupe called the Manhattan Prairie Dogs, which recently performed a version of Beyonce’s “Put a Ring on it,” wearing skirts with tie-on bellies.

One onlooker summed up Mr. Ross' appeal thusly: “It used to be way kitschier, what he’d do,” said lawyer Carrie Trowbridge, 31. “But now, kitsch is cool, and maybe even subversive. That’s why this hip crowd is here."