Defining ‘Ambitcheous’

Conventional dealers may well look askance at her work, some dismissing it as tasteless or garish. “It is art that certainly could polarize,” Mr. Bamberger acknowledged. But these days, he said, “when you buy a work of art, you buy into the person, the whole package, and Instagram is where the whole package plays out.”

It doesn’t hurt, either, that Ms. Longshore is relentlessly upbeat, “The word ‘don’t’ doesn’t enter her vocabulary,” Mr. Bamberger said.

It wasn’t always so. In Montgomery, Ala., where she grew up, “I was this weird kid who got picked on because I had a big voice and a loud personality,” Ms. Longshore recalled. But her mother had dreams for her, imagining Ashley at cotillion, fanning out her party dress and batting her eyes at the eligible boys.

“I was raised by the garden club, and my underwear had a monogram on it until I started my period,” Ms. Longshore said. “It would’ve been easier,” she writes in her memoir, “to dress pretty, fawn over those big-eared boys and learn my dance steps, but I couldn’t do it.”

She eventually decamped for Montana, where she taught herself to paint, and later New Orleans, a city she loves for its rawness. She peddled her earliest paintings — masturbating couples and the ribald like, to local galleries, and was mostly met with rejection. At night she sobbed, “crying snot bubbles,” she said. “I was let down by just being disrespected.”

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