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But why are the well-maintained daughters of privilege so attracted to this hard-living ex-hustler? Even Avalon is mystified by the throngs of budding socialites who scream his name and beg for kisses in the front row. We spoke on the phone while he was between takes for a magazine photo shoot. "I've known street hookers that are more sane and more level-headed than a lot of these debutantes," he says. But "maybe inside of themselves...they feel just as desperate and sleazy and disgusting." Insults only seem to incite them more. In his song "So rich, So pretty," Avalon raps, "I like a girl who eats and brings it up/A sassy little frassy with bulimia."
It's hard to imagine that these girls, with their Dior pumps and fresh manicures, could understand the hard-knock life that Avalon claims to have led. He spins a story of mythological proportions. His parents split up when he was young, and the burden of raising Avalon and his sister fell on his mother. She sold weed to get by, and when Avalon was older, she brought him into the business. His father was a chiropractor with a heroin problem who got busted for selling workers' compensation papers. "He was strung out most of my whole life, but he was real fun to be with," Avalon recalls. Avalon attributes his interest in music to the fact that he and his dad spent much of their time together listening to old blues and Tex-Mex records. His dad eventually sobered up and stayed clean for two years, although by then he was afflicted with both tuberculosis and hepatitis. In a cruel twist of fate, a drunk driver hit him as he was crossing the street after attending a Narcotics Anonymous meeting. Avalon, only 16 at the time, had to make the decision to take his dad off life support. "His mom—my grandma—she still doesn't know that I was the one who took him off."
Avalon's maternal grandparents were Holocaust survivors. "[They] were in the camps," he says. "But they weren't religious at all." Avalon, on the other hand, took an interest in Orthodox Judaism during his drug-using days. He grew a beard, he recalls, and convinced his then-fiancée to take conversion classes. They were living in Oregon at the time; Avalon flew back and forth to California, conducting large marijuana deals with his mother. Eventually, he says, his fiancée got pregnant and stopped getting high, but Avalon couldn't quit. "I thought when we had a kid I would just magically get sober and stay sober," he says. "But that didn't happen."
Their marriage didn't last long. Avalon moved to Portland, found a job at a bagel shop, and shacked up in a residential hotel. It was during that time that, as he says vaguely, "things got gnarly." His heroin habit worsened and it became difficult to find enough cash for a fix, so he hit the streets. "At first I would just go and rob tricks," Avalon explains. "Then the more fucked up you get, you don't have any strength really, where you can't pull a robbery, so I just was...I did compromising things." But, he's quick to add, "I never had to grab my ankles or do anything like that."