Indeed. With his trademark head rag—he has a seemingly endless supply in various shades and patterns—wraparound sunglasses, and carefully sculpted, graying facial hair, Orr looks more like a central casting biker than a man in search of a Stickley dining suite. Think Bruce Willis without the swagger or Mickey Rourke before the plastic surgery. Pickers, one imagines, would be slender, effeminate men and better-than-middle-aged housewives with an eye for Hummel figurines, not gruff, articulate, middle-aged dudes with a droopy goatee and a voice like gravel frying in brown butter.

The dealers Orr sells to aren't paying for appearances. They want his eye for rare stuff. "You can't buy what Rick has," according to Jonathan Wayne, who owns RED Modern Furniture in Phoenix and has bought from Orr for nearly 10 years. "You can't train people to know what he knows. He's an anomaly—a fair businessman with amazing knowledge about art and furniture."

It's knowledge Orr's refined over a lifetime of picking. He built his secondhand empire buying big-deal paintings for $5 and reselling them for thousands. He started as a kid, growing up in Hollywood in the '70s and raised by a mother Orr describes as "a hippie with little ambition." Dad was small-time movie actor Greg Benedict (you can see him in the 1963 Troy Donahue picture Palm Springs Weekend), whom Orr rarely saw.

Among Orr’s finds is this Anthony Palazzo painting (top right) belonging to Cleveland gallery owner Kenneth Lesko
courtesy of Kenneth Lesko
Among Orr’s finds is this Anthony Palazzo painting (top right) belonging to Cleveland gallery owner Kenneth Lesko
Cleveland gallery
owner Kenneth Lesko, who says eBay
“can’t replace the Rick Orrs of the art world.”
courtesy of Kenneth Lesko
Cleveland gallery owner Kenneth Lesko, who says eBay “can’t replace the Rick Orrs of the art world.”

"My stepbrother and I would go pester this old guy in our neighborhood named Junkman Jack," Orr recalls. "He'd go out picking, be gone for a week, and come home with these great stories and a truck full of stuff—Tiffany lamps and cool old furniture. He gave me a glimpse into a world most kids wouldn't care about."

Orr cared. Deeply. He dropped out of school at 15, scrounged up enough to buy a used truck, and became consumed with picking. Eventually, treasure-hunting took its toll on Orr's personal life. When he was married, he saw his wife only once a week; when he was home, he was on the phone brokering art deals. Time spent with his daughter Shannon usually involved camping out overnight in front of estate sales so Orr could be first in line when the house opened the next morning. Eventually, his wife left him.

He might have picked for a few more years, then moved on to something else—perhaps opened a gallery in Los Angeles or become a dealer himself—if he hadn't spotted "Three Wise Men" hanging over the mantel of a spec home in the desert north of Scottsdale where Orr had come to scrounge.

"The house was crammed with all kinds of sculpture and studio pottery and fine art," he remembers. "The sellers didn't know what they had, so everything was priced cheap. I turned the corner, and there was this Cubist painting of three figures. Lots of bright colors. It was beautiful, and it was priced at $500—more money than I had in the world at the time. I was paying for my stuff, and this lady walked up with the painting under her arm, handed the seller cash and left."

A few days later, leafing through a book on Spanish painters, Orr spotted a photo of the painting he'd just missed owning. "It was a Picasso," he says with quiet despair. "It got away from me, and I've been chasing it ever since."

The one about the valuable painting procured from a garage sale is an oft-told tale—and more often than not, it seems, the painting is one by Picasso. Last year, an early watercolor by the famed painter was found in an attic in Dorchester, Dorset, England. The year before, a Carolina Beach, North Carolina, couple bought a Picasso for a dollar at an estate sale. And just this past October, a Shreveport, Louisiana, woman paid $2 for a Picasso at a yard sale. "It just kind of caught my eye," she told a local news reporter. "It looks like a woman, holding a guitar or possibly a baby."

Orr doesn't begrudge these folks their yard-sale Picassos. "The guy was prolific," he says, laughing. "He paid bar tabs with paintings. And then there are the copies—good ones too. That one in Shreveport doesn't look right to me. I've seen fakes, but I'm not fooled. I keep right on going."

Orr is holding out for the real thing. It's a quest that once made him a very wealthy man—and, more recently, an extremely poor one.

"I have a decent head for business, but when things were going great, I lived large," he admits. "I'd drive by a Mercedes dealership and see a car I liked and go in and write a check. I drove a Rolls and a Bentley. I had homes here and in L.A. I had huge years where I could afford to live like that. I didn't know it would end. I figured, people will always die; they'll leave behind valuable stuff I can buy and resell. I thought I could always make good money."

He was apparently mistaken. Orr sold his last Mercedes, a G-500, in 2007; he needed the cash for picking. He lost his home, and he had to sell off his personal possessions as the Internet gobbled up his business, putting him and many other pickers mostly out to pasture.

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