A self-described loner growing up in a tiny village outside Nashville, Tennessee, Leon Dickey started drawing at age 8, he recalls, as “a way of going into myself and not being with people, because I was always changing schools constantly.”
Having never taken an art class, the famed painter and sculptor started his career as an illustrator after one of his many moves landed him in Michigan. But he didn’t have plans to stay in the state for long.
“The only thing I wanted to do was to be an adult and live in New York,” the Wyandotte resident says. “I didn’t want to live in the South. I didn’t want to live in the North. I wanted to live in NYC.”
He made the move in 1977 at 22, after convincing the owner of Haberdashery, a store in Birmingham where he worked creating illustrations, window displays, and merchandising materials, to open a second store on Madison Avenue.
Determining that the store needed to do some advertising, he suggested Interview magazine, which led to his going to the publication each month to submit the illustrations for the ads, and that’s where he first met Andy Warhol.
“[Andy] would be standing out on the corner of Madison Avenue and 66th Street with a stack of Interviews, handing them out to people,” Dickey recalls. “That’s how the magazine really was.”
One day, Dickey was feeling nervous about a full-page ad he was illustrating for a New York shop called Illuvatar that was going into Vogue. He went to Warhol for advice, concerned that others were far better illustrators than he was.
“I said, ‘What am I going to do?’ Andy said, ‘Copy it, trace it, just make it happen.’ He said, ‘Just do whatever you have to do to make it happen.’ And so I did.”
Dickey found friendship with famed fashion icons as well, including journalist and Vogue editor-at-large Hamish Bowles, jeweler Vicki Sarge, and milliner Stephen Jones.
“All those friends from all those years ago are still in my life,” he says.
Moving professionally from illustrator to painter, Dickey received a contract with an up-and-coming gallery in the East Village, which he says in the late ’70s was coming to life with the likes of Keith Haring, Kenny Scharf, and Jean-Michel Basquiat. But when his contract expired, despite the fact that he had found success and exhibited at The Metropolitan Museum of Art, he decided New York was too expensive and moved back to Tennessee to get a “real job.”
veneer sculpture.” // Photograph by Sal Rodriguez
That only lasted a couple of months, until he got a phone call from an old friend suggesting he come back to Michigan to rent a former ice cream factory in Southgate and turn it into a discount alternative clothing store they named Penny Pincher. The store became renowned throughout metro Detroit.
“People say to me, ‘I still got that jacket. I still got those shoes. I still got that handbag.’ The shop itself was an art project.”
And when they decided to sell the building about 20 years later, Dickey met fashion icon Linda Dresner, who offered him an artist-in-residence opportunity in her Birmingham store, which started a deep friendship between the two. He continued to exhibit there until she closed the boutique in 2021.
“I thought that that was a high bar because I admired her so,” he remembers of Dresner, who also had a boutique on New York City’s Park Avenue that was frequented by such customers as Jacqueline Kennedy Onassis. “We were collaborative. She used to hang clothes on my sculptures, and they worked great.”
This story originally appeared in the September 2025 issue of Hour Detroit magazine. To read more, pick up a copy of Hour Detroit at a local retail outlet. Click here to get our digital edition.
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