In the days before Photoshop, four-color silkscreen was an unimaginably labor-intensive act of love. "I had the technical photographic knowledge, but I worked with wonderful artists--Chris Frayne [brother of George Frayne, aka Commander Cody], Greg Sobran, David Mann, Susan Taormina," he says, giving a tour of four decades of Ann Arbor T-shirt history: I Brake for Jake, No Nukes, Free John Sinclair concert (sold out long ago), Fleetwood Diner, WCBN 20th anniversary, and finally, "I Braked for Jake," printed for the beloved downtown character's funeral in 2007. Cleypool gave them away free to Jake's relatives: "I always thought Jake was a loner," he recalls. "Suddenly everyone was a relative. I didn't make any money on that."
Cleypool is not retiring, but he's moving to an office in the front of the 1832 Anson Brown building (the back, where he's been printing his shirts for more than twenty years, is a later addition) and focusing more on design. He has the contract for Ernest Hemingway T-shirts at the Hemingway Museum in Key West. Meanwhile, he's planning to sell what remains his historic collection at the Sunday Artisan Market in Kerrytown.
[Originally published in August, 2013.]