Winterland Shirt Designs 1989–1991
My first design job out of college was working for Winterland Productions in San Francisco. Winterland was founded by Bill Graham and specialized in merchandising the top acts in the music industry, responsible for some of the most recognizable concert and retail t-shirt designs of the 20th century.
Growing up in the Midwest and attending college in the South, I felt the strong pull of the West Coast. When I saw a story on MTV about the concert t-shirt industry and Winterland, I designed and mailed a crazy, postcard-size resume on the spot. A few weeks later they called: the Creative Director saw promise and offered me the day shift at $8 an hour if I moved out. I took it.
My first day of work landed on October 17, 1989, the day of the Loma Prieta earthquake. Two weeks later I was back at my dream job, designing t-shirts, posters, tour books, and pinback buttons from concept to final print-ready art, using a mix of digital and practical tools: colored pencil, paint, airbrush, photography, and photocopy. One of the best parts of the job was meeting with the bands and musicians themselves: LL Cool J, Soundgarden, Joe Satriani, Ian McCulloch, and New Kids on the Block among them, and working with clients like Levi's.
In 2025, I was flipping through the vintage tees at a shop in Guerneville, California, when I spotted it: a New Kids on the Block shirt I'd designed in 1989, priced at $48. It had been one of the biggest-selling shirts on the tour that year, and I'd received a $50 bonus for it. When I told the shop owner I'd designed it, he was shocked and thrilled. "You got to sign it!" he said. "Really?" I asked. "Absolutely. It'll be worth more." I laughed and obliged with an unrecognizable signature. It made my day.
Credits
John Caponi / Designer / Concept through final print-ready art on shirts, posters, tour books, and pinback buttons
