This shirt dates to 1982.
Quoting from "PunkFunkRockPop," by Patty Dean, in Minnesota History,
The Quarterly of the Minnesota Historical Society, Spring 2002:
The new club [Upper Deck] commissioned Matt Feazell, an aspiring comic-book author and employee at nearby Shinder's bookstore, to produce a cartoon for a t-shirt. Some of the figures are Minnesota musicians who played regularly at Goofy's. Leading the charge is Curtiss A (rock and roller extraordinaire, renowned as the "dean of scream"); close behind is a bespectacled Pat Woods of Man Sized Action, wielding a microphone stand. The Hüsker Dü trio of Bob Mould playing his signature "Flying V" guitar, Greg Norton clutching his bass, and long-haired drummer Grant Hart brandishing drumsticks wear t-shirts with the band's logo.
Can you figure out who is the guy standing behind the Hüskers?