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In 1969 Kitchen decided to self-publish his comics and cartoons in the magazine Mom’s Homemade Comics, inspired in part by Bijou Funnies and Zap Comix. The selling out of the 4000 print run inspired him further, and in 1970 he founded Kitchen Sink Press (initially as an artists’ cooperative) and launched the underground newspaper The Bugle-American, with Jim Mitchell and others. Under the name of the Krupp Syndicate, he syndicated comic strips to almost 50 other underground and college newspapers. In addition to the Milwaukee artists like himself, Mitchell, Bruce Walthers, Don Glassford and Wendel Pugh, Kitchen began to publish works by such cartoonists as Howard Cruse, Robert Crumb, Art Spiegelman, Justin Green, Trina Robbins, and S. Clay Wilson, and he soon expanded his operations, launching Krupp Comic Works, a parent organization into which he placed ownership of Kitchen Sink Press and through which he also launched such diverse ventures as a record company and a commercial art studio. In 1980 he invited Cruse to edit Gay Comix, one of the first comics to feature the work of openly gay and lesbian cartoonists.
In the 1980s through the early 1990s, Kitchen Sink Press would publish industry legends such as Will Eisner, Harvey Kurtzman, Al Capp, and award-winning alternative creators such as Mark Schultz, Monte Beauchamp, and Charles Burns.
In 1993, Kitchen Sink Press merged with Kevin Eastman’s Tundra Publishing and relocated to Northampton, Massachusetts. It would go on to publish works by Alan Moore, Neil Gaiman, James O’Barr, Don Simpson, and Scott McCloud, winning numerous Eisner and Harvey Awards.