[2] Simpson debuted as a comic book artist in 1984 with his creation Megaton Man, a Kitchen Sink Press title that sometimes satirized superheroes cliches.

Simpson wrote and drew the science-fiction backup feature Border Worlds, about a woman and a colonial rebellion, set on a space station, beginning in Megaton Man #6.

The feature spun off into a seven-issue, "mature readers" black-and-white comics (July 1986 – Aug. 1987),[4] followed by Border Worlds: Marooned #1 (April 1990), the only issue of an intended four-issue miniseries.

[11] In 1986 Simpson collaborated with Alan Moore on the comics short "In Pictopia" in Anything Goes!, an anthology published by Fantagraphics Books to raise money in the lawsuit brought by Michael Fleisher.

[3] Between 1990 and 1992, Simpson created six erotic underground comix under the pseudonym "Anton Drek," including Wendy Whitebread, Undercover Slut[15] and Forbidden Frankenstein.

Finnish translations of Wendy Whitebread, Undercover Slut and Forbidden Frankenstein appeared as Paula Patonki, Piilokyttänarttu[17] and Frankensteinin Perhekalleudet[18] respectively, issued by the Helsinki publisher Sötem in 1995.