Michael Kupperman is a comedy writer whose humor is notoriously surreal and absurd. His work often parodies other genres, including superhero comics. To this end, he has created numerous ridiculous superheroes such as the Mannister, a superhero who can turn into a bannister, and Underpants-On-His-Head Man, a normal man who fights crime wearing underpants on his head.

Kupperman's most famous characters are Snake 'n' Bacon, a snake and talking piece of bacon who appear in many of his works, including Snake 'n' Bacon's Cartoon Cabaret and Tales Designed to Thrizzle, an ongoing comic series. Snake 'n' Bacon have also appeared in a pilot on Adult Swim.

In addition to his comics, Kupperman has also created cartoons for Robert Smigel's TV Funhouse series.

In 2011, Fantagraphics Books published the book, Mark Twain's Autobiography 1910-2010, a collaboration between Mark Twain and Michael Kupperman, and follow-up to Twain's best-selling autobiography. Kupperman describes the first encounter with Twain: "'Here Mister Kupperman,' he said, thrusting a manuscript into my hands. 'Publish this, and let the world read of my adventures.'" The book combines prose pieces by Twain and comic images by Kupperman, recounting the past 100 years of Mark Twain's life. Thought to be long-since dead, according to Kupperman, Twain has been alive thanks to a wizard's spell, and has been going on adventures ever since.

Starting October 25th, 2011, Kupperman will be participating in a reading event with fellow historical satirist, Kate Beaton, at the Luna Lounge in Alphabet City in New York City. The event will occur monthly on the third Tuesday of each month.