Madden began his career self-publishing minicomics in Ann Arbor, Michigan in the early 1990s. He was co-editor with Matt Feazell and Sean Bieri of the anthology 5 O'Clock Shadow. After several of his short pieces appeared in established publications, Madden's first graphic novel, Black Candy, was published by Black Eye Books in 1998.

In the mid-1990s Madden began writing reviews for The Comics Journal and other publications.

He works in illustration and comics coloring and also teaches comics storytelling at the School of Visual Arts. His graphic novel, Odds Off, was published by Highwater Books, and issue of his periodical series of short works, A Fine Mess, are published by Alternative Comics.

He regularly deals with themes in settings in Mexico (where he lived for a time in the late 1990s), or that are rooted in Mexican culture.

Madden currently lives in Brooklyn, New York with his wife, fellow comics creator Jessica Abel, and their daughter.