In 1998, Kelly graduated from the Minneapolis College of Art and Design where he studied under comic book artist Peter Gross.
[2] He worked with Gross on the DC Comics series Lucifer and The Books of Magic, both under the Vertigo imprint.
[3] From 2000 to 2007, he was part of the MCAD staff, teaching classes on Comic Book creation and illustration.
[4][5] In 2004, he illustrated the political satire Giant Robot Warriors He illustrated the entire twelve issue run of the Oni Press comics series Local, written by Brian Wood, a story arc ("The Cross + the Hammer") for Wood's Northlanders, and the DC/Vertigo ongoing series Saucer Country by Paul Cornell.
He has produced illustrations for Time Magazine and Rolling Stone.