Cannon was born in Boston, Massachusetts. He graduated from Grinnell College in 1995 with a B.A. in English.

His first professional comics work was The Chainsaw Vigilante, a spin-off from The Tick, from New England Comics. Beginning in the mid-1990s, he wrote and drew The Replacement God, a fantasy comic book about a former slave named Knute who is pursued across the fictional land of Mun by a tyrannical king and his beatnik Visigoth Death Horde. The first eight issues were published by Slave Labor Graphics, a subsequent five issues were published by Image Comics, and one issue was self-published by Cannon under his Handicraft Guild imprint.

Cannon worked as layout artist on Top 10, with writer Alan Moore and finishing artist Gene Ha, and pencilled its spin-off miniseries Smax, with Moore and inker Andrew Currie, for America's Best Comics.

In August 2004 Cannon co-founded Big Time Attic with former co-publisher Shad Petosky and fellow Grinnell College alumnus Kevin Cannon. With Big Time Attic, he has illustrated a book with Jim Ottaviani entitled Bone Sharps, Cowboys, and Thunder Lizards.

Comics work includes:

• Chainsaw Vigilante (art and script, 3-issue mini-series, New England Comics, 1993—1994)

• Bone Sharps, Cowboys, and Thunder Lizards (with Jim Ottaviani, G.T. Labs, 2005, ISBN 978-0-9660106-6-4)

Interviews

• The Big Time Attic interview at Comic Book Galaxy