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.