Huddleston started working in comics in the mid-1990s at the age of 21, doing creator-owned projects for Spoon Ink and Caliber, as well as some work for DC Comics, including a short run on Deathstroke with Marv Wolfman up until the title's cancellation.

[1] Huddleston returned in 2000 with the creator-owned The Coffin for Oni Press, written by Phil Hester.

Since then, Huddleston worked for independent publishers, Marvel and DC Comics, as well as latter's Vertigo and Wildstorm imprints, including lengthy runs on Harley Quinn with A. J. Lieberman and Gen13 with Scott Beatty and creator-owned mini-series such as Mnemovore with Ray Fawkes and Hans Rodionoff and Deep Sleeper, again with Phil Hester.

His latest assignment was Butcher Baker, the Righteous Maker, a creator-owned project at Image with Joe Casey on writing duties.

Huddleston responded to Casey's public statement by stating that the delay was caused by his need to take other work in order to make sufficient money, as Butcher Baker was not lucrative enough for him to avoid doing so.