Woodward considered either a career as a rock musician or artist. He ultimately chose the latter and moved to Los Angeles, where he spent some years experimenting with his artistic style. He subsequently followed the example of one of his idols, David Bowie, and moved to Germany, where he went into self-publishing, producing a comic book composed of his expressionist paintings called Flesh Angels. He followed this up with an anthology comedic series called These Things Happen.

He then relocated to Desert Hot Springs, California, where he collaborated with A. David Lewis on the independent comic book Mortal Coils, and with Michael Colbert on the Digital Webbing Presents series Crazy Mary, for which he continues to do covers. Crazy Mary was noticed by IDW Publishing, which offered him the job of illustrating a CSI: NY miniseries. He subsequently illustrated a story in Boom! Studios’ Zombie Tales. When Peter David moved his series, Fallen Angel to IDW, Woodward was chosen as the regular artist.

His painted work eventually caught the attention of Marvel editor, Mike Marts, who hired him to illustrate X-Men Origins: The Beast, which was released September 2008.