Woodley made his solo debut in 2003 at the Melbourne International Comedy Festival with "The Happy Dickwit", a show about "a whole lot of unrelated ideas". He has since performed a number of solo stand-up shows, and in 2008 debuted a one-man play entitled "Possessed". Directed by Kate Denborough and featuring music from Paul Mac, "Possessed" is the story of Louie, a lonely recluse who falls in love with, and becomes possessed by, the ghost of a 19th-century shipwreck victim. Woodley says that the show came out of the desire to do a big solo show and his interest in doing a romantic comedy: "So I was thinking that maybe I could do a solo romantic comedy where I fell in love with myself. Although it was just a stupid joke initially, I started thinking about having a ghost possess me and then I fall in love with the ghost. I have to help free her from the curse she's under." The show has toured both nationally and internationally, and draws inspiration from Buster Keaton, Charlie Chaplin, Don Adams, Peter Sellers, Jerry Lewis and Laurel and Hardy.