Until 2001, Wills was active in the Christchurch entertainment scene, appearing at balls, private functions and corporate events; running weekly comedy nights and appearing on local television. In 2002, he moved to Auckland to become a resident comedian at the casino in SkyCity Auckland, where he had a weekly show, the "NCB Comedy Hour", blending circus and vaudeville styles. In 2008, Wills took his show "The Boy With Tape On His Face" to the Melbourne Comedy Festival, where it received critical acclaim. After Melbourne, he moved to London, appearing as a modern mime and wearing the traditional striped shirt.