Taking to stand-up in 2001, Chris ended the year as a NSW State Finalist in the 'Melbourne International Comedy Festival/Triple J Raw Comedy' - the competition that 'unearths' fresh talent. As winner of the NSW final in 2003, Chris's National Final performance received a Special Mention at that year's Melbourne International Comedy Festival.
Despite Chris's best efforts while working in regional media, regional Australia had not yet attained fame for its comedy circuit. So in 2007 he returned to stand-up in Sydney, attaining a writing internship on The Side Show with Paul McDermott.