Craig was born in South Africa and later moved to Adelaide for a while with his parents. There he attended Semaphore Park Primary School.Later he moved to Bowral (located in the Southern Highlands), New South Wales and attended Bowral High School. Attending both of these schools makes him the only Chaser to be publically educated.
Craig attended the University of Sydney and graduated from Sydney Law School with Chaser colleagues Julian Morrow, Dominic Knight and Chas Licciardello.
In 2002-2003, he co-hosted TV show "CNNNN"
In 2004 and 2005 he and fellow Chaser member Chris Taylor hosted a radio drive-time show called "Today Today" on Triple J. In mid 2006 to early 2007 the two returned to a Sunday radio show called "Bloody Sunday".
In 2006 Craig returned to TV with the other Chasers for a show called "The Chaser's War On Everything"
The show returned in 2007 and is to return in 2009.
From 27 October to 5 November, Craig and fellow Chaser,Chris Taylor returned to Triple J for 8 days, in a weekday timeslot 5-5:30pm covering the US Election. The radio show was called "The Race Race".
In 2009, he will return for a third season of "The Chaser's War On Everything".