His career started in 1985 when he was part of a group called Gigantic Fly, they performed mostly for small audiences in clubs and pubs, it was at this time when he met Richard Fidler and Tim Ferguson both part of the musical comedy group The Doug Anthony All Stars (DAAS). He joined the group when Robert Piper left to focus on personal projects. In 1989 the group performed on the show “The Big Gig” becoming regular performers.
His versatile career has lead him to pursue writing, becoming a published author and a columnist for Australian Newspapers like The Sydney Morning Herald, The Age, The Weekend Australian and The Sun-Herald. A book named “The Forgetting of Wisdom” was published, this material was a compilation of all his best columns. He also published two children storybooks called “The Scree” and “The Girl who swallowed bees”, McDermott not only illustrated these books he also turned them into short films developing the creative direction of the films directing, scripting and painting all the animations displayed in them.
Director Ted Robinson (The big Gig) hired him in 1996 to host “Good News Week”, this program was transmitted for two years for ABC Network. In 2002 McDermott hosted the AFI Awards and the television show “Strictly Dancing” for ABC (2004-2005).
In 2007 he reunited with Ted Robinson in the programed “The sideshow”, McDermott build a big audience for this show, but a combination of poor programming and low rating the show got cancelled after twenty-six episodes.
He was nominated for a Gold Logie Award in 2010 for Most Popular Personality on Australian Television. In 2015 he made a comeback to television by hosting “Room 101”.