"In cities like Manchester, with unemployment problems, there are no-alcohol venues where five thousand people under the age of sixteen are eccy'd off their heads every Saturday night.

The Doug Anthony All Stars were a singing comedy trio (comprising McDermott, Tim Ferguson and Richard Fidler) who began busking in Canberra in the 1980s and later gained notoriety at the Edinburgh Fringe Festival.

[citation needed] McDermott began busking in 1985, which he says equipped him with useful experience and the ability to cope with most situations when he later started performing in clubs.

[13] After initially struggling to gain success in Australia, in 1989 DAAS was picked up to perform on the ABC show The Big Gig, on which they became a popular feature.

Rumours of a falling out among the trio persisted for many years, but all three maintained that they had parted on good terms and that it had simply been time to move on, as they had wanted to pursue careers in different directions.

McDermott's monologues also broke new ground in Australian TV for their direct and harsh criticisms of prominent figures, especially politicians.

The ABC received a large number of complaints[citation needed] about McDermott for making light of tragic events, use of profanity and drug references, but his willingness to push boundaries was also the reason for his popularity.

This was one of the earliest panel comedy shows on Australian TV and was notable for ensuring gender balance as early as the mid 1990s.

[citation needed] In 1998, McDermott hosted a spin-off called Good News Weekend, which followed a similar format, but with questions based around pop culture.

The show was notable for introducing Australian TV audiences to a broad range of cabaret and circus acts while also featuring popular comedians and musicians.

[25] In 1996, McDermott was recruited by director Ted Robinson, with whom he had previously worked on The Big Gig, to host Good News Week, which aired on the ABC from 1996 to 1998, and on Network Ten from 1999 to 2000 and then returned in 2008 for a new series.

[26] McDermott opens each show with a humorous monologue based on the news on the week and is responsible for posing questions and awarding points to teams.

He had dreadlocks at the time, and was best known for the crude, aggressive "bad boy" character he had played in the Doug Anthony All Stars, which many tended to confuse with his actual personality.

In addition, it was doubted that he was capable of ad libbing and speaking well, as in past interviews he had usually allowed his fellow band members to do most of the talking.

"[28] He would regularly sing on the program, particularly on Good News Weekend and GNW Night Lite, including some of his own original songs.

[20] McDermott reunited with Robinson in 2007 when he was named host of a new ABC variety program, The Sideshow, a show described as a successor to The Big Gig.

[32] McDermott says he was saddened by The Sideshow's cancellation as he believed it was an excellent venue for performers of alternative work which would have achieved ratings success if it had been allowed to continue.

[citation needed] Following the end of Good News Week in 2000, McDermott returned to live comedy and music with a trio called GUD, which toured major Australian cities.

[citation needed] Their songs were mostly about topical issues and allowed McDermott to push boundaries further than he had been able to on TV by extensive use of profanity and mockery of tragic events.

The songs were interspersed with comedic material in which McDermott spoke about his experiences in the entertainment industry, reflections on global politics and banter with the audience.

He is interested in topical humour and targets issues about which he feels passionately, including the detainment of David Hicks, the AWB scandal, torture and the War on Terror.

[35] In 1995 he wrote, directed and performed in a stage show entitled MOSH!, which he says is based on "my drug-addled observations when I've been abusing substances".

received a range of responses; it won the award for best fringe show at the Adelaide festival and was described by one reviewer as "often hilarious", but was savaged by other critics as being "gratuitously offensive".

[36] The group uses topical humour in its music; their act includes songs about Osama bin Laden, the transportation of live animal stock and what they describe as contemporary Australian "folk heroes" such as Chopper Read, Rene Rivkin and convicted serial killer Ivan Milat.

[37] McDermott says that GUD is in a similar vein to the Doug Anthony All Stars in that it revolves around music, comedy and the inter-relationships between the band members onstage.

[39] In 2002, he also performed a solo stand-up show entitled Comedyoscopy, a deconstruction of comedy, comedic techniques and what makes people laugh.

[43] He has also written and illustrated three children's books, two of which (being The Scree and The Girl Who Swallowed Bees) have been adapted into short films with McDermott scripting, directing, performing and painting all of the animations.

"[48] He has also had small acting roles in several Australian films, including that of the band manager in The Night We Called It a Day and Trevor in the TV miniseries Through My Eyes: The Lindy Chamberlain Story.

[49] In 2020, it was reported that he would play the leading role in an upcoming miniseries, The Home Team, opposite actress, Tara Morice.