[citation needed] In 1989, Dickson joined Sony Music UK (then CBS Records) as a press officer, managing Public Enemy, LL Cool J, Midnight Oil, Warrant and Michael Bolton.

In 1990, he moved to the Epic Records label as a marketing executive working with Pearl Jam, Ozzy Osbourne, Living Colour, Screaming Trees and Celine Dion.

He became Director of International for Sony UK in 1993, overseeing global strategies for all Epic and S2 label artists, including Jamiroquai, Des'ree, Reef, Manic Street Preachers and Basia.

He moved to A&M Records UK in 1994 as Director of International, looking after acts such as Chris De Burgh, Therapy, Del Amitri, The Bluetones and the Mowax label, including DJ Shadow, Money Mark and U.N.C.L.E.

[3] In 2001, he moved to Sydney to take up the position of General Manager of Marketing for Sony BMG Australia, and remained in the role until August 2004.

Viewers initially disliked him for his insensitive, cold attitude (including controversial comments on a female contestant's weight), but towards the end of his tenure he became popular for his candid assessments of performances based on his expertise and experience within the record industry.

[citation needed] His first role at the Seven Network in 2005 was as host of the second season of reality TV series My Restaurant Rules, succeeding Curtis Stone.

[citation needed] During this time, Dickson and his business partner and manager, David Wilson, formed Watercooler Media, an independent television production company.

On 30 November 2006, The Sydney Morning Herald reported that Dickson would return to Network Ten in 2007 to become a fourth judge on the fifth season of Australian Idol, rejoining Mark Holden, Marcia Hines and his successor Kyle Sandilands.

[citation needed] In January 2008, it was announced that Dickson would be hosting the breakfast radio show on Vega 91.5 alongside comedian Dave O'Neil and former Big Brother runner-up Chrissie Swan, replacing Denise Scott and Shaun Micallef.

He and his business partner and manager, David Wilson, developed the show, in which celebrities were required to answer yes or no before a live studio audience to tricky moral questions such as, "Is it wrong to tell your kids there is no God?"

In July 2015, Dickson played Widow Twanky in Bonnie Lythgoe's stage production of Aladdin and his Wondrous Lamp at the State Theatre in Sydney, Australia.

Starting on 29 November 2016, Dickson appeared in the second season of the TV series First Contact on SBS, one of six well known Australians spending twenty-eight days living in various Indigenous communities across Australia.

It was Cowell who convinced Dickson to take the role as the "villain judge", despite his reservations given that he was relatively new to his adopted homeland and wanted to settle at a gradual pace.

On an episode of the ABC Australian news program Four Corners broadcast on 19 February 2007, Dickson discussed his problems with alcohol.