Radio
Sandilands landed his first radio job with a Brisbane station by using a false resumé to impress one of the station's executives. In 1999, he moved to Sydney, and commenced at 2DayFM as host of the Hot30 Countdown, replacing "Ugly Phil O'Neil", a former husband of Henderson. Sandilands attributes his radio career taking off after being told by then Group Program Director Jeff Allis to 'do whatever you want, just win'..
Much media coverage of Sandilands has focused on the negative aspects of his personality and behaviour, notably his widely publicised clashes with and/or criticism of other media figures, his intemperate on-air outbursts and his alleged "out of control" ego. In September 2006, Sandilands was named the most hated Australian identity in a Zoo Weekly article, although on 14 October 2006, Sandilands and Henderson were named "Best On-Air Team" at the Australian Commercial Radio Awards.
In August 2009, The Kyle and Jackie O Show was put into "indefinite recess" by the Austereo network as a result of a controversial on-air stunt on his morning show on 29 July 2009. He returned to his radio show on 18 August 2009 but was suspended on 9 September 2009 due to on-air comments relating to Magda Szubanski. In the same year he was again named the most hated by Zoo Weekly. Sandilands and Henderson were the hosts of the nationally-syndicated chart show The Hot Hits, before swapping host roles with Andrew Günsberg in December 2009, who had previously hosted Take40 Australia, but is now being hosted by both Sandilands and Henderson.
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