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He had asked contestant Heather Cook, "Are you male or female?
" When Cook tried to make light of the question, Sandilands then made a joke about her weight, saying, "You're a belly full of laughs".
In 2010, he became a judge on Australia's Got Talent and also on Australia's version of The X Factor.
Sandilands has become known for controversial on-air stunts and offensive comments.
Sandilands attributes his radio career taking off to being told by then Group Program Director Jeff Allis to "do whatever you want, just win".
In May 2010, it was announced that Sandilands would become one of the new judges on the second season of The X Factor Australia, alongside other new judges Ronan Keating, Guy Sebastian and Natalie Imbruglia. In 2017, Sandilands narrated the reality television program Meet the Hockers, a show similar to Pawn Stars, which he also produced. on , and attracted very low ratings of just 98,000 viewers, being beaten by numerous other multichannel programs in the same timeslot.
Within weeks he had declared his willingness to do whatever it took to get ahead: to work anywhere, in any time slot.
He took gigs in Cairns, and then Darwin In 1999, he moved to Sydney, and commenced at 2Day FM as host of the Hot30 Countdown, replacing "Ugly Phil O'Neil", a former husband of Henderson (Jackie O).
In October 2005, he referred to the eventual 2005 Idol winner Kate De Araugo's arms as "tuckshop lady arms".
A year later, Sandilands referred to contestant Bobby Flynn as a "mong" – a derogatory slang term for mongoloid, referring to people suffering from Down syndrome.