How a wayward boy became one of the most infamous voices on radio: Kyle Sandilands' life and career in photos
Updated . First published
Kyle Sandilands experienced a difficult childhood and even spent time living on the streets as a young man, so no one expected him to one day become the most infamous voice on Australian radio.
Here's how he went from driving a promotional car for a Townsville radio station to the biggest radio star in the business, and all the controversies – including the on-air blowup that's resulted in his $100 million ARN contract being sensationally torn up – he's faced along the way.
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Kyle Dalton Sandilands was born on June 10, 1971, and grew up with his parents and younger brother Chris in the coastal suburb of Wynnum, Brisbane.
Unfortunately his parents' marriage fell apart when he was young and they divorced when he was just 10, an event that would shape his formative years and leave a lasting impact.
"[Sandilands] used to listen to that Tammy Wynette song D-I-V-O-R-C-E and just cry and cry. He's never gotten over his parents' divorce," his aunt, Jill Stevens, told the Sydney Morning Herald once.
His mother remarried, but she and Sandilands' allegedly abusive stepfather kicked him out at age 15. The next few years he spent couch surfing and living on the streets before his he moved in with Stevens in Townsville when he was 17.
That's where he landed his first radio job.
After working a string of odd jobs (including at a meatworks, Cadbury, and an electronics store, where he was fired for stealing), Sandilands landed a gig at 4TO Townsville at age 21.
He got the job after supposedly showing an executive a fake resume claiming he'd worked at Triple M in Brisbane, but the job didn't actually involve him getting on the airwaves; he was instead hired to drive the station's promotional car around the city.
But Sandilands had his sights set much higher and worked at stations all over Queensland before snagging a job in Sydney in 1999, where he was paid $255,000 per year to host 2Day FM's Hot30 Countdown.
He was brought in to replace Phil O'Neil, who had been married to none other than Jackie 'O' Henderson, a woman who would go on to play a huge role in Sandilands' personal and professional life.
Henderson came on as Sandilands' Hot30 Countdown co-host in 2000 and the on-air chemistry and banter between the duo was electric, prompting 2Day FM to offer them their own show in 2004.
Thus, The Kyle and Jackie O Show was born.
Originally airing in the drive time slot, the show was hugely successful right off the bat and only grew more successful through the mid- to late-2000s, though Sandilands built a reputation for controversial commentary and wild on-air antics just as quickly.
In 2006, just two years into the show's on-air run, Sandilands was named the most hated public figure in Australia in a Zoo Weekly article and though he and Henderson racked up plenty of accolades for their radio show, Sandilands couldn't seem to avoid negative press.
One controversy in 2005 centred around singer Tamara Jaber, who just so happened to be Sandilands' girlfriend at the time.
Today Tonight accused the radio heavyweight of "cooking the charts" by giving extra air time to Jaber's song Ooh Ahh, an allegation Sandilands didn't appreciate one bit. He sued the program for defamation and won in 2006.
Jaber, who rose to fame when she won Popstars with her band Scandal'Us in 2001, had been dating Sandilands since she was 19 and stuck by him through the controversies in his early radio career.
The breakdown of Sandilands' first marriage came right after a string of high-profile controversies that saw him pulled off the air and fired from his first TV position.
In 2007, he called Molly Meldrum "arrogant", "fat" and "talentless" live on-air, then claimed he wanted to "punch Dave Hughes in the throat" during a TV interview for Enough Rope the very next month.
But the biggest scandal erupted in 2009, when The Kyle and Jackie O Show's regular 'lie detector' segment went terribly wrong.
During the segment, which involved a mother question her teenage daughter about her sexual history on live radio, the girl reported she had been raped at age 12 and claimed her mother was already aware of the abuse.
After a beat of silence, Sandilands uttered eight words: "Right... is that the only experience you've had?"
The stunt was cut short and Henderson apologised but the damage was already done.
Advertisers started withdrawing sponsorships almost immediately after the segment aired and a media circus erupted in the days that followed, with some Australians calling for Sandilands to be removed from his radio and TV roles.
He'd been with the Ten Network for several years by 2009, as a judge on Australian Idol and a co-host for Big Brother's final season with Henderson.
Almost a week after the lie detector segment went to air, Ten announced Sandilands had been sacked over concerns his continued presence on Australian Idol would damage the network's reputation.
Meanwhile, The Kyle and Jackie O Show was pulled off air a few days after the segment and didn't return until almost a month later - but it wasn't long before Sandilands was in hot water again.
Less than a month after returning to the airwaves, Sandilands was suspended for comments made about actress Magda Szubanski's weight live on air.
"You put her in a concentration camp and you watch the weight fall, like, she could be skinny," he said while suggesting weight-loss options for the star, who had been vocal about her body image struggles.
It wasn't the first (nor the last) time he sparked outrage by making fatphobic comments and he continued to cause controversy in the years that followed, regularly being called out for making sexist, ableist, homophobic, transphobic and other bigoted comments on live radio.
But the biggest headline for Sandilands in 2013 had nothing to do with his personal life.
At the end of the year, he and Henderson announced The Kyle and Jackie O Show - which had dominated the ratings for years by that stage - would be leaving 2Day FM and moving to rival station KIIS 106.5.
The show went to number one as soon as they started at the new station and Sandilands and Henderson were making millions, so things were looking good for the radio shock jock. At least for a while.
Sandilands wasn't single for long though; he'd already been linked to Tegan Kynaston, an office manager for his media company King Kyle, by the time he and Anthony confirmed their split.
Though they denied there was anything romantic between them at the time, the pair were officially an item the following year and in January 2022, Sandilands got down on one knee and proposed to Kynaston.
"We went to Port Douglas, went to the reef… and got engaged," Sandilands revealed on his KIIS radio show at the time.
"I'm very happy. I cried. I'm just an emotional type of guy these days. I have a fiancée. Can you believe it?"
Like his past partners, Kynaston is significantly younger than Sandilands and there's a 15-year age gap between them.
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