Kyle Sandilands: Overcoming hardship to become Australia’s radio icon
Kyle Sandilands currently dominates the airwaves with his shock jock bravado and controversial antics.
But take a glimpse into his childhood and you’ll understand why he is the man he is today.
Growing up in a broken home, Sandilands moved around multiple times and attended more than 10 different primary schools. The trauma of his parents’ divorce at age 10 left him scarred and made him focus on his career rather than family and children.
And this week, Sandilands revealed yet another obstacle that’s been thrown his way: he needs to undergo surgery for a potentially deadly brain aneurysm.
Watch the video above.
READ MORE: Bedtime habit you don’t realise is ruining your sleep
”On Friday, I was told by my medical team, which sounds like I’m already very sick, to have a medical team, that I have a brain aneurysm and it requires immediate attention, brain surgery,” the 53-year-old radio star told listeners during The Kyle and Jackie O Show on Monday morning.
“They can either do keyhole surgery, or they’ll have to cut away parts of my skull and open up my head to fix it,” he said.
Sandilands said he would need up to eight weeks off the air.
For a daily dose of 9Honey, subscribe to our newsletter here
Kyle shares sweet pic from day with son Otto
It’s not the first obstacle Sandilands has been forced to overcome, though after his $1 million wedding to the mother of his child, Tegan Kynaston, in April 2023, it seemed he’d finally found his happily ever after.
Let’s take a look back at the life and times of Kyle Sandilands.
Tough childhood
Sandilands has made no secret of the fact he had a dysfunctional, “intense” childhood in Brisbane after his parents’ split.
READ MORE: The truth about the ‘5am club’ – is it all it’s cracked up to be?
He and his brother went to live with their mum but were forced to move around a lot. This meant Sandilands attended 13 primary schools in his youth.
“I was always the kid in the wrong school uniform always trying to assimilate, so that’s pretty much when I became the class clown,” he said in an interview aired on comedian Ahn Do’s Brush With Fame back in 2016.
On the program, the KIIS FM host revealed his mother, Pam, eventually remarried and his stepdad’s “old-school discipline” made his childhood even more difficult.
“He’d pull the belt out, but I didn’t mind because I didn’t mind taking the heat because I’d seen my mum take the heat for many years,” Sandilands told the comedian.
READ MORE: She’s the child of a Hollywood hero but there’s one place she’s more famous than him
“So as long as she was happy and she was safe, then I thought this was normal family life.”
However, the household became so strict, said Sandilands, that he moved out at age 15 and was essentially homeless on the streets of Brisbane like a “real street rat”.
Sandilands recalled living behind a supermarket as well as a horse float at a petrol station. It was here fell in love with radio as he listened to night-time broadcasters over the speakers.
“Every morning there would be crates of bread delivered, crates of milk in the loading dock out the back, so I’d take a loaf of bread and a carton of milk and eat that dry bread,” he recalled of living behind the supermarket.
“Still to this day I’ll guzzle milk out the carton and take three or four slices of dry bread and munch on that.”
READ MORE: One thing one of music’s biggest names won’t show her fans
Sandilands was grateful to an auntie who eventually took him in from the streets and took him to Townsville to live with her.
Rise in radio
“I don’t know what you’re planning on, Sandilands, but there’s no job out there where being a smart-arse makes you money,” were words said to him by one of his teachers.
But the hurtful comment did little to deter the budding broadcaster.
He spent 10 years in radio promotions in Queensland until he scored a full-time gig on breakfast radio in Sydney. He relocated interstate and was soon hired by 2Day FM to host the Hot 30 Countdown with Jackie ‘O’ Henderson for a reported $255,000 a year.
READ MORE: It was the photo fans itched for – now it leaves a bad taste in their mouths
Both Sandilands and Henderson have since defected to KIIS FM, where they broadcast The Kyle & Jackie O Show in Sydney and Melbourne on a historic 10-year deal reportedly worth $200 million.
“If I could really live it over again I’d change nothing because all roads lead to this,” Sandilands told Anh Do.
“[My] general humour on air or off air is a bit blue and a bit crude. That’s just what I find funny, so I can understand that some people think I’m an a–hole.
“I don’t find knock-knock jokes funny, I find something that’s a bit naughty funny.
“I think people that listen to the show regularly, that listen a lot, realise I’m not a bad person.”
READ MORE: Four letters revealed their ‘feud’ had ended – but it was too late
Sandilands may now be the king of radio, with his reported $10 million annual salary, but he said he’ll never forget where he came from.
“I never have any money stress but I have that feeling deep in my gut or deep in me somewhere is living back in that cardboard box,” he said in a previous interview. “I think that’s what drives me.”
Love and marriage
Sandilands has had a number of long-term relationships over the years. In a 60 Minutes interview in 2020, he revealed his quest to be loved.
FOLLOW US ON WHATSAPP HERE: Stay across all the latest in celebrity, lifestyle and opinion via our WhatsApp channel. No comments, no algorithm and nobody can see your private details.
New details from Kyle Sandilands and Tegan Kynaston wedding
“I’m the kid who was thrown in the gutter at 15… I’m always looking for someone to love me back. I’ve got a lot to give but, you know, I want it back. Probably more than I want to give,” he told his mate, journalist and Today co-host Karl Stefanovic.
When Sandilands made the brief pivot from radio to TV in 2001 to be a judge on the singing competition Popstars, little did he know he would meet his future wife, Tamara Jaber – she would go on to win the competition with her band Scandal’Us.
The couple began dating shortly after the reality TV show was filmed.
In 2008, after seven years together, they were married at St Brigid’s Church in Sydney’s Marrickville, before hosting a lavish $1 million reception at the Doltone House in Pyrmont.
READ MORE: One topic you’re banned from ever asking superstar about
Sandilands later revealed on air that Jaber tried to call off their wedding the night before the ceremony because she felt he was “making a mockery” of the event by giving away tickets to their nuptials on his radio program.
“When I was married, my wife told me the morning before we got married – she was only my girlfriend then – ‘I think we’re making the biggest mistake of our life getting married tomorrow,”‘ he told co-host Henderson, who was a bridesmaid at the wedding.
“And I was like, ‘No, don’t be silly. Everyone’s here.’ And I thought these were just pre-wedding jitters. But no, she really didn’t want to.”
READ MORE: He was our next action hero. A split second on set derailed everything
Two years later, in 2010, the couple announced their split.
One decade later, in a frank on-air discussion about his split, Sandilands owned his part in the demise of his marriage, saying he often becomes emotionally distant in relationships.
“That’s what I do. I think I shut down quietly as time goes on. And then you just drift apart, drift in different directions,” he confessed.
“I probably didn’t pay much attention to the other half back then. I was younger, I was driven mainly by work and I was like, ‘Oh yeah, I’ve got a girlfriend, got a wife. Ticked that box, move on.'”
READ MORE: Two-word label young superstar is being forced to defend herself against
And he was quick to move on from Jaber. In 2011, while his divorce was being finalised, he was already dating Imogen Anthony, an American model he had met at his 40th birthday party, who was 20 years his junior.
Sandilands and Anthony went on to date for eight years before they parted ways in November 2019. The shock jock announced the split on air, telling listeners: “We haven’t been with each other for quite a few months now. Unfortunately, it’s run its course.”
And then there was Tegan Kynaston…
One month after his split from Anthony, Sandilands was rumoured to be dating his then-personal assistant, Tegan Kynaston, who is 15 years his junior.
Inside Kyle Sandilands and Tegan Kynaston’s lavish honeymoon
The pair initially denied the romance but made it Instagram-official when Kynaston shared a photo of herself kissing Sandilands on the cheek on New Year’s Eve 2019.
In January 2022, Sandilands proposed to Kynaston during their luxury holiday to Port Douglas. Weeks later, they announced they were expecting their first baby together.
“I’m having a baby!” he said on The Kyle & Jackie O Show while confirming the baby was due that August.
READ MORE: ‘Humiliating and hurtful’ video plagued singer for years
Otto Sandilands was born in August 2022, with his father and mother tying the knot in April 2023.
The radio star and Kynaston wed at Swifts, a $60 million heritage-listed Gothic Revival mansion at Sydney’s Darling Point.
The “royal wedding” was held on the anniversary of Prince William and Kate Middleton’s 2011 wedding, and cost Sandilands an estimated $1 million, which included a $75,000 catering bill.
READ MORE: Phone plans that promise to be a ‘budget game-changer’
Sandilands and Kynaston’s 130 guests included Prime Minister Anthony Albanese and New South Wales Premier Chris Minns.
Speaking on KIIS 1065 after the wedding, Henderson said: “It was beautiful, very beautiful. The chapel was stunning, Tegan looked incredible, incredible! And it was just very emotional.”
Months later in August 2023, baby Otto celebrated his first birthday with a party worth $25,000.
Inside Kyle Sandilands’ son Otto’s $25K first birthday party
His exclusive birthday bash wasn’t the first or last expensive treatment he got.
”My child’s already a millionaire,” Sandilands claimed on air in September 2023.
“He’s already got $1 million in his bank. Not even one. Otto’s already been loaded up by his great-grandfather.”
If you or someone you know is impacted by sexual assault, domestic or family violence, call 1800RESPECT on 1800 737 732 or visit their website. In an emergency, call 000.
