There’s hasn’t been a more solid radio duo in Australia than Kyle Sandilands and Jackie ‘O’ Henderson.
The pair met in 1999 when Sandilands flew from Brisbane to Sydney to audition to replace 2Day FM Hot 30 host Phil O’Neil, who had moved to London, leaving Henderson, his then-wife and longtime co-host, behind.
They were big shoes to fill, and after some early nerves, Sandilands got the gig.
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Henderson, 51, recalled that time in her bestselling 2024 memoir The Whole Truth.
“Little did I know I had just been introduced to the man who would forever change my life and become one of my most trusted friends,” she wrote.
“His sheer brilliance and our divine chemistry together were about to make history by one day becoming Australia’s most successful radio show.
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“I would spend the next twenty-four years (and counting) of my life with this wonderful man, and if you’d told me that in that moment, I sure as hell wouldn’t have believed it.”
The pair would stay at 2Day FM, first on nights and then on breakfast, for 14 years, before moving to KIIS in 2014, where they remain under a 10-year $200m contract that takes them through to 2034.
It isn’t known if the contract includes an out clause if one or both parties decide to leave The Kyle & Jackie O Show.
This week, Henderson has been on leave from the show after an on-air incident on Friday, February 20.
The co-hosts got into a tense argument after Henderson took time out of a segment to read from Andrew Mountbatten-Windsor’s astrology birth chart. (The former royal’s star sign, for those who are interested, is Pisces.)
“Your fixation on this has made you almost unworkable,” Sandilands, 54, told his co-host live on air.
“You are off with the fairies with this s–t, it’s mental.”
Henderson said she was offended by her co-star’s comments, but he continued unabated, saying her fixation on astrology charts made her like a “drug addict”, knowing Henderson has faced addiction struggles in the past.
He also claimed it had started to affect her work, going so far as to say she didn’t know what was going on during some segments.
“You are not doing the rest of the job, and everyone in this building has mentioned it to me,” Sandilands said.
“Everyone has said, ‘What’s going on with Jackie? She’s off today.’
“You don’t know what the f–k is going on all the time, because you’re looking at that phone, playing in the stars, and it’s ridiculous.
“You can enjoy that, but you can’t take over your whole life.”
Listeners could hear Henderson becoming emotional during the exchange.
On Monday morning, Sandilands – who was off-air on a sick day on Thursday – announced his co-host would be taking a break from the show for the week.
While Henderson was well within her rights to take offense to the exchange, it could be argued Sandilands has made harsher comments to her over the years – but these incidents didn’t come close to breaking their solid union.
For some reason, this one tipped them over the edge, and for the first time in 27 years, their enduring friendship and working relationship seemed uncertain.
”A real country boy”
Reflecting on their first radio show together in her memoir, Henderson said it “did not go well” but by the second night, Sandilands “came on air and nailed everything”.
Henderson’s marriage to radio host O’Neil had ended after approximately six years and he left the show to move to London.
Henderson had just started dating her future husband Lee Henderson, with whom she would later welcome daughter Kitty, 14.
In her memoir, Henderson explained the key to their success was “marching in synch”.
“When I look back on any moments in our career when we’ve been disconnected, for one reason or another, the show was never as good,” she wrote.
“You can fake it enough to get by, but not enough to make things sing.
“When we’re aligned and having so much fun together, though, our rapport is as natural as it is unstoppable.”
She added that part of their magic was her ability to “take ribbing”.
“Kyle puts me down a bit, that’s our dynamic, but he also knew precisely how far to push things,” she said.
“I would push back, because I’m no pushover, but never with malice.”
Support on and off the air
The co-hosts had remained steadfast friends both on air and in real life, supporting each other through professional and personal highlights and struggles.
Sandilands was by Henderson’s side when she wed Lee in 2003, and Henderson attended Sandilands’ wedding to pop star Tamara Jaber in 2008.
They hosted the Top 30 on 2Day FM from 1999 until 2005 when they moved to the breakfast slot, rebranding to the Kyle & Jackie O Show.
Their later move from 2Day FM to KIIS was controversial, with Henderson sharing in the book that Sandilands made the decision without consulting her.
Henderson had conceived daughter Kitty in 2010 after several rounds of IVF. That same year, she and Sandilands had “become quite disconnected”.
“He had got divorced from Tamara and was struggling with the separation,” Henderson wrote in the book, adding Jaber was “a key plank in making Kyle’s and my partnership happen”.
She said the singer “created a lot of the connective tissue for us outside of work in those early years”.
After their split, Sandilands began to party hard, according to Henderson, who was focused on settling into life as a new mum.
During this time Henderson said her marriage was under strain and she began struggling with her weight, leading to Sandilands ribbing her for her weight struggles.
By 2004 they were back in sync and their ratings were consistently high, however there was some uncertainty over their future at 2Day FM as they approached their next contract negotiation.
“I remember that Kyle called me on Halloween,” Henderson recalled, adding her then-four-year-old daughter was “dressed up” and ready to go when Sandilands called her and said: “Darl, we’re going to Mix.”
ARN’s Mix would rebrand as KIIS and the Kyle & Jackie O Show would be their flagship.
“I couldn’t help but be mad at Kyle,” she wrote.
Thankfully, it all worked out in the end, and their were able to continue their ratings success at their new radio station.
With their professional success came yet another personal blow when Henderson and husband Lee divorced in 2018.
Personal and professional struggles
Both Sandilands and Henderson have experienced health and relationship struggles over the years, the most serious being Henderson’s battle with addiction in 2022 and Sandilands’ more recent brain aneurysm diagnosis in 2025.
Henderson chronicled her recovery from addiction to painkillers, sleeping pills and alcohol in The Whole Truth.
To seek treatment, she took a leave of absence from the radio show for the first time since taking maternity leave.
Henderson was absent for a month, travelling to The Betty Ford Centre in California, supported by her best friend and former Her Best Life podcast co-host Gemma O’Neill.
At the time, she didn’t tell Sandilands the real reason for her time away, instead saying she was “burnt out” and “unwell” and “in need of a break”.
By the time she returned to the Kyle & Jackie O show in 2023, she seemed happier and healthier than ever before and the duo continued to dominate the ratings.
Henderson returned in time to attend Sandilands’ wedding to Tegan Kynaston in 2023, and the couple chose her to be their son Otto’s godmother when he was born the year before.
Eventually Henderson began dating again and the Kyle & Jackie O Show felt renewed with the added colour of her dating stories.
Their ratings were strong enough for ARN to decide it was time for the pair to begin broadcasting the show in Sydney and Melbourne.
The show debuted in Melbourne in April 2024, but the pair’s magic touch failed for the first time.
Their unique combination of Sandilands’ bawdy ‘shock jock’ persona and Henderson’s sometimes strong yet often appeasing demeanor failed to land.
The future of the Kyle & Jackie O Show
The Kyle & Jackie O Show finished 2025 with a low five per cent share in Melbourne, compared to their dominant 12.7 per cent share in Sydney.
As of today, ARN is standing by the duo’s Melbourne expansion.
It remains to be seen how the pair will move on from this latest, and seemingly most serious, fallout to continue their Sydney dominance and build on their Melbourne results.
One thing is for sure, regardless: radio in Australia is unlikely to see a more successful and enduring paring as Sandilands and Henderson ever again.
And while Sandilands appears to be happy to continue in the role, Henderson may not be, if her other recent life choices are anything to go by.
In an unexpected move earlier this month, the presenter announced she would be leaving the Besties venture she launched with best friend and manager Gemma O’Neill, including her role as co-host of their Besties podcast Her Best Life, earlier this month.
She said the decision to step away has been part of a “big shift that has happened with me”, in reference to the inner work and self-examination she has been doing of late and sharing with their loyal followers.
This has included multiple conversations on the podcast about astrology.
“It does sadden me in many ways, because I have loved and gotten so much out of what we have done together and shared together here, moreso because we are able to share that with a community of people,” she said during her final episode.
“We get to talk about all the things that we have learnt and are passionate about and it’s been so fulfilling on many levels, and obviously being able to work with you, my best friend, has been so amazing.”
Henderson said she chose to step away due to a sentiment she began to share in one of the pair’s final episodes in 2025 – that she didn’t feel she could do the podcast because she “wanted to protect a fair bit of [her] private life”.
She did leave the door open for an occasional guest stint.
The launch of Besties, described as a lifestyle brand, was announced on July 18, 2023.
As part of the launch, Henderson and O’Neill hosted an event featuring Gwyneth Paltrow in October 2023.
Many saw it as Henderson’s attempt to build her own brand outside of the Kyle & Jackie O Show.
Now her time with Besties is over, it remains to be seen if this is the one major life change Henderson makes in 2026, or one of many.
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