With his mahogany chest almost always on display in contrast to his luminescent grin, we thought we knew all of the intimate details we’ve ever really needed to know about Simon Cowell. 

But last week while appearing on a podcast, the showbiz bigwig fed fans another saucy titbit they probably weren’t expecting, and it was certainly a world away from Simon’s usual family-friendly form. 

Having been at the helm of some of the world’s biggest talent shows for over two decade, fans have always relished in the weird and wonderful world of the music mogul turned TV top dog. 

And after being almost killed by a sledgehammer on stage during BGT’s auditions in March, Simon, 65, has made it clear that he’s no stranger to getting stuck into the more unusual parts of his job. 

There’s no doubt that he’s thrown everything into his role as TV’s ‘bad guy’, and earlier this month he was rumoured to have amassed around £500 million – being named one of the richest people in the UK by Forbes Rich List in 2019. 

Renowned for signing some of the world’s most successful artists, from Five and Westlife to Olly Murs and One Direction, as well as helping to boost the profiles of co-stars such as Amanda Holden and Cheryl, it seems that whatever Simon touches turns to gold. 

Over the course of his career, which saw him start as a runner on the iconic ‘90s horror flick The Shining , Simon’s superpower hasn’t just extended to the could-be biggest names in the ‘biz, he’s also gone under the radar with signings like the Teletubbies, Power Rangers and puppets Zig and Zag. 

But it was in the world of talent shows that Simon really earned his stripes. Landing his role on Pop Idol in 2001, followed a year later by American Idol before founding his multi-million dollar entertainment company Syco in 2005. 

And last year marked twenty years since Simon created The X Factor, a talent show that trailblazed its way to the top and signed some of music’s biggest names, including Leona Lewis, Little Mix, One Direction and Alexandra Burke. 

Yet it hasn’t always been smooth sailing, with Simon enduring very public battles with the likes of Cheryl, Louis Walsh and Sharon Osbourne, who accused him of not knowing ‘how to keep friends’ when she and Louis appeared on Celebrity Big Brother last year. 

When appearing on the ‘How to Fail’ podcast last week, Simon was candid over his shyness, saying it was the ‘worst thing in the world’ to have to make small talk. 

His revelation would, perhaps, explain his latest confession that he had been forced to turn down a very cheeky from a couple who he had met during a night out. 

He told host Elizabeth Day last week, ‘One time -this is a true story -I was in a restaurant and this guy comes up to me and he said, ‘I love your show’. 

Simon went on to say he had replied, ‘Thank you very much’ before the man asked him for a picture and introduced him to his wife. 

Things then took an unexpected turn when Simon confessed how the couple had then asked him, ‘Would you judge us having sex?’  

After revealing how he had asked them if they were winding him up, Simon added, ‘They said, ‘No, we’ll pay you’…And it was actually a lot of money. And I thought, ‘Do I? No, I just can’t do it.’ It was $150,000.’

When it comes to his own romances, Simon hasn’t always been so shy. Famously holidaying on his luxury yacht or at his villa in Barbados with his ‘harem’ of ex-girlfriends, it was only when he welcomed his son Eric, now 10, with fiancé Lauren Silverman, that the famous ladies man finally settled down. 

Simon once admitted, ‘I’m attracted to crazy women. I encourage crazy behaviour and I make them crazy. I’m attracted to certain personalities who are difficult to control, so there are tantrums, tears, and fights, which is all part of the drama.

He added, ‘My life is really odd. Every girl wants to be number one and they’re very territorial. I like the fight because otherwise I’d have a dull group of girlfriends.’

Having dated ‘80s legend Sinitta on and off for 30 years, Simon went on to date Jackie St Clair, Terri Seymour, and Mezghan Hussainy, who he was also engaged to, before falling for Lauren. 

Tragically in 2020, Simon was nearly left paralysed and in a wheelchair for life after an accident on his electric bike left him with a broken back which required an 11 hour operation. 

And last week he candidly revealed how his priorities have shifted, and he now prioritises spending time with loved ones and enjoying his money over making more. 

Speaking on the podcast he said, ‘They said the obvious – it could go wrong – and all I could think about was my family and everything. In that moment you kind of realise the most important thing is your health and don’t do stupid things.’

He then went on to describe the billionaires he had mixed with as ‘obnoxious’ and ‘snobby’, saying about his fortune, ‘I’ve definitely got enough. I don’t need any more. I don’t yearn for what I thought I wanted a few years ago because when I was a kid I had no idea of anything like yachts, and the Caribbean, or private planes.”

And last weekend, Simon showed fans exactly how he likes to spend his time, sharing a series of snaps on social media of races in the swimming pool with his lookalike-son Eric, before the pair headed for a long dog walk with their German Shepherd. 

He captioned the snaps, ‘1. Love, 2. Even more love, 3. It was a long walk’.