When it comes to TV talent shows, Simon Cowell is renowned for being brutally honest and for discovering some of the world’s most successful pop acts, such as One Direction and Westlife. While fans might feel they have a pretty solid handle on Cowell’s personality, thanks to his appearances on the likes of American Idol, The X Factor, and America’s Got Talent, there’s actually lot more to the music mogul than meets the eye.
People might be less aware of what Cowell is like behind the scenes, from what his home life is really like to the worst mistake he’s ever made. Prior to becoming the iconic talent judge we all know and love (or, you know, love to hate) today, the English-born television personality started his career in an unexpected place and underwent several major setbacks along the way. Here we take a look at some of the lesser known facts about how Simon Cowell became the successful businessman he is today.
Simon Cowell started out in a record company’s mail room
Born in London in 1959, Simon Cowell was introduced to the music industry at an early age by his parents. In 2014, the Financial Times revealed, « Cowell’s father Eric was not wealthy but had a good income, becoming the head of property for EMI, The Beatles’ label. » Cowell confirmed his dad’s inspiring career to the publication and said, « It was a very cool British company so he was proud to work for them. There was something special about it then. »
After dropping out of school and forgoing college, Cowell « floated in and out of jobs, sabotaging several interviews set up by his father, » before he finally secured a job with EMI, albeit in the mail room (via Biography). Meanwhile, Hello! claimed that it was actually Cowell’s mother who helped him land the gig after she « saw an ad for a job in EMI’s mail room and filled in an application for him. » However, in an interview with Extra in 2018, Cowell revealed how he hoped his son, Eric, would one day follow in his footsteps. « I would do what my dad did, » the star said. « I would have him start as intern, learn the job. »
Basically, Cowell appears to have used his start in the mail room to his advantage before going on to build an incredible career in the music industry.
He almost went bankrupt in the ’80s
Simon Cowell’s net worth might be seriously impressive these days at an estimated $600 million, but that wasn’t always the case. Before developing his successful career, he underwent several financial hardships. While speaking to the Daily Mail in 2012, the media mogul explained, « I was a typical ’80s cliché. I had the cars, the house, the image and everything was beyond my means. I spent too much time at parties and then everything imploded. » Living the high life came at a price and Cowell ended up losing almost everything. « I’ve had many failures, » he explained to the publication, the biggest being, « my record company going bust. »
While many might have assumed that Cowell’s rise to power was smooth, it turns out that he had to learn some difficult lessons along the way. Several publications suggest that the celebrity went bankrupt, and according to Cowell himself, he came incredibly close. « I got rid of everything — I had negative equity on my house, » he continued. « Losing everything is probably the greatest lesson you learn. I went back to my parents’ house and started again. »
Losing his business and moving back in with mom and dad is not exactly the career beginning that multimillionaire Cowell exudes now, but it definitely makes his journey much more relatable.
Simon Cowell regrets having an affair
While Simon Cowell has been happily linked to his partner, Lauren Silverman, for years, their public romance didn’t get off to the easiest start: News of their affair first broke in 2013, when it revealed that Silverman was pregnant with Cowell’s child. Us Weekly reports that the relationship allegedly started in 2009, when Silverman was still married to one of Cowell’s close friends. In an interview with the Mirror in 2014, the former American Idol judge admitted, « I regret that part. » But according to the music mogul, the benefits ended up outweighing the negatives: « You have a baby and you look at the baby and you kinda go ‘this is what happened from it.' » Silverman and Cowell welcomed son Eric that February.
According to Cowell, his affair with Silverman was a wake up call that forced him to grow up. « It is not something I am proud of or wanted to happen in terms of hurting anyone, » he told the publication. As for how the celeb managed the difficult situation, he explained, « You have to deal with it and man up to it. You have to accept the responsibility and the criticism. » It seems that Silverman and Cowell have continued to make their relationship work, despite the complicated way it apparently began. While giving advice to anyone finding themselves in a similar situation, Cowell offered, « Deal with it a day at a time and own up to your responsibilities. »
This star vacations with … his ex-girlfriends?
Simon Cowell may be in a committed relationship with Lauren Silverman, but that hasn’t stopped the couple from vacationing with some of his ex-girlfriends. Yep, Cowell has remained close with several of his former loves, including pop star Sinitta (pictured, left) and TV presenter Terri Seymour.
In January 2014, the New York Post reported that Cowell had taken Silverman on a babymoon trip before the birth of their first child — but it may not have been much of a romantic trip with Sinitta and Seymour tagging along. Citing Cowell’s pals, the publication suggested, « Silverman doesn’t like Sinitta but she has come to accept that her flamboyant presence in [Cowell’s] life is non-negotiable. » Three years later, Cowell, Silverman, and Seymour vacationed together again in Los Cabos, Mexico.
Sure, Cowell’s friendships with his exes may be unusual, but it looks as though the music executive makes it work, jokingly telling Access in 2017, « That’s how I roll. » And while Sinitta previously « pronounced him incapable of fidelity » in a 2003 televised documentary (via GQ), Cowell’s enduring relationship with Silverman seems to suggest that the star has finally met his match … even if he does still spend a lot of time with his exes.
Simon Cowell wanted to call in sick to American Idol
Being a judge on American Idol might seem like the best job, but Simon Cowell apparently wasn’t always enamored with the experience. Of course, he famously quit the singing competition series in 2010 to launch The X Factor, but before that, Cowell had to approach his role on Idol just like any other job. In 2011, he told GQ, « I had a deal with Fox, and you’ve got to do what you’ve been paid to do. » But according to the publication, appearing on the TV show soon became an albatross for Cowell and « the kind of tiresome obligation he’d always told himself to avoid. »
Revealing the absolute dread his role on the series started to fill him with, Cowell told GQ, « There were times I used to wake up and I knew it was an audition day, » describing it as « the same feelings I used to get Sunday nights at school. » Hey, who hasn’t experienced that feeling in the pit of their stomach at some point during their life or career? « I used to wake up and think, I just wish I could do what I used to do — put a cup of tea on my head and pretend I’d got a fever, » Cowell admitted. In case you needed any further explanation as to why he eventually quit the job, Cowell told Hollywood Life in 2019, « I found the word ‘Idol’ obnoxious to be honest with you. »
He watches cartoons instead of the morning news
While it’s unclear if this music magnate’s routine has changed much after welcoming son Eric, GQ reported in 2011 that, « Each morning — as he breakfasts, has his morning bath, and prepares for the workday ahead — Cowell watches cartoons. » Explaining to the publication why he chose to do this, Simon Cowell revealed, « It just puts me in a good mood. » He continued, « It’s less depressing than watching the news, which is just relentless. You’ve got to try it one morning. You’ll be happy for the rest of the day. » Hey, he’s got a point. Apparently, Cowell’s cartoons of choice usually hail from Hanna-Barbera, with particular favorites being classics like The Flintstones and The Jetsons, which is understandable.
GQ was also quick to note that Cowell takes his love of cartoons so seriously that he « travels with backup DVDs, just in case. » While one might assume that the TV star needs to be up on current affairs in order to do a good job of capturing the zeitgeist in his many talent show roles, Cowell has proven otherwise. Maybe we should all take a leaf out of Cowell’s book and watch cartoons to start off the day.
Simon Cowell has overcome his fear of needles
Simon Cowell is an extremely busy person and, as a result, he tries to keep himself in great shape. After all, with regular appearances on multiple TV shows, he can’t afford to get ill. In an enlightening interview with GQ in 2011, Cowell revealed that he has a secret weapon when it comes to staying healthy, and it involves « an intravenous drip with B12, magnesium, vitamin C, and, he says, ‘something for your liver.' » The once « scared of needles » Cowell gets hooked up to a drip on a weekly basis, which he fits into his schedule whether he’s at home or at work. As the talent judge explained, « Even when I’m having a viewing session with producers … she just sticks a needle in me and we carry on doing whatever we’re doing. »
The IV drip sessions only take approximately 30 minutes at a time, and as Cowell told GQ, he feels the difference almost instantly. Singing the drip’s praises, Cowell said, « When you have it done, it’s an incredibly warm feeling. » And that’s not all. The music executive even claimed, « You feel all the vitamins going through you. It’s indescribable but very calming, and then it gives you energy for a good few days afterwards. » Where can we sign up?
He’s got a penchant for horror flicks
Anyone who’s ever been terrified of this judge will be able to believe that he once worked in horror. In 2009, Simon’s half-brother, Tony Cowell, gave an interview to BBC 3 (via The Telegraph), in which he revealed that the entertainer worked on the classic movie, The Shining. Per Tony, « He did plenty of menial jobs in those days and he even worked as a runner on The Shining, » which just about explains how Simon developed such a scary TV demeanor. Tony continued, « I well remember him saying he used to clean Jack Nicholson’s axe in between takes for the most famous scenes. » He also claimed, « He took great pride in it, you could see your face in it, it was so shiny. » As for what his brother is up to now, Tony joked, « The only thing he shines these days are his teeth. »
Simon also had a cameo in Scary Movie 3, a role he’s less than enthralled about in hindsight. Appearing in the horror parody might have seemed like a good idea at the time, but Simon told Entertainment Weekly in 2009, « I’ll never forget going to that premiere and dying in my seat when the movie came on. I’ve never felt so embarrassed in my life. Lesson learned: Don’t believe that you’re good at other things. I might be okay as a judge, but I’m a lousy actor. » Guess he should’ve stuck to cleaning axes.
Cowell could’ve been the face of Viagra
Believe it or not, but Simon Cowell could’ve been the face of Viagra. In a 2008 interview with Glamour UK, Cowell said (via the New York Post), « Last year my agent rang me and said, ‘You’ve been offered an incredibly big, million-pound deal. It’s to be the face of Viagra.' » But rather than being thrilled about the potentially huge financial incentive, the talent show judge was offended. Cowell revealed to the publication, « I just said, ‘Sorry, but that has to be a f**king insult.' »
Meanwhile, Cowell was later forced to defend a 2019 Barclaycard ad set in the Antarctic that he chose to star in. Speaking to the Daily Mail, he said, « I don’t normally do adverts, but this one appealed because it was an interesting message, and done in a fun way. » The talent show judge drew major criticism for starring in the ad as, according to campaigners, some of the company’s actions have allegedly increased the impact on climate change. While Cowell described filming the advert as « fun, » we can’t help but wondering what the star’s Viagra commercial might have looked like. And considering all of his other career successes, it’s sure to have only benefited the brand immensely.
Simon Cowell credits his weight loss to veganism
When Simon Cowell debuted his new look in 2019, rumors began to fly regarding how he’d achieved his 20-pound weight loss. According to the Daily Mail, Cowell told Best magazine, « People have said: ‘Oh, he’s had a gastric band fitted’ — but I haven’t. If I had, I would admit to it. » Instead, the businessman credits veganism with his new look, revealing that he’s overhauled both his diet and his lifestyle. « I met this doctor in LA and he told me my diet was appalling and I had to cut out fatty foods and certain drinks, » Cowell told the magazine. « The first few weeks were difficult, but then I actually stopped craving sugar. »
As for his biggest struggle when it came to cutting out everything from red meat to gluten to dairy, Cowell opened up and said, « The hardest part is when I see Eric eat pizza in front of me. That’s really tough. » (This is beyond understandable.) Cowell also told Access Hollywood that his memory has improved as a result of the diet, which is how he found it so easy to stick to. Plus, he revealed that the fact he « can still drink beer, » when it’s gluten free anyway, is a real bonus.