Simon Cowell | Career, Women, Family | Mansions, Luxury Cars & Dogs


Okay, I don’t mean to be rude, but it’s the image that many people have of a music executive, talent scout, and reality show judge Simon Cowell. 

Over the past two decades, Cowell has built a music media empire that has netted him hundreds of millions of dollars.

Check out how he accumulated has a massive amount of wealth and what he spends his millions on.


Cowell was born in London in 1959. His dad was a music executive, which gave young Simon inspiration for a career after leaving college early.

Indeed, after a stretch of odd jobs, which reportedly included working on the set of The Shining, among other things, Cowell got his job through his father at EMI Music Publishing, one of the largest recording conglomerates in the world.

Rise Through Music

The journey was not a smooth one by any means, as Cowell didn’t experience much success for a while. After nearly going bankrupt following the failure of his label in 1989, Cowell finally broke through in the mid-1990s, becoming a millionaire after the success of British duo Robison and Jerome, who he recruited and signed.

Judging Career

This led to his big break in 2001 when he earned a role as a judge on the British TV show Pop Idol. A year later he would move over to the American version, of course, called American Idol, which is where gained his most notoriety. 

Cowell would then use his fame to launch a production company, Syco, which subsequently began The X-Factor in 2004, which he also has judged on.

Not done yet, Cowell and his Syco founded America’s Got Talent in 2006, followed by the British version a year later.

The Got Talent format has spawned spinoffs in 69 different countries, making it the world’s most successful reality show, as recognized by Guinness World Records. While Cowell probably didn’t have much direct involvement in that achievement, it certainly helped earn him a lot of cash as the owner and brainchild of the brand.

One Direction

Perhaps the most notable discovery of Cowell’s career was in 2010 when a British boy band was mentored by Cowell during Season 7 of X-Factor. They finished third in the competition, but despite coming up short, Cowell was impressed enough that he signed them to his own Syco label anyway.

That band, of course, was One Direction. Cowell and his label also profited from successful show run from future breakout artists such as Fifth Harmony, among other successful international acts.

Women and Family

Unlike his career, his love life wasn’t the most successful for a long time. He dated British TV host Terri Seymour for several years in the 2000’s, but they ultimately split. That was followed by a brief engagement to make-up artist Mezhgan Hussainy over 2010 and 2011. 

All the while, he reportedly was dating American socialite Lauren Silverman, with the relationship allegedly beginning in secret in 2009, while Silverman was still married. 

In 2013, the couple was forced to disclose their relationship when Silverman became pregnant with Cowell’s child, which ultimately forced Silverman’s divorce. 

While it was a scandalous beginning, Cowell’s son Eric was born in 2014 and despite a few rumours to the contrary, the couple is still together.


Maybe his longtime love failures were the result of money being unable to buy happiness, but whatever the case, he can still buy a lot with the fortune he’s accumulated. 

After nearly going bankrupt at the age of 30, Cowell has more than made up for lost time, accumulating a net wealth that is currently estimated at $600 million. In a typical year, Cowell reportedly pulls in north of $50 million, with estimates for single years ranging as high as $95 million.

With that much dough, let’s see what he spends it all on.

Real Estate

Cowell has been a prolific owner of high-priced real estate, and his primary residence is certainly indicative of that.

He primarily lives in a mansion right off the Pacific Coast Highway in Malibu that he picked up for $24 million in 2017. The home, which was built in 1988, sits on a little over an acre and a half right on the coast and contains:

  • 6 bedrooms
  • 7 bathrooms
  • 8,600 square feet of living space
  • Venetian plaster walls
  • Fire fireplaces
  • Lighted tennis court
  • Koi pond
  • Two swimming pools
  • 4-car garage

The house is so spacious and luxurious that in 2019, the auditions for the celebrity edition of X-Factor were held inside his house! It’s one thing to invite a bunch of A-listers to your house for a party, but it’s completely different to televise it to the world!

That is far from his only expensive house purchase, though. He owns another mansion in Beverly Hills that he bought from Jennifer Lopez in 2005 for $12 million. However, living up to his reputation of being unhappy with things, he was not a fan of the design, so he proceeded to completely gut the house over a period of five years.

Once the dust settled, or I guess more accurately cleaned up by the contractors, Cowell had a 9,300-square foot mansion with six bedrooms, six bathrooms, floor-to-ceiling windows, an 8-car garage, a professional tanning salon and spa and a large backyard pool.

Still, on the West Coast, Cowell also purchased a home in Los Angeles’ Trousdale Estates in 2011 for $15.5 million that he also extensively renovated. That estate now sprawls out over 12,000 square feet and features 7 bedrooms, 13 bathrooms, and several fountains, among other features. He put the home on the market for $20 million in 2013, though there’s no indication he ever actually sold it.

With those three So Cal properties, he also has a $10.85 million penthouse in Manhattan near Central Park that he bought in 2014.

Rounding out his real estate empire, he has property across the pond in his native London, a seven-bedroom 18th-century mansion that he bought in 2018 for 15.25 million pounds, the equivalent of $19.5 million. 

Of course, because he can’t resist the urge, he requested permission to renovate the historic home and was just a few months ago was granted permission to add a nearly 50-foot long pool, pool house, and an upscale bar to the historic property. 

It appears that this may have been done as a precursor to spending more time there, as it has been reported that Cowell is wanting his young son Eric to attend school in London.


With so many properties, Simon Cowell needs a way to get between all of them, so naturally, he has an impressive fleet of high-dollar rides. 

He is reported to own at least 15 cars, with models including a Mitsubishi Evo race car, a restored 1932 Ford Model B, two Rolls Royce’s worth over half a million dollars each, two six-figure Bentley’s, two rare Jaguars, two Lamborghinis, and three Ferraris. 

He once owned a 2008 Bugatti Veyron that he rarely drove, to the point where he only put a reported 1,300 miles on the car in four years. The car, which with over 1,000 horsepower can reach a top speed of 254 MPH, is the fastest street-legal car in America After purchasing it in 2010 for $1.6 million, he auctioned it off in 2014 for a reported $1.25 million. 

What a life to have when you buy the fastest car in the nation and you can’t even find time to drive it! 

Having sold that Bugatti, his most expensive ride is now an AC Cobra MK IV vintage racecar that dates to the mid-’60s, which will run you about $900,000.

Recently, though, he swapped out one of his beloved Rolls Royce’s for a more environmentally-friendly Tesla Model X, which retails for about $119,000. For now, it appears that Tesla may be his daily driver at the moment.


With Cowell busy working on both sides of the Atlantic, he obviously can’t drive any of his massive car collection to all of his workplaces, so he’ll splurge on travel as well.

Also when I say he splurges on travel, he really spares no expense.

What exactly does that mean? Well, he owns a Gulfstream private jet that cost him an estimated $61.5 million. Various sources have reported that he only flies on his personal jet so that he can smoke while in transit.

Cowell is also known for his annual Christmas trips to Barbados. He is one of many celebrities who enjoys that Caribbean island in particular. In fact, he once used a $41 million mansion on the island for filming a semifinal round of X-Factor in 2010.

Furthermore, he enjoys the island so much that he has reportedly been exploring the idea of adding the exotic locale to his real estate profile, expressing interest in paying up to 10 million pounds for a property on Barbados. For those who don’t have the exchange rate memorized, that’s the equivalent of about $12.8 million. 


Like many of us, Simon Cowell has expressed an affinity for dogs, currently owning two Yorkshire Terriers, Squiddly and Diddly, as well as his late mother’s former dog, Freddie, and the latest addition, Daisy, who he found abandoned on his annual Barbados trip in 2018 and took home with him.

He even features an extensive photo gallery of his dogs on his website, which I have to say, that’s a first that I can think of. 

Last winter, he also donated a quarter-million dollars to K9 Friends, a dog charity in Barbados, who he also holds a benefit for each winter. 

All of that is certainly fine and dandy, though there’s one thing about his love for four-legged pups that’s definitely a little above and beyond. 

Last year, he told a British newspaper that he is ‘100 per cent’ cloning all of his dogs, at a reported cost of over $75,000 per dog. The process involves a South Korean company performing a skin biopsy on the dog’s stomach, then inserting the DNA from a skin cell into a harvested egg, and voila! a clone of a dog. 

Cowell said he wants the process to be done as soon as possible, so his dog herd may be doubling in size before too long. Good luck telling them apart, I guess.

Listen, I know a lot of people will do just about anything for their dog, but I haven’t met anyone who loves their dog enough to drop $75 grand to clone them, not yet at least.

If you had Simon Cowell’s crazy amount of cash, would you splurge for multiple multi-million-dollar mansions, a cool car collection, or a clone of your beloved pups? Let us know in the comments.


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