Find Out Why Simon Cowell Is Still Unmarried and How Much He Is Worth

The name Simon Cowell will continue to ring a bell even long after he is gone; there are two main reasons for this, one is for his objectivity in his discharging his job as a judge in several talent hunt/reality shows and the second would be for remaining true to himself. The world has witnessed Simon’s bluntness as well as his soft part armed with the ability to discover, train, and promote talents around the world of entertainment.

Cowell is popular for the series of international talent hunt platforms like X-Factor, America’s Got Talent among others. He is a producer, entrepreneur, Founder, and Chief executive of the British Entertainment Company, ‘Syco.’ His efforts on TV have not only made him popular but extremely wealthy piquing the interest of many in his journey to the top.

How Simon Cowell Made His First Million

With the kind of fame he has attained, not many are aware that Cowell had one of the humblest beginnings in the world of entertainment. As a young man looking to build a career, Cowell struggled with keeping several menial jobs, as a result, his father who was working as an executive at EMI Music Publishing company at the time got him a job in the mailroom. Dissatisfied, Simon Cowell left EMI but returned again after failed attempts on other jobs.

In the 1980s he set up his own company and went into music production. Coupled with the rises and falls that came along, Cowell started marking his success in the music industry in the 1990s. Luck shone on him in 1995 when he convinced Jerome Flynn and Robson Green to record “Unchained Melody.” The song did not only top the chart but also earned him his first million. Later on, he signed stars like Five, Westlife, and Teletubbies.

Growing His Wealth With Talent Shows 

Simon presently has a net worth of about $600 million. From the time he made his first million, he has consistently grown and increased his net worth. His peak salary as a judge on Pop Idol, later renamed American Idol was $33 million.

After featuring in the first series of the U.K.’s Pop Idol, Cowell established a music and television company called Syco Entertainment and as founder, he created The X Factor in the U.K., in the USA, as well as Britain’s Got Talent, and its U.S version America’s Got Talent. Between June 2017 and June 2019, Cowell, per Forbes’ calculations earned $96 million.

Syco Entertainment has sold over 200 million albums worldwide and boasts of over 180 hit singles. In 2004 and 2010, Cowell was named as one of Times 100 most influential people in the world.

He’s Got An Impressive Real Estate Portfolio

Simon Cowell
Cowell’s Malibu Home image source

Cowell also invests in real estate. He is well known for buying and selling luxury properties in London and L.A while reserving some for himself. In 2017 he paid $27 million for a 10,000-square-foot Malibu beachfront property in addition to his Beverly Hill and London homes.

The Malibu property is a beach house with stunning sea views. The exotic piece of luxury has seven bedrooms, nine bathrooms, a tennis court, a swimming pool, spa, a guest suite with its own entrance, and staff quarters.

In early 2019, he acquired yet another mansion in the Wimbledon neighborhood for a whopping $15 million. This is where he currently stays with his partner Lauren Silverman and son. He reportedly acquired the property so that his son could be closer to his school.

Cowell’s Adultery With His Best Friend’s Wife

It is no news that Simon Cowell is a lady’s man and has dated so many women. He made the news on a negative note when word got out that of all the women in the world, he chose to date his best friend’s wife, Lauren Silverman.

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Lauren became famous when her relationship with Simon was made public. She was introduced to Simon by her husband Andrew Silverman during a trip in 2006.

Andrew and Lauren would later part ways on the grounds of adultery with Simon Cowell’s name mentioned. In 2013, her relationship with Simon was uncovered when her pregnancy was confirmed. She is the mother of Simon’s son Eric who they welcomed in February 2014.

Simon, his partner Lauren and son Eric (Image Source)

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Though Simon and Lauren are yet to tie the knot, sources have revealed that he has gifted his best friend’s ex-wife an engagement ring, though it is said that the gift was not accompanied by the usual question.

Before his relationship with Lauren Silverman produced a son, Simon Cowell has publicly and severely insisted on never getting married, notwithstanding, fans thought that his relationship with Lauren would change that but the strong-willed TV personality has stayed true to his word.

Cowell is still not ready for marital commitment and his reason is simple, he can’t bear the idea of ‘losing his freedom’. There have been lots of rumors and speculations that the couple had gone their separate ways but Cowell’s spokesman debunked the rumors reassuring fans that the couple is currently having the time of their lives and are happy as a couple.

Meet The Women That Simon Previously Dated

The showbiz mogul has dated a handful of women in the past; he does have an eye for beautiful women, here is a look at some of them.


Simon Cowell was attracted to one of the famous models of the 1980s. According to the gorgeous model, she lost her virginity to Simon at age 16. They were childhood sweethearts, growing together in Hertfordshire and had known each other since age 12.


In the mid-1980s, he dated Jackie St Claire, a page 3 glamor model in the UK Tabloid newspaper who is specialized in photographic calendars and lingerie Cafe lounges. In 1988, she made an appearance in Hugh Hefner’s popular lad’s, ‘Mag Playboy’. They have since remained close.


Sinitta is Cowell’s most famous ex. She was a singing sensation in the ’80s who everyone can remember. After months of being together, she dumped him when she accepted an offer from David Essex. The So Macho hitmaker remains close to Cowell despite their relationship ending years ago. On numerous occasions, she appears in X-Factor during the judges’ house stage.


According to Day Star, Simon Cowell secretly engaged Page 3 Model Louise Page. He is said to have approached her first after spotting her at a Swanky London Shindig after he was completely smitten by her personality. Their relationship ended because they both wanted different things; it is recorded that she wanted kids and he wasn’t ready.


Simon had a thing for Page 3 girls… Georgina was a page 3 girl and a lap dancer. The gorgeous blonde said that she met Simon at a Spearmint Rhino Club where she worked occasionally but this was before Pop Idol, and he wasn’t famous. They saw regularly for six months but it wasn’t official. At an interview with The Sun, Simon said; “She’s a great girl. We find an awful lot to laugh about, but she’ll never be a Pop Idol. If you’ve heard her sing in the shower you’ll know what I mean. But she has tremendous talents in other areas.”

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If Simon could have many short relationships, surprisingly he could keep long relationships. Simon’s relationship with Terri was for 7 years (2001-2005). Terri Seymour is a presenter. Their relationship ended after she dumped Simon and as usual, Simon is still in talking terms with her to date.

Chuck Dez
Chuck is a personal finance and entertainment writer with over 15 years of experience covering famous biographies, personal finance, celebrity net worth, and celebrity lifestyles. He loves the process of researching new information, discovering and learning new things, as well as putting into words, interesting things others might like to read. When he's not talking about the future of media, business or entertainment, you'll find him watching films, reading or spending time with his wife and kids


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