- During an audition, a female participant told Simon and the other judges that she quit her job at a hair salon so she can pursue her dreams on American Idol (2002); when getting rejected, Simon had asked for the phone and called the owner of the workplace where the rejected contestant got her job back.
- Was once a waiter in Elton John's restaurant in London.
- His father, Eric Cowell, was a record company executive with EMI. He died at home in 1999 of a massive heart attack on the very day that Simon got his first Number One with a then-unknown band called Westlife who his dad had predicted would become big.
- Became a father for the first time at age 54 when his girlfriend Lauren Silverman gave birth to their son Eric Cowell on February 14, 2014.
- Says that the first time he gave a criticism was at age four when he looked at his mother's white fuzzy pillbox hat and remarked "Mum, you look like a poodle" [Source: His book "I Don't Mean to Be Rude, But..."]
- Susan Boyle's star-making audition was one of Cowell's favourite moments on Britain's Got Talent (2009).
- Dropped out of high school at age 16.
- Has a problem with clowns.
- Has a neighbouring mansion, next to Elton John's, in Beverly Hills.
- When living in Elstree as a boy, he rubbed shoulders with Roger Moore, Gregory Peck, Robert Mitchum, Bette Davis and Maureen O'Hara. He even sat on Davis' knee while she learned her lines. Moore used to invite the Cowells to see the filming of The Saint (1962).
- Stanley Kubrick was his neighbour growing up. He pestered Eric Cowell, Simon's father, to sell his property to him.
- In 2007, Forbes magazine estimated his U.S. earnings at $45 million for the year.
- Is not planning to leave his son in his will because he wants him to make it on his own. (June 2017)
- He worked as a mail boy at EMI and eventually worked his way to become an A&R representative.
- Simon's father was of mostly Ashkenazi Jewish ancestry (Simon's paternal grandmother was born in Poland). The rest of Simon's ancestry is English, and distant Scottish.
- Turned down the chance to manage Take That, which went on to become one of the major boy bands of the 1990s.
- In 1990, he made his screen debut on the U.K. television series Sale of the Century (1989). His prize for winning: kitchen utensils.
- In 2011, a woman broke into his London home.
- A TV commercial proposal was made to him by his agent who told him that he would be paid $1m for a day's work (the good news). When Cowell asked about the bad news, he was informed that the commercial was for "Viagra". Cowell reneged (interview: Episode dated 5 April 2011 (2011)). (2010)
- Allergic to lambs' wool. Buys expensive cashmere jumpers.
- Got the U.K. No. 1 of the new millennium with Westlife.
- Has two nieces and a nephew: Tanyette Chantel (born October 18, 1981), Melissa Lee (born July 10, 1984), and Joshua Aaron (born April 15, 1986). All three of them have appeared in the audience during various first season episodes of Pop Idol (2001).
- Has said he finds Britney Spears to be fascinating and wants her to be a part of The X Factor (2011).
- Before becoming famous, Cowell held down several brief jobs; quantity surveyor, a job at Tesco (he never made it past the interview), trainee law clerk, a runner, a waiter, a job in the EMI mailroom, and an estate agency where he had his worst job ever as a canvasser.
- At age 30, he moved back with his parents after he lost everything he owned from various investments.
- Has three half-brothers, John Cowell, Michael Cowell and Tony Cowell, a half-sister, former child actress June Cowell, a biological sister, Lindsay Elizabeth Cowell and a younger brother, Nicholas Cowell.
- Ranked #6 in the 2008 Telegraph's list "the 100 most powerful people in British culture".
- In 2007, he earned an estimated $72 million in income from his various projects. $45 million from American Idol (2002), $15 million from Britain's Got Talent (2007) and The X Factor UK (2004), and $12 million from his record label.
- Donated £90,000 to the charity Friends of the Israel Defense Forces (FIDF). (2013)
- Has a waxwork figure in Madame Tussauds.
- His sister's husband is the cousin of pop star Robbie Williams.
- Good friends with Emma Noble. Friends with Mel B.
- He was awarded a Star on the Hollywood Walk of Fame for Television at 6801 Hollywood Boulevard in Hollywood, California on August 20, 2018.
- During auditions for The X Factor UK (2004), he made a bet with auditionee Paul Holt that he would pay him £50,000 if he got a #1 single. Holt was quickly signed by a record label - and backed by The X Factor UK (2004) judge Sharon Osbourne - to release "50 Grand for Christmas" in December 2004, which only charted at #35 in the United Kingdom.
- Best friends with his London neighbour Jackie St. Clair.
- In 1985, he co-founded Fanfare Records (UK).
- Publicly supported the Conservative Party in the 2010 General Election, and wrote an article for "The Sun" endorsing David Cameron as Prime Minister.
- Though he became famous as a singing judge, Cowell himself cannot sing or play any instrument. He does have a good ear for music and pitch though, which is what enables him to critique music and singing.
- The Sunday Times List estimated his net worth at $196 million. (2009)
- (May 10, 2010) Merited a place in Time magazine's - The 100 Most Influential People in the World ("Artists" category) - with a tribute provided by Nick Cannon.
- Put up £50,000 bail money for pop impresario Jonathan King when he was arrested in 2001.
- His former girlfriend is Terri Seymour. (2004)
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