Simon had his first kiss when he was nine and lost his virginity eight years later.
Since then, he’s slept with 100 or so women by his best guess. “I based my estimate on when I lost my virginity, figured that it was roughly 25 years ago and guessed that I had slept with an average of three to four women a year,” he explains.
Simon turned out to be a less reliable boyfriend than producer. According to Sinitta, he not only cheated on her three times, he made passes at her sister and her best friend and is “incapable of being faithful.”
Simon was once approached by a man who said he would pay six figures to have Cowell judge him and his wife in bed. He refused—which he says he regrets.
When in London, Cowell meets with his mother, Julie, a retired ballet dancer, for lunch twice a week. In 2005, he spent $500,000 on her surprise 80th birthday party.
Simon was suspended from boarding school for four months after being caught drinking—something he started doing at the age of nine, the same age he started smoking. He dropped out of school at 16.
Cowell now smokes Kools and says, like a proper control freak, “I’ve a golden rule, which is to drink only in the evening. I’m never drunk.” (I TOLD YOU SO!)
Cowell has produced 25 number one singles and has sold more than 60 million records.
He sports veneers. (I TOLD YOU SO!)
He owns no less than 30 black Armani T-shirts.
Despite his allegiance to the designer, he’s been abused in Britain for wearing extremely high-waisted trousers—and has taken to untucking his shirts as a result.
The one luxury item he’d take to the island? A mirror, “because I’d miss me.”
American Idol was turned down by every network before getting picked up by Fox—only because Elizabeth Murdoch told her father Rupert it was good.
Supposedly 5′9″, he sports shoes with a enormous heels.
If he could invite anyone, living or dead, to a dinner party, he would have Sinatra, Bill Clinton, and Natalie Wood.
