In 2002, Simon Cowell burst onto American television screens as the outlandish and very brutally honest American Idol judge. Flash forward to nearly two decades later and he has turned into a bit of a softie judging America’s Got Talent and Britain’s Got Talent. Whether you love him or love to hate him, Cowell’s life hasn’t always been full of riches and success. It has been marred by tragedy that he has had to overcome to shape him into the millionaire music mogul he is today.

1. Simon Cowell Dropped Out of School at 16

Cowell’s teenage years were full of getting into trouble at school. He was enrolled in Dover College in Kent, England when he was 14 years old. Cowell was anything but happy about attending this school away from his family. He felt like they were trying to get rid of him. From writing his parent’s angry notes to constantly getting suspended, he knew school wasn’t for him and decided to drop out at the age of 16.

As a teen, Cowell had a growing interest in the music industry. His father was a music executive at EMI Music Publishing and clearly the source of his inspiration. It was only a matter of time before he followed in his father’s footsteps and took a crack at breaking into the entertainment industry himself.

But Cowell couldn’t just walk right into the EMI Music Publishing office and ask for a job. First, he built up his resume by taking odd jobs. He got a job as a runner on the set of the 1980 film The Shining. After facing friction with his co-workers on set, Cowell left the job for good.

Finally, after tons of failed jobs didn’t work out for Cowell, he landed a job as a mailroom clerk at EMI Music Publishing. Here he realized how much power there is in networking and making connections with other people.

2. His First Music Label was a Bust

Cowell was able to get a position as a talent scout for an A&R executive at EMI. This provided him with a ton of hands-on experience and exposed him to a new side of the music industry. He felt it was finally time to leave the company and start one of his own with his business partner.

Unfortunately, his music company called E&S Music was a total bust. He returned to EMI as he planned his next move. Cowell started Fanfare Records in 1985 with his business partner Iain Burton. Sinitta was putting out hits under the label at the time which allowed them to have a few glory years. But in 1989, the company was facing financial ruin. The label was later sold to BMG.

Cowell was left incredibly close to being bankrupt and was forced to move back in with his parents. He got a job as a consultant for BMG Records where he set up his own label S Records. He was more determined than ever to find success. S records later became known as Syco Music, the label that has launched the careers of One Direction and Little Mix.

3. Simon Cowell’s Love Life has been Extremely Rocky

Now a father, Cowell has been notoriously known as a ladies’ man to the public for years. He has also kept in touch with some of his exes and still hangs out with him to this day. He was secretly engaged to Page 3 model Louise Payne in 1995. They broke off the engagement in 1998 because Cowell said he wasn’t ready to have children. He wasn’t ready to give up his bachelor lifestyle, which left Louise heartbroken.

Cowell was engaged once more in 2010 to makeup artist Mezghan Husainy. She struggled with jealousy and the fact that he was close to so many other women that he previously dated. His busy schedule jet-setting all over the world was another cause of concern for her as she felt like she never got to see him. They ended their engagement in 2012. He later revealed that this relationship was “a big mistake.”

Cowell has finally settled down with partner Lauren Silverman but this relationship didn’t come without controversy. She was still married to his friend Andrew at the time of their affair in 2013. The couple divorced after news of the affair broke and Lauren announced she was pregnant with Cowell’s child. The pair are now parents to 7-year-old Eric who has made several appearances on both America’s Got Talent and Britain’s Got Talent.

4. A Scary Electric Bike Accident Left Simon Cowell with a Broken Back

Just as Cowell was settling down with his family, another tragedy struck. He fell off his electric bike in the courtyard of his Malibu home in August 2020. After undergoing a six-hour surgery to repair the three broken vertebrae in his back and have a metal rod placed, Simon was on the road to recovery.

The accident could have killed him. The injury sidelined him from the live shows of both Britain’s Got Talent and America’s Got Talent for the remainder of both of the seasons. The 61-year-old underwent intense physical therapy and was up and walking again in a matter of weeks.

He will make his long-awaited television return when America’s Got Talent premieres on June 1.