Simon Cowell began his career as a record company assistant at EMI, thanks to his father’s help. After dropping out of school, he climbed the music industry ladder. Though he initially launched two unsuccessful labels, he didn’t give up. When things fell apart—he lost his home, his Porsche, and his independence—he found comfort in returning home. “I was quite happy, really,” he admitted.

Building an Empire
Cowell rebooted his career with S Records, signing acts like 5ive, Westlife, and Jerome, whose cover of “Unchained Melody” became a hit. Yet it was talent shows that truly skyrocketed his career. In 2001, Cowell and Simon Fuller launched Pop Idol, making Cowell an instant celebrity. The show’s success led to American Idol on Fox, where Cowell’s blunt critiques and catchphrase—”I don’t mean to be rude but…”—became iconic.

Breaking into America
The first American Idol finale, won by Kelly Clarkson, drew over 26 million viewers. Cowell saw an opportunity and released Idol-themed albums, generating massive profits. In just a few years, he became a multimillionaire. Shows like X Factor and America’s Got Talent only expanded his reach and income.