Simon Cowell was reduced to tears after telling of how the biggest career moment in his life coincided with his most heartbreaking loss.

Simon Cowell spoke of his “desperately unhappy downward spiral” after suffering the loss of his “best friends” and strongest confidantes – his parents. Tragically just at the moment that the boyband he was managing, Westlife, made it to number one, his father died of a heart attack, meaning that he’d never live to hear the good news.

When the music mogul called his mum Julie from Germany to share that the group had become chart-toppers for the first time ever with Swear It Again, he immediately knew something life-changing had happened. Tears rising in his throat, he revealed: “I could just tell that something wasn’t right.”

Talking to The Diary of a CEO podcast host Stephen Bartlett of the “bittersweet” moment when success and grief collided, Simon confessed: “I genuinely at that point in my life just believed my parents were gonna live forever.” The choked-up singer continued: “At that moment, I’d have swapped everything I’d succeeded with to have kept him around.”

Simon added that, during his “amazing relationship” with dad Eric – whose name is now taken by his young son – he’d only fought with him on one occasion. “He only lost his temper with me once and when he lost it, I was like ‘I don’t wanna go there again’,” he recalled.

The Britain’s Got Talent judge continued that although his dad had never struck him in his life, “he raised his voice once to me and that was enough. When he was angry, you knew it!” Pausing for thought poignantly, he explained that he still spoke to his father in his head in the aftermath of his 1999 death, as his faith and belief in God gave him the feeling he was still present.

Simon broke down in tears as he pondered on his grief, while Stephen held a space for him, urging him to take his time.

After a moment of silence, he regained his composure, and started to talk about the death of his mum 16 years later, which had sent him on a terrifying “downward spiral”.

“Everything material meant nothing to me at that point. I was desperately unhappy,” he lamented.

He added that despite staying awake until 7:00 or 8:00am to get his work done, he “wasn’t particularly enjoying” his career at the time and was using it to fill a void.

“I became a ridiculous workaholic… I was very successful but I really, really wasn’t happy,” Simon explained.

He reflected on how his father might have felt about his success on TV talent shows such as X-Factor, where his notoriously withering comments towards contestants who didn’t make the grade earned him the nickname “Mr. Nasty”.

“I think he would’ve got a kick out of seeing me on a TV show and would have found the whole thing really, really funny,” he exclaimed.

“I maintained that amazing relationship with [my parents] right up until they passed away, they were my best friends… that’s how I feel about [my child] Eric now,” he concluded, describing their father-son bond as “pure love”.