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“If you're a man, you don't have to worry about your manliness.” Sometimes, all you need is a few famous friends to make it as a notable name in Hollywood, which is exactly what happened with Los Angeles native David Gest. A close personal friend of the late Michael Jackson since the age of 10, Gest’s friendship with the King of Pop certainly boosted his career when Jackson hired him to produce the Michael Jackson: 30th Anniversary Celebration: The Solo Years television special in 2001. A year later, Jackson upped the ante when he played matchmaker and introduced Gest to actress and singer, Liza Minnelli. Within months, Gest and Minnelli were married only to separate in 2003.

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Amid making headlines for his high profile friendship with Jackson and his four-year divorce proceedings with Minnelli, Gest proved he had something else in common with Jackson—a love of plastic surgery. Desperate to rekindle his fame after the loss of Jackson in 2009, Gest didn’t think twice about joining the cast of Celebrity Big Brother in the United Kingdom in 2016 where, despite leaving after 13 days due to illness, he had plenty of time to dish a few details about his life. Among those details, Gest was loose-lipped about Jackson’s encouragement for him to get plastic surgery for the first time in 1980. “I did my eyes and I had a facelift when I was very young,” he said, “because Michael Jackson said to me ‘You’ve got to make yourself always look better.’”

Acknowledging that he went under the knife for more than one rhinoplasty to enhance his nose alongside Jackson over the years, Gest is one of the few celebrities to candidly admit his regret for ever opting for plastic surgery. During his short stint on Celebrity Big Brother, Gest said, “I thought to myself, ‘Oh, I’ll do this because Michael told me.’ What an idiot I was. I’m telling people be who you are, you do not need to do plastic surgery. It’s the stupidest thing in the world.”

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With neither Gest nor Jackson ever resembling their younger years after first meeting as children, the friends were obviously on an endless search to perfect their looks and used plastic surgery to bond. Who knew friendship could blossom over Botox, brow lifts, facelifts and more? Literally leaving nothing untouched as we know from Jackson’s transformation, Gest even opted for a hair transplant in 1990, but it wasn’t until his friend passed away in 2009 that he finally learned to embrace his look and found the confidence to return to the spotlight.

As for Gest’s tumultuous relationship with Minnelli, the couple married in a lavish ceremony in 2002 but separated a year later as tabloids uncovered the growing tension and dysfunctional nature of their home life. Over their four-year divorce proceedings, Gest talked a lot about his marriage and even sued Minnelli over accusations of abuse, which was later thrown out in court. He also shocked Minnelli and her lawyers by detailing their marriage (as well as his early life) in his memoir, Simply the Gest, which he published after the divorce was finally settled in 2007.

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Essentially in hiding during his marriage, Gest rekindled his courage and further embraced his looks after the divorce and made his return to reality television on shows like I’m a Celebrity…Get Me Out of Here in addition to appearing as a guest judge on Soapstar Superstar and Grease Is the Word. “It is the best thing I ever did,” Gest said. “I finally realized that people like me. I guess people saw the real me and I realized I wasn’t just a freak in sunglasses.”

Although he acknowledges Jackson’s strong influence over the majority of his $30,000-worth of procedures, Gest admits that it wasn’t all Jackson’s idea. “It was my idea to put in a cleft chin and cheek bones—not Michael’s. Sometimes when you are young, you are foolish and you get carried away. I remember when I was looking in the mirror in an office building…I was mortified and almost fainted. I had the cheekbones removed a week later. I’ve come to realize that it’s not what’s on the outside, but it’s what’s on the inside that counts.”

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Sadly, Gest’s realization came much too late in life as the 62-year-old suffered a stroke on April 12, 2016 and was later found dead in his room at the Four Seasons Hotel in East London. Friends and others close to Gest admitted that the former producer was still mourning the loss of his beloved friend and, after giving up on plastic surgery, had turned to gambling to drown his sorrows. Learning the hard way that his luck wasn’t at the poker table or at the slot machines, Gest racked up hundreds of thousands of dollars in debt, blowing a large chunk of his $50 million net worth.