Pictures of Kenny Rogers through the years show a man who truly lived life. The late country legend, who died March 20, 2020, was seemingly everyone’s friend — pop stars, athletes, actors … Rogers even palled around with the founder of Playboy!

Rogers, who died at the age of 81, had five kids from four of his five wives, including twins Justin and Jordan, now young adults. The children stayed out of the public eye for the most part, although we did manage to find a few then and now pictures of the boys from Wanda Miller Rogers’ Instagram.

Photos with celebrities including Michael Jackson, Hugh Hefner, Ray Charles, Johnny Carson and Glen Campbell fill this gallery, but you’ll meet three of Rogers’ wives along the way. Dolly Parton was his most famous country friend, and their bond held strong until his last days. Fittingly, she’s featured across this gallery of pictures that show the Gambler’s storied 50-year career.

After a farewell show in 2017, Rogers stepped away from the spotlight, although he wrapped up a few final tour dates in 2018. He’d planned to retire years earlier, telling Taste of Country he had no intention of returning in June 2016, months after his retirement announcement. Bad knees and poor health eventually did force him off the stage, and he lived the rest of his life at home in Georgia.

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