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In 2004, Rogers and his fifth wife, Wanda, welcomed twin boys Jordan and Justin in July — just a month before his 66th birthday. "They say that twins at my age will either make you or break you. Right now I'm leaning towards break. I would kill for the energy they've got," Rogers, who already had three older children from his previous marriages, told People magazine. That same year he published his children's book, Christmas in Canaan, which was later turned into a TV movie.

In 2009, he celebrated his long career with Kenny Rogers: The First 50 Years, a musical retrospective. By that point, he had recorded dozens of albums and sold more than 100 million copies worldwide.

In 2012, Rogers published the autobiography Luck or Something Like It. He received recognition for his substantial musical contributions in 2013 when he was inducted into the Country Music Hall of Fame. At the CMA Awards held that November, he also received the Willie Nelson Lifetime Achievement Award. Some of country's top performers turned out to honor Rogers, including Jennifer Nettles and Darius Rucker.

That same year Rogers released the album You Can't Make Old Friends, followed in 2015 by the holiday collection Once Again It's Christmas. Starting in December and going into 2016, the iconic singer/songwriter embarked on what he announced as his farewell tour.

In April 2018, after Rogers pulled out of a scheduled performance at Harrah’s Cherokee Casino Resort in North Carolina, the casino announced on Twitter that the singer was canceling the remaining dates of his final tour because of "a series of health challenges."

"I've thoroughly enjoyed this opportunity to say farewell to the fans over the course of the past two years on 'The Gambler's Last Deal' tour," said Rogers in a statement. "I could never properly thank them for the encouragement and support they've given me throughout my career and the happiness I've experienced as a result of that."