Willie Nelson Talks Truth Behind Celebrity Poker Game Stories

Country music legend Willie Nelson is many things, including a great poker player. Recently, the crooner sat down with Dan Rather to share details behind his reputation as a highly successful player. “Poker is a serious game,” Nelson told Rather, likening it to business rather than just a fun activity.

Nelson’s mentality about poker has clearly worked for him over the years, as stories have emerged about him besting other celebrities in a big way. In particular, Rather asked Nelson about his victories against stars of song and screen Woody Harrelson and Toby Keith. The singer revealed the truth behind these rumored games and proved he’s a force to be reckoned with at the poker table.

Nelson Reportedly Won a Large Sum Against Harrelson

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Rather first asked Nelson about a rumored game between him and Harrelson, which resulted in the actor reportedly owing him a large sum of money. “He got in the poker game and he got $40,000 behind,” Rather said, recounting the version of the story he had heard. “And you wouldn’t let him leave the bus until he coughed up to $40,000.” Nelson didn’t offer a lot of details, but he laughed and refuted this rumor. “Well, that’s not altogether true,” he said. “It’s a good story, though.”

In a Jimmy Kimmel Live interview from 2021, Nelson shared more details about his history of playing poker with Harrelson. The singer explained that he and Harrelson have played poker together for several decades, and that part of his home is jokingly referred to as “Woody’s wing.” According to Nelson, this name originated from Harrelson’s tendency to stay the night if he is on a losing streak. “We play poker until late, you know,” Nelson said. “If he’s a hundred dollars, down he wants to spend the night so he can start over again the next day.”

The Singer May Have Also Taken Down Toby Keith at The Poker Table

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Movie stars aren’t the only ones who have unsuccessfully tried to take Nelson down at the poker table. As Rather recalled during their interview, the singer also bested fellow country star Toby Keith. “Have you ever heard Toby Keith’s record of ‘I’ll Never Smoke Weed With Willie Again?'” Nelson asked, referring to a funny song Keith co-wrote with Scott Emerick. The song doesn’t directly reference poker, but Rather noted that people have inferred that Keith losing money to Nelson in a game is part of what inspired it. “I’m not responsible,” Nelson laughed, not confirming or denying the truth behind the suppositions.

Keith isn’t the only artist who may have committed his marijuana-fueled poker experiences with Nelson to song. In 2018, singer Jack Johnson released his own light-hearted track about losing to Nelson, called “Willie Got Me Stoned.” The track details how Johnson started out doing well, but soon lost all of his money in the game. Clearly, Nelson knows exactly when to hold ’em and when to fold ’em.