Willie Nelson’s Wild Card: Country Legend Reveals Drug‑Fueled, High‑Stakes Poker Sessions

Willie Nelson has never been shy about his vices or his passions. The 82‑year‑old country icon has built a career on tales of outlaws, heartbreak and hazy nights on the road, all while championing causes from farm workers’ rights to cannabis legalization. Yet even longtime fans were surprised when he admitted in a recent profile that some of his favorite high‑stakes memories happened around a poker table – and that the “high” wasn’t just about the stakes.

In a candid conversation with New York Magazine’s Wil S. Hylton, Nelson conceded that he enjoys playing in high‑stakes poker games while under the influence. “Nelson is famous for smoking new friends to oblivion and then challenging them to a few hands of high‑stakes poker,” Hylton wrote. Unlike many celebrity card games, Nelson’s affairs are strictly cash‑only: debts are settled at the table, and there are no IOUs. “This has led to stories among his intimates of the time he refused to let Woody Harrelson leave the room until he could deliver $40,000 in cash”.

The poker talk wasn’t idle bravado. Nelson’s smoking habit is legendary. Hylton notes that the singer can polish off “two dozen joints” before taking the stage, and he reportedly enjoys taking pots – and pot – with equal enthusiasm. That tolerance extends to his poker pals. Singer‑songwriter Jack Johnson once immortalized the experience in song, crooning, “Willie got me stoned and took all my money”. Such stories have been part of Nelson’s lore for decades.

Nelson’s table isn’t just for musicians. Over the years, a rotating cast of celebrities has pulled up a chair. According to Hylton’s report, Woody Harrelson has been on the losing end often enough to joke that his debt could have built a “Woody Wing” at Nelson’s Maui retreat. Actors Luke and Owen Wilson are also rumored to have anteed up. Nelson first bonded with fellow outlaw country legend Merle Haggard over a poker game at his Nashville home more than 50 years ago, and the friendship flourished both at the felt and in the studio.

The all‑cash rule might seem quaint in an era of digital payments, but it reflects Nelson’s old‑school ethos. Cash eliminates disputes and reinforces personal responsibility – and it means there’s nowhere to hide when the pot gets serious. It also underscores the risks: losing $40,000 in a single session is enough to make even Hollywood A‑listers sweat.

Nelson’s appetite for poker parallels his advocacy for cannabis. Worth an estimated $25 million, he has parlayed his fame into a burgeoning cannabis empire. In 2015 he announced plans for Willie’s Reserve, a line of premium marijuana products, and has since campaigned for legalization across the United States. His duet with Merle Haggard, “It’s All Going to Pot,” released on April 20, became an anthem for the movement.

The singer’s celebrity poker nights serve as more than entertainment; they’re part of a wider network of advocacy and entrepreneurship. By normalizing cannabis use among high‑profile entertainers and professionals, Nelson aims to destigmatize the plant. His investments in cannabis ventures mirror those of contemporaries like Snoop Dogg, who backs a California start‑up focused on rapid marijuana delivery.

For all his exploits, Nelson remains a towering figure in American music. His career spans six decades, and he continues to tour, record and collaborate. The image of him sitting at a kitchen table in Maui, a joint in one hand and a stack of chips in the other, only adds to his mythos. It also underscores a truth about poker: at its heart, the game is about people – their quirks, stories and willingness to take a risk.

Nelson’s stories remind us that high‑stakes poker isn’t reserved for the casinos of Las Vegas or the televised stages of the World Series of Poker. Sometimes the most memorable pots are won (and lost) far from the spotlight, in smoke‑filled rooms where friendships are tested and legends are born. And if you happen to walk away a little lighter in the wallet, at least you’ll have a story to tell – and maybe a song to sing.