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Country Music News | Holler

Woody Harrelson Reveals What Really Happens During His Game Days With Willie Nelson

Much like fellow music icon Snoop Dogg, Willie Nelson has never been shy about his involvement in the herbal lifestyle. And if you count yourself among Willie’s close circle, chances are pretty high you’ll end up sharing a smoke with the country legend sooner or later.

Actor Woody Harrelson knows this better than most. He has famously spoken about how he once decided to quit marijuana—right up until Willie lured him back during a friendly poker night. According to Harrelson, resisting the Red Headed Stranger is nearly impossible.

During a new appearance on The Howard Stern Show, Harrelson pulled back the curtain on what really goes on during his hangouts with Willie, painting a hilarious and affectionate picture of their long-running friendship.

Harrelson joked that he considers himself “a hairless Hawaiian hippie,” prompting Stern to ask about rumors that he bought a new car specifically so he could plug in his weed vaporizer. Harrelson burst out laughing.

“That sounds like a wild story… I can’t imagine buying a car so that it will be more conducive to smoking herb,” he said. Then, with perfect comedic timing, he added, “I quit.”
Stern nearly fell out of his chair. “You quit weed?!”
Harrelson grinned. “No, I quit quitting. You gotta let me finish…”

From there, Harrelson got into the good stuff—his friendship with Willie and what their typical “game days” are like.

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“We do puff a few together, me and Willie,” he admitted, before Stern pushed further, asking if their sessions ever reach 10 joints a day.
Harrelson didn’t miss a beat. “Well, that would be a slow day there,” he joked, implying the real number is far higher.

Between passing joints, the two spend hours playing dominoes and chess.
“We play games all day long,” Harrelson said. “We gamble with each other too. He’s better at dominoes. I’m a little better at chess. So it evens out.”

The actor and the country legend have shared the stage many times, including Willie’s star-packed 90th birthday celebration, where Harrelson served as a guest presenter. Their bond—rooted in humor, games, and a shared appreciation for Mary Jane—has grown into one of the most endearing friendships in entertainment.

If anything, Harrelson’s latest interview proves this: when it comes to Willie Nelson, the music is legendary, the weed is strong, and the friendships are for life.

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