Playing poker, or even losing a poker match, to country music icon Willie Nelson sounds like a fever dream or an eccentric bucket list item for most of his fans.
However, for several Hollywood stars, poker nights with Willie Nelson are a timeless tradition.
Recently, the Red Headed Stranger appeared as a guest on “Jimmy Kimmel Live.” Kimmel was out and guest host country artist Maren Morris was instead around to speak with Nelson.
Maren Morris brought up the fact that Nelson is a huge fan of poker and has been hosting poker nights for years. He then confirmed that it’s been going on for about 20 to 30 years as of now.
His friends join him over at his epic house in Spicewood, Texas. Given his iconic status, Willie Nelson has some pretty legendary friends as well. He often invites over A-list celebrity guests for some good old-fashioned, money-losing fun at his place. This includes stars like Woody Harrelson and Owen Wilson.
Woody Harrelson specifically has been a staple at these poker nights for decades now.
“We play poker until late, usually, if he’s a $100 down he wants to spend the night so he can start over again the next day,” Nelson said.
Maren Morris then talked about the wing of the house they play poker in every week. Apparently, the wing is dedicated to Owen Wilson and Woody Harrelson because they’ve lost so much money to Nelson over the years that they’ve played a role in creating it.
Nelson had a sly response of, “Well, that’s a good story, let’s say it’s true.”
Willie Nelson and Woody Harrelson Friendship
Willie Nelson and “Zombieland” actor Woody Harrelson have a pretty long and epic friendship.
During an appearance on “The Ellen DeGeneres Show” in 2018, Harrelson spoke about their relationship. Specifically, he talked about how Nelson appears to be the king of peer pressure.
Harrelson shared that there was a period of time in which he had quit smoking of any kind. Each time he ran into Willie Nelson, the country artist would pretend like he forgot. After a pretty epic game of poker, that time away from smoking quickly ended.
“I was in a celebratory mood and he hands me that pin and I was just snatched and it was like ‘ah, f— it.’ I take a big draw of it and he says ‘Welcome home, son,'” Harrelson said.
Although the idea of Wilson and Harrelson funding a wing in Willie Nelson’s house is a bit outlandish, Harrelson has definitely lost a fair share of cash over the years. On a “Jimmy Kimmel Live” appearance from 2018, Harrelson wouldn’t say just how much he’s lost.
Kimmel joked, “Guys you got to go see this movie because if you don’t, Woody could potentially have his home repossessed and by Willie Nelson of all people.” At the time, he was on the show promoting his appearance in “Solo: A Star Wars Story.”