Willie Nelson has won many poker games against celebrities

Willie Nelson is known for making great country music with his friends, but the country legend has a lot more tricks up his sleeve: Did you know he’s a shark at the card table, for example?

It’s true: Nelson loves to play poker, and he’s pretty darn good at it. The singer has won high-stakes games against a range of celebrities valued at thousands and thousands of dollars. Among those who fell victim to Nelson’s poker game are Owen Wilson, Jamey Johnson and Jack Johnson – the latter even wrote a song about his experience called “Willie Got Me Stoned and Took All My Money.”

Nelson can also multitask during his legendary poker games. According to American songwriter, Waylon Jennings first played “Good Hearted Woman” for his outlaw legend during a card game, and Nelson added the line “Through Teardrops and Lachen / We’ll walk through this world hand in hand”. It became the title track of a Jennings album in 1972, and Nelson added vocals to another version in 1975. Both versions were the No. 1 country hits.

Actor Woody Harrelson is another star whose wallet Nelson eased in a poker game. During an appearance in 2018 on Jimmy Kimmel Live! recounted his experience, Harrelson said former professional basketball player Don Nelson is another household name who crossed Nelson at the card table. While refusing to say exactly how much he had lost to the country legend, Harrelson admitted that “I built a grand piano on Willie’s house”.

Fans of Nelson’s storied career know that his high-stakes poker antics are just the beginning, and he will tell more of his life story in an upcoming new documentary, announced in 2021. There were also plenty of live music outings for Nelson and his musical friends late last year: his annual Farm Aid returned to a personal format in September and his traveling Outlaw Music Festival toured again.

See images of Willie Nelson over the years: