In the Aughts during the resurgence of poker, celebrities playing the game became fashionable. Especially on television, some shows were specifically created for celebrities to play the game for charity (anyone remember Celebrity Poker Showdown?). When it comes to these celebrities, would you believe that country music legend Willie Nelson has built a reputation as a card sharp? If you ask some other celebrities, Nelson has been able to lighten the wallets of some of them and for considerable amounts of money.

A Song Was Written About Nelson’s Poker Prowess

According to an article from Carena Liptak of TasteOfCountry.com, Nelson is known in the music and entertainment industry just as much for his poker prowess as for his songwriting abilities. Liptak points out that Nelson was not above mixing his two pleasures – music and poker, in this case – even to the point of demoing songs for other artists. Liptak states it was during a poker game that Nelson played the song “Good Hearted Woman” for fellow country superstar Waylon Jennings, who would take Nelson’s song and make a massive hit out of it.

There are several other tales of Nelson earning some money on the felt. Nelson has played against actor Owen Wilson and fellow musicians Jamey Johnson and Jack Johnson, with Jack writing about Nelson’s poker exploits in a song called “Willie Got Me Stoned and Took All My Money.” Another person who admitted to losing copious amounts of money to the “Red Headed Stranger” is actor Woody Harrelson, who admitted that he “built a wing on Willie’s house” with money that Harrelson has lost to the country superstar.

Plenty of History of Celebrity Interaction with Poker

Poker is America’s National Pastime (yes, they stole it from baseball!), so it is not strange that celebrities like to step to the baize for a card game. At the World Series of Poker, Welcome Back, Kotter star Gabe Kaplan more than held his own against some of the greatest players in the world back in the 1970s. Kojak star Telly Savalas was also a part of these games.

When the movie Rounders was in pre-production, stars Matt Damon and Edward Norton lurked and watched the action before stepping into the 1998 WSOP Championship Event – Damon was knocked out by a legend of the poker world, Doyle Brunson. Norton went out when his full house was beaten by four of a kind.

For many fans of poker, however, Celebrity Poker Showdown was the first exposure to celebrities playing the game. Notable actors such as Ben Affleck, Don Cheadle (who would go on to play in the NBC National Heads-Up Poker Championship), Allison Janney, Hank Azaria, the late Carrie Fisher, Paul Rudd, Wanda Sykes took part in the tournaments between 2003-2006. Champions of the series included comedian Nicole Sullivan, actor Maura Tierney, Late Night host Seth Meyers, actor Mekhi Phifer and comedian Brad Garrett, among others.

Is there a chance that Nelson might make his poker debut somewhere outside a cash game, perhaps a tournament in one of the casinos in Las Vegas? It would be highly unlikely as, with Nelson being 88 years old, stamina for long run tournament poker is probably out of the question. Still, it is cool to know that, among his other talents, Nelson also enjoys a game of cards.

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