Poker is a popular card game that can be played casually or professionally. Even Hollywood stars aren’t immune to the allure and high-stakes excitement of a good poker round. Many Hollywood stars even get together for their own unofficial World Series of Poker (WSOP), subtly named the World Series of Art Poker, organized by LA artist Jonas Wood.
The third edition of the World Series of Art Poker, held in 2023, brought together Hollywood artists and art dealers, including superstar actors Jack Black and Tobey Maguire, as well as Leonardo DiCaprio and Ellen DeGeneres.
Poker became especially popular in the late 90s, with poker- and casino-themed films — like Matt Damon‘s Rounders in 1998 and Ocean’s Eleven in 2001 —dominating the box office at the time. As such, it’s no surprise that Hollywood stars were quick to jump in on the trend — and even excel at them. In this article, we’ll be looking at four Hollywood A-listers who go all-in with playing poker.
Tobey Maguire
Perhaps best known for his role as Peter Parker and Spider-Man in Sam Raimi’s Spidey trilogy, Tobey Maguire is also especially good friends with fellow A-lister Leonardo DiCaprio, another poker enthusiast. In a previous post, we highlighted fellow Spider-Man Andrew Garfield‘s praise for the actor and his wish to return to the superhero role alongside co-stars Maguire and latest Spidey Tom Holland.
As early as his web-slinging days, however, Maguire has spent lots of time raking in prize winnings at poker tables. He took up tournament poker in 2004 and was tutored by poker pro Daniel Negreanu. Maguire participated in a 2020 charity match hosted by ACR Poker, which featured other celebrities and Americas Cardroom pros like Ebony Kenney, who won overall. The stay-at-home poker tournament saw Hollywood names like Ben Affleck, Matt Damon, Tom Brady, Adam Sandler, and more, with $1.2 million raised for Feeding America – the largest hunger-relief organization in the US, providing meals to over 40 million people annually.
Jennifer Tilly
Known for her distinctive speaking voice, Jennifer Tilly rose to fame when she played Tiffany Valentine in Bride of Chucky and throughout other installments of the Child’s Play film series. She was also nominated for a Best Supporting Actress Academy Award for her role in Bullets Over Broadway in 1995.
When not voicing iconic characters, Tilly is also quite the decorated poker player. In 2005, Tilly won the $1,000 Ladies’ No Limit Hold’em, bagging $158,335 and the coveted World Series of Poker bracelet. Previously married to The Simpsons creator Sam Simon, Tilly has been in a long-term relationship with professional poker player Phil Laak, regularly sharing fun photos of the couple and their activities on her Instagram profile. Like Tilly, Laak also holds a WSOP bracelet and a World Poker Tour title.
Ben Affleck & Matt Damon
Mentioned throughout this article, creative duo Ben Affleck and Matt Damon might as well be listed as one. The two best friends have worked alongside each other for decades, even bagging an Academy Award for Best Original Screenplay for their work on 1997’s Good Will Hunting. Damon, in particular, is known for his role in 1998’s Rounders — considered one of the best poker films ever. Damon has since teased that a Rounders sequel may be possible in the future, since the cast involved, including Edward Norton, are more than willing to do it.
As mentioned, the duo joined other charity tournaments in the past, including a No Limit Texas Hold’em tournament by WSOP to fund efforts to end the crisis in Africa. Damon and Affleck were also part of the star-studded hold’em tournament held for Feeding America in 2020. A year after the charity poker tournament, Ben Affleck rekindled his romance with ex-partner and fellow Hollywood household name, Jennifer Lopez, announcing their second engagement in 2022. While the pair has since separated and filed for divorce, Affleck was known for his attention to privacy throughout the public relationship.
