On a Saturday in February, nearly 100 card players arrived at a nondescript event space in Hollywood for a poker tournament with a $500 buy-in. At first glance, it looked like your run-of-the-mill upscale gambling excursion, with outfitted dealers at the dozen tables, a full bar, burgers from Trophies, and pizza from Pizzana. But anyone who’s spent time perusing galleries in Chelsea or flying to Miami for Art Basel would recognize the bulk of the players. The fact that it was going down on the Saturday of Frieze Los Angeles was no coincidence. This wasn’t the World Series of Poker but the third edition of the World Series of Art Poker, organized by the megawatt LA artist Jonas Wood. Since the game started in 2021, it’s the first and only poker tourney where artists outnumber Hold’em pros and art dealers outnumber bankers.

As the tournament barreled toward the final table, Jack Black was still in the game, and Tobey Maguire had just been eliminated, finishing 17th, and was cheering on the art dealer Jeff Poe and Christie’s senior executive Alex Marshall, who had managed to stick out the game for hours. There were established mid-career artists such as Matt Johnson, Grant Levy-Lucero, and JPW3, and, of course, Wood, who got knocked out after hours of play. Parker Ito is a fiercely competitive poker player, as is the young artist Adam Alessi, who’s been playing in games for the last three years. Among the dealers, the cofounders of tri-coastal art concern Amanita (Casa Malaparte proprietor Tommaso Rositani Suckert, former Gagosian director Jacob Hyman, and Cy Twombly grandson Caio Twombly) all stayed in the game late. But one younger dealer told me he spent his commissions made at Frieze on three buy-ins, only to lose all $1,500.

For all the star power in the building, there was only one person whose entrance made the room stop: the world-famous artist Richard Prince, who has something of a reputation as Salinger-esque upstate recluse.

"Richard rolled up and he walked around, checked it out. He told me he was coming and I was like, ‘This is incredible,’" Wood told me a few days after the tournament ended. "I was like, ‘Oh, he’s not going to play.’ And then he hung out for 15 minutes and he was like, ‘Yo, I’m going to play.’ And then he jumped in the tournament."

Prince sat down next to Avant Arte cofounder Christian Luiten, who told him reverentially that he had just made a pilgrimage to the remote Louisiana Museum of Modern Art in Denmark just to see its Prince retrospective. By the end of the game, Prince and Luiten were discussing how Prince could collaborate with Avant Arte on an edition. The rest of the room craned their necks to get a look at Prince’s card skills. Few knew that Prince had long been playing in much more hush-hush poker games organized by Wood. Before the World Series of Art Poker, the Los Angeles art world had been clandestinely coming together for a series of card games going back decades. Since the mid-aughts, Wood has been hosting gaming nights at his studio, the tequila flowing and the smell of fresh paint wafting through the room, so his artist friends and his gallerists and his friends’ gallerists could gamble while gossiping trade secrets and making backroom deals.

Then word got out, and the celebrities wanted in.

"And then Leo sees on his Instagram that we’re playing and he wants to come play with Richard Prince," Wood said.

"Leo," in this context and perhaps any outside of the High Renaissance, is Leonardo DiCaprio. Sure enough, he came through and shared a table with Prince.

"It’s kind of nutty," Wood said.

Along with DiCaprio, Black, and Maguire, Ellen DeGeneres was a regular player, Wood said, and billionaire collectors such as Peter Brant and Stavros and Theo Niarchos would get dealt in when they passed through town. Bruno Mars once dropped into a game with Wood and his wife, the artist Shio Kusaka, a serious player herself. Over the years, the art game started to mimic the art world as a whole, and went from being an insular, insiders-only bubble to one that is in frequent collaboration with the titans of other industries.

"When we started playing with some of the celebrities, it was fun because there started to be some crossover," said artist Mark Grotjahn, who has played in the game since day one. "That’s what New York had over LA: Writers and actors and fashion people and thinkers and dancers, all together. But that never really existed in the LA art world, where no one is walking. In New York, one friend meets another friend meets another friend and you’re all going back to an apartment. So with the game, we got a little bit of that here."

Perhaps we’ve collectively forgotten, but poker was really big in the late ’90s. Between the period that Matt Damon starred in Rounders in 1998 and Ocean’s Eleven in 2001, poker emerged from the dank underbelly of the casino lifestyle and entered the American home as a way to pass time in the suburbs. It also became an aspirational fantasy for aimless youngsters struggling to enter the workforce. This fantasy was embodied by a man named—and this is his real name—Chris Moneymaker. In 2003, Moneymaker, then 20-something working as an accountant near Nashville, entered an online poker tournament with $86 and emerged as the champion of the World Series of Poker, with a $2.5 million pot. Texas Hold’em tournaments were suddenly the stuff of late-night ESPN blocks and Bravo aired five seasons of Celebrity Poker Showdown shortly before going full Housewives.

"That was kind of a moment when poker really started to become popular, because people were like, ‘Oh, you can make a lot of money from not a lot,’" said aforementioned LA artist Matt Johnson, who went to high school with Wood in Boston and hired him as an assistant when Wood and Kusaka first moved to LA. "And Moneymaker was just some accountant. So Jonas [Wood] and I just sort of got into it and we were just playing on our own with pocket change just to learn how to play."

By the time the two of them got to town, a game had been going on for years led by Blum & Poe cofounder Jeff Poe, who told me he started playing poker in his early 20s while in and out of punk rock bands and working for the artist Chris Burden. By the late ’90s, Blum & Poe was going strong, and there was a game happening with fellow Santa Monica gallerists such as Robert Berman, Marc Richards, and the artist Angus Chamberlain, son of John Chamberlain. There was also a just-graduated artist new to the Blum & Poe program named Mark Grotjahn, who had paid for his BFA at UC Berkeley by playing blackjack in Reno. (He also was a successful ice cream salesman whose main conveyance was a tricycle.)

"I had my second show at Blum & Poe where I only sold one work for $3,500, and I got $1,750 for two years of work," said Grotjahn, who has since seen a painting of his sell at auction for more than $16 million. "For the next 10 months, I kind of stopped making art and I went to the Commerce Casino in East LA, the biggest card club in the country. I was playing limit, where the odds aren’t stacked against you, you just have to beat the house’s take."

He made more money doing that than selling art, and then after stopping, he went back to the private games, where he could take money off his dealers rather than the casino owners.

"I mean, at the very beginning, in the early days, it was always Grotjahn," Poe said. "He was by far the best player because he was playing a lot at the casinos and he was just…every time, he won."

In the early 2000s, Blum & Poe started showing Johnson, who got invited to the games out in Santa Monica, before the gallery moved to La Cienega in Culver City and the game moved with it. Johnson would invite his high school buddy Jonas Wood to come play, but the others had no idea Wood was an artist. One time Grotjahn and Johnson walked into Chinatown gallery Black Dragon Society, and Grotjahn realized he really liked these paintings of landscapes and interiors and sports heroes.

"I was like, ‘I really like this work,’" Grotjahn said. "Matt’s like, ‘It’s Jonas,’ and I was like, ‘Our Jonas?’"

That show sold out, and Wood reinvested all the earnings into renting a new studio on Blackwelder Street from his landlord, Ed Ruscha—a studio big enough to host his own poker games. And that’s how "the art game" was born. At first it was artists: Wood, Johnson, Grotjahn, Kusaka, along with others such as Joel Mesler, Nathan Mabry, Friedrich Kunath, Dirk Skreber, Gerard O’Brien, Raffi Kalendarian, and Rob Thom. Dealers included Poe, Black Dragon Society’s Parker Jones, Mills Morán, Frank Elbaz, Cooke Maroney, and Nino Mier.

Eventually, relative outsiders got the call-up, and that’s how the dealers ended up passing cards to Jack Black, who knew Poe and his brother, the late fashion designer Gregory Poe, through their shared involvement in the downtown music and theater world of LA in the ’80s.

"[Jeff] Poe was in a punk rock band called the Blue Daisies, and he’d show his ding-dong a lot and he was fucking crazy—the fact that he went from that to one of the most successful guys in the art world is a never-ending source of fascination for me," Black said in a phone call this week.

Black and Poe reconnected at the gallery when the actor bought a few drawings by the Japanese master Yoshitomo Nara. The gallery gave Nara his debut US show in 1995.

"I didn’t pull the trigger on the big, juicy fucking Nara painting, which is one of my great regrets in life," Black said, noting that such paintings are quite expensive these days—one sold at auction in 2019 for $25 million.

At the time, Poe also mentioned that he had a poker game with some art people, because he knew that Kyle Gass, Black’s bandmate in Tenacious D, was a poker guy. Black was all ears.

"I was like, ‘Fuck yeah, I’d love to come down and take all those artists’ money. It’ll be fun. Easy pickings,’" he said.

But the artists were good. Black said he discovered that gambling went hand in hand with making art, as both involved much calculated risk, muscular creativity, chest-beating bravura, and a teasing-out of personality. Longtime California art dealer Marc Richards cleaned out Black on the table.

"He took my money at the end. He took all of it, and as I was leaving, he said something like, ‘Come back anytime, kid.’ And it made me so mad. I definitely wanted to kill him," Black said. "And I was like, ‘Mental note: Take all his fucking money next time. That’ll be my mission.’"

Black later realized that the "come back anytime, kid" wasn’t a threat, but a genuine gesture. They liked playing with him, and he came to feel included and started coming back as one of the few people outside the art world. The collector and dealer Tico Mugrabi played. The art collector and furniture dealer Patrick Seguin got involved, and eventually brought along one of his Prouvé-loving clients: Ellen DeGeneres.

"She’s pretty rad. I don’t know if you’ve ever met her in person, but it’s different from seeing her on TV," Black said. "She’s got piercing blue eyes, and she’s a real good poker player. She’s one of those that’s got the gift. She can see if you’re full of shit or not."

Tobey Maguire was already known as a wickedly good player, having organized a celeb-heavy game that eventually was, at least partly, the inspiration for the movie Molly’s Game. He was also an art collector and friends with Grotjahn and Wood through buying their work. So he started playing at Wood’s studio.

And around the start of the 20-teens, the art game started to merge with a few other poker functions. Marshall was living in New York at the time, and he ran a game out of his Chelsea apartment that included a bunch of directors at Gagosian as well as Alex Pall, one half of hit-making DJ duo The Chainsmokers—at the time, Pall was the front-desk guy at the classic Manhattan contemporary gallery Metro Pictures.

As it happens, a lot can transpire in a few decades of playing poker with your art world friends. One time, a card dealer, who also happened to be a cocaine dealer, brought a pit bull to the game, and then showed everyone his gun. He was not invited back. One night Wood had to kick out a drunken Poe, who then profusely apologized and was let back in. Shelli Azoff, the art-collecting wife of music exec Irving Azoff, once rolled up in a Lamborghini stuffed with platters of food from Nate ’n Al’s and The Apple Pan, two legendary LA eateries—she and her husband now own both restaurants.

"Shelli’s a fucking character, and she is a badass," Black said, when asked of her skills on the table. "She’s no sucker."

After revealing quite a bit of information, those involved finally pleaded the fifth when it came to describing the attendees of the highest echelon who started coming to the game when Wood moved to a bigger studio off Beverly Boulevard in the mid-teens. When I asked Poe for details, he said, "It’d just be a golden shower of name-dropping."

"There’s all kinds of different folks, some people who are younger artists who are more at the beginning of their careers, and then there’s people who are worth a billion dollars," Johnson said. "So it’s really a rubbing of the elbows, so to speak."

Recent draftees to the art game include two of the young stars of the David Kordansky Gallery, Lauren Halsey and Chase Hall. Wood also shows with Kordansky, and the galley’s namesake occasionally plays. Brendan Dugan, a longtime associate who played in the New York game, has opened a branch of his gallery, Karma, in Los Angeles, ensuring his future participation in the West Coast game.

Newcomers are still vetted, Marshall said, even if the vetting reveals that these are people who could easily gamble away tens of thousands of dollars without ever thinking twice.

"It has to be somebody that we think is interesting and would add a certain measure of fun to the game," Marshall said. "The billionaires, of course, they can go play anywhere. But I think it’s like they want to spend four hours talking to artists and art dealers and hearing about what goes on behind the curtain. It’s fun for them, I guess."

The dream for Wood had always been to put together some kind of tourney, an annual treat that all of the gang could look forward to beyond their usual games.

At that point, the art game had merged with a game run by Eric Kim, the proprietor of Chinatown gallery Bel Ami. Kim came in to work on Wood’s vision, what would be the World Series of Art Poker, along with Eddie Cruz, the cofounder of the sneaker boutique Undefeated, who happened to own the gambling event service Casinola. They started kicking around ideas until deciding that they would stage the first tournament in the summer of 2021 in the ballroom of the Hollywood Roosevelt during the Felix Art Fair. It helped that Felix founder Mills Morán had played in the art game for years, as had Jason Chang, the owner of the hotel.

"I have some friends who are super-famous poker players, or I know people who know people who can get people to come," Wood said. "So the idea was ‘let’s invite a bunch of rad people from the art world who play poker and then let’s invite a couple poker superstars to come.’ So it’s almost like pros versus joes."

The professionals Phil Ivey and Tom Dwan came, but the tournament that year went to Dean Geistlinger, a nightclub promoter and semipro player. In addition to his cut of the pot he got a bracelet, just as in the real World Series of Poker, this one designed by Wood and the London-based jewelry designer Andrew Bunney. Geistlinger promptly sold it to the poker player Rick Salomon—who is, as Wood put it, "known from his high-stakes poker exploits, but mostly known from 1 Night in Paris." (Since his early-aughts infamy, Salomon has indeed become a regular World Series of Poker player.)

Last year’s tourney produced some memorable moments too, including the circumstances of Grotjahn’s exit. He went all in against emerging artist Adam Alessi, who had his first solo show with Clearing in Brussels last year. A crowd assembled around the pair, most of the onlookers assuming that Grotjahn had the win in the bag.

"He took me down, and he was just like, ‘Sorry, dude,’" Grotjahn recalled.

"No worries, let’s just see how your career goes," came Grotjahn’s deadpan reply.

Grotjahn couldn’t play in the 2023 game in late February, as he was in Aspen unveiling skis he designed for DPS, the ski company. But many of the other old heads were there. Black lasted longer than most, only to get eliminated by Jason Koon, a professional poker player who would go on to win the whole tourney. And Koon made good on a promise made early in the tournament: to donate all of his winnings to the Echo Park bookstore Stories, whose founder, Alex Maslansky, died unexpectedly in January.

"So he wins and he gives the big truck tip to all the dealers and everything," Wood said. "And then he gives all the cash—$31,000, or $29,000 after the tip—to this bookstore."

The tournament is not played for charity; it’s a real poker game where the winners keep the money they make. But the gesture to a bookstore Koon had never visited was in spirit with the game; that it was fun to play poker with artists if you’re a poker guy, and fun to play poker with poker guys if you’re an artist.

That doesn’t mean you don’t want to win, even if you’re a famous actor with a steady income of Jumanji movie millions.

"I was right on the fucking bubble. I was one player away. If I could’ve just lasted one more elimination, I would’ve made it into the money," Black said. "But it was not to be. But I got taken out by the champion, so that felt like something."