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First things first: I’d never played poker before in my life. But when you find yourself in a Molly’s Game–esque room, you do as the Maguires do: bet big, keep a straight face, and pray for the best.
Record scratch, freeze-frame, rewind. The setting: a random weeknight at the Chateau Marmont. The occasion: the Academy Awards, sort of. In the midst of a historically chaotic Oscar season, one high-profile nominee has been riding the campaign wave with a sense of unshakeable unbotheredness so sturdy that it must be genuine. Since scoring his second Best Actor nomination for his performance as Bob Dylan in James Mangold’s A Complete Unknown, Timothée Chalamet has had an awards season marked mostly by unique red carpet fits, a successful gamble as host and musical guest on Saturday Night Live, and otherwise not sweating the outcome of the race (or at least, not appearing to).
True to form, when Cartier offered him an evening to celebrate his appointment as one of the Academy’s five picks for Best Actor of 2024, Timothée swerved on an atypical brand-ambassador dinner, opting for something much livelier, more unexpected, and gleefully random: poker night.
Cut to a posh evening in a spacious suite on the sixth floor of the famed LA hotel—three full poker tables complete with dealers, bartenders, a DJ playing everything from Sinatra to “Let the Beat Build,” and a rooftop patio that included a cigar station—filled with friends both close and equally famous, including Tobey Maguire, Kevin Hart, Rich Paul, Nathan Fielder, Theo Von, Kid Cudi, and Kylie Jenner, with me as the outlier taking it all in.
The mood never rose above chill, so much so that at first you’d be forgiven for assuming the poker of it all was just thematic window dressing. Timothée, in a full leather Chrome Hearts fit, shot the shit with Hart and Paul, as more of his guests milled around. I scanned the room for the most fascinating person on the guest list: a hard-core poker coach, who was described to me as being like “a character from The Penguin.” (Sadly, I did not make his acquaintance.)
But you don’t invite legendary card sharks like Tobey Maguire to a night like this just to stand around and sip Stellas—that’s a normal Tuesday at Delilah for him. My dog Spidey started at the rooftop bar, but you could tell those poker chips were speaking to him like the Green Goblin mask; slowly but surely he kept—inadvertently?—inching toward the tables inside before it kicked in for everyone else that, oh, yes—we were here to play cards.
If this sounds like that Ocean’s Eleven scene where WB heartthrobs woefully stumble through a poker-101 class with Coach Rusty, the A-listers here couldn’t be further from novices. If anything, I was the Topher Grace in the room. Within minutes, Kevin Hart liberated Marcus Mumford of his chips and sent him back out to the bar to think on his betting mistakes, leaving an open seat for me to pull up right next to the man of the hour, at which point I came clean about having absolutely no idea what I was doing.
I didn’t ask Big Tim how he’d curated the guest list, but assumed he had played with everyone here at some point or another. As curious as I was to watch Nathan Fielder play, I reasoned it was a good thing he was at a different table, since the guy who made The Rehearsal surely must have an impenetrable poker face, which Timothée confirmed. “He’s a beast,” he said, as if a time when Fielder cleaned him out was flashing before his eyes. Rich Paul, who also seemed like a formidable opponent, opted to just observe, but assured me he’s skilled in any arena that involves gambling.
The second surprise of the night: Tobey being among the first casualties to go all in and lose, at a table behind us. Meanwhile—while Hart continued to do damage to our table with maniacal glee, like the “we clown around here” meme come to life—I was holding steady somehow, thanks to some crucial coaching from Timothée and our dealer. Timothée and Kylie went head-to-head once, on a defeat he graciously and proudly accepted. (She was, sneakily, one of the most formidable players at the table, raising big bets with the confidence of a high roller, as a woman who’s up Bs should.) I even survived a face-off with her and a few others, accruing a nice pile.
Then Paul and Hart departed for dinner, leaving an open seat across from me, filled by none other than…Tobey Maguire. I gulped. He laughed, saying that he’d just got booted from the other table, so how scary could he really be, right? Well, to the shock of absolutely no one, after a few hands, one came down to me and Tobey. I had what, in my 60-minute crash course, appeared to be a good hand. He raised, I matched. And of course he won—he didn’t even do the ‘flip the edge of the cards up for one last peek’ bit. Clearly that loss earlier in the night was just a warm-up set. There’s no hand he hasn’t seen before; if anything, losing to the Posse Vice President would be an honorable death. But I didn’t die and get cleaned out at the very least, as we laughed about later (even I know better than to go all-in against a GOAT).
Overall it was a private but far from debaucherous night, one that our host didn’t even seem to be all that interested in centering on himself. Awards talk never came up in conversation. Behind closed doors and in familiar company, the young Chalamet is just as laid-back as his press tour suggests. We’ll see if his luck holds until Oscar night—but even if it doesn’t, it’s a safe bet he’ll be back to play another hand soon.