There’s a saying in poker: If in the first twenty minutes you sit down at a table and you can’t tell who the sucker is, then it’s probably you.” Jennifer Tilly is teaching me about her preferred sport backstage at the Roundabout Theatre Company’s revival of Don’t Dress for Dinner, a sixties farce by Boeing- Boeing playwright Marc Camoletti in which Tilly plays a tarty mistress who has to pretend to be a cook when her lover’s wife unexpectedly stays home for the weekend. As I discover over the course of a wine-fueled night that stretches from the Great White Way to a high-stakes “house game” in a 36th-floor Tribeca apartment, there should be another rule: If you sit down at a poker table with Jennifer Tilly and don’t think you’re the sucker, you’re probably wrong.
As Tilly points out many times, she’s “not like those other celebrities who play poker.” She really knows the game. Her father had “a poker problem, I’ll put that in quotes,” she says; he introduced her to a poker video game, starting what would become an abiding obsession. She’s now a World Series of Poker Ladies No-Limit Hold’Em gold-bracelet winner, having defeated a field of 601 in 2005, and the sport’s 26th highest all-time female moneymaker (professional earnings: $700,000; recreational earnings: undisclosed). When the federal government shut down online poker sites on April 15, 2011 (a.k.a. Black Friday), she was playing up to fourteen hours a day at sixteen tables. “All of a sudden, I had all this time on my hands!” she says, laughing. Hence her gradual return to the world of actors and the living.
Hard as it is, Tilly had been abstaining during the grueling rehearsals for the play, in which she does much jumping over couches and slapping of cheeks. “Everyone is sleeping with everyone else. That’s the tagline: Extra-extra-extra-extra-marital affair. It’s like cotton candy. By the time you’ve gone to dinner, you’ve forgotten about it.” This is her first stint on Broadway in more than ten years. She last appeared at this very theater, in this very dressing room (which she shared with Jennifer Coolidge), and on this very stage, in “an infamous nude bathtub scene” in The Women. The room even has the same CD player she and Coolidge left there in 2002. It sits under Tilly’s “evil-eye talisman” to ward off bad energy and next to her “little stash of alcohol,” which she’s been depleting at the rate of a bottle of wine a day.
Tilly had been planning all along to head back down the poker rabbit hole as soon as rehearsals ended, which just happens to be tonight. She wrote of her poker jones in her Playbill bio: “She was nominated for an Oscar for her role in Woody Allen’s Bullets Over Broadway … But people remember her mostly as Bride of Chucky. After tonight’s performance, she’ll probably be playing poker.” Tilly grabs my ankle. “It’s all true. My fantastic career that’s spanned almost 30 years, and those are the things that define you.” Seeing her leave for the game, her British director, John Tillinger, seems perturbed. “You need to concentrate, darling,” he says. “I’m so frightened. When you do the big [bets], doesn’t it freak you out?” No, says Tilly. “I’m only freaked out when I’m losing.”
That Tilly wins more than she loses is a good thing, because losing “really disrupts your life,” she says. “You’re playing, and then you start canceling appointments. You’re like, ‘I have to get unstuck!’ ” Her worst loss occurred shortly before she started Don’t Dress. She sat down at an 8 p.m. game with a half-a-million-dollar buy-in because, she says, “there were a lot of idiots at the table. Well, one of them was me, it turned out.” She went “on tilt”—a losing streak turned total meltdown—and dug a hole so deep she feared she’d have to mortgage her house. She left at noon the next day, grateful she’d lost only the $100,000 she’d won in Vegas two weeks before.
“It’s like drugs,” she says. “You start off playing 25, 50 cents at the kitchen table, and then you play one dollar, two dollars, but you just want more and more thrills. That’s why I think it’s a great thing that I’m taking some time off and doing a play. I love theater, and I love acting. I just kind of forgot about it for, like, eight years. I was just in this crazy sort of vortex where I thought that poker was the most important thing in the world. Any time I would get a part, I would say, ‘Well, would I rather do this or would I rather be playing poker?’ And the answer was, ‘I’d rather be playing poker.’ ”
She says she’s not as much of a “degenerate” as her boyfriend, whom I meet when we reach the game. He runs over to give Tilly a big kiss. He is Phil Laak, 39, a professional poker player known as the “Unabomber” because he tends to wear a hoodie and sunglasses when he plays. (Tilly’s nickname is the “Unabombshell.”) Before I walk into the room, I naïvely think I might try playing a hand for kicks. Then I see Tilly’s buy-in: $10,000. Laak has $35,000 on the table. The rest of the players are a mix of investment-banker types and poker pros. The room often goes silent but for the methodical clinking of chips.
Tilly gets down to business right away: “Alcohol! My favorite time of the evening!” As she plays her hands, she whisper-narrates her thought process to me. Out of the gate, she wins $2,000 one hand, then loses $1,000, then loses $600. She always plays aggressively to start, she says: “If you don’t raise with bad hands and only raise with good ones, you become easy to read.” She raises and lowers her voice strategically. Loud: “I’m going to fold my fabulous pair of twos!” After betting big one time, she whispers, “This is just really stupid. This is a terrible plan. But, you know, sometimes you do stuff like that because it makes you look like a crazy loose player.” She ups the volume so everyone can hear: “Which I am. Crazy loose!”
If she’s playing poker on TV, Tilly says, “the starlet in me dies hard. I always just want to look cute, so I wear a lot of push-up bras and low-cut tops.” Tonight, she’s got on ripped Balenciaga jeans and a too-short T-shirt that keeps lifting up to reveal a sexy little gut with which she seems refreshingly comfortable. “The thing is, if people are really playing poker, they don’t care,” she says. “Nothing looks better to them than a pair of aces. They’re not looking at your pair. They’re looking at their pair.”
When we arrived at the apartment, a spread of Indian food lay ravaged on the kitchen counter, all but the vegetarian items cleaned out. “Poker is the most unhealthy lifestyle,” says Tilly. “You’re in the smoky environment in the casino, and you eat the most horrible crap. You don’t even get up to go to dinner. They bring you food in a tray, and you’re sitting at the table playing with one hand and eating with the other. God forbid you miss a hand! I think I aged ten years since I started playing poker.” Doing the play, she says she’s lost a lot of weight, between the physical stunts and walking 30 minutes a day from her Chelsea apartment to the theater and back. Plus there’s a lot of peer pressure to eat well when surrounded by actors. “When everyone sends out for a salad,” she says, “you feel pretty disgusting to be the only person eating a cheeseburger.” Yet when someone sends out for food at the game around 1 a.m., Tilly asks for a Philly cheesesteak with the works.
Tilly hadn’t been that precious about acting even before she got into poker. In 1998, when her career was going pretty well, she took on the role of Tiffany, the Bride of Chucky, which Chucky creator Don Mancini had written specifically for her because he couldn’t get Tilly’s Minnie Mouse–as–a–chronic–smoker voice out of his head. Tilly didn’t want to do the part at first. She changed her mind, she says, because she heard a friend was going for the role, and “I’m really competitive. My joke was, ‘Chucky killed my career!’ But it didn’t. Everywhere I go, people, like, want to hug me. Anytime I go to Popeyes fried chicken, they always throw in free biscuits because I’m Chucky’s bride.”
Plays and poker make a complementary lifestyle, Tilly says. She tried it out while doing Wallace Shawn’s Grasses of a Thousand Colors in London in 2009 and playing poker every night. Since her call time for Dinner isn’t until 6 p.m., she can stay up all night and sleep until two in the afternoon. Plus, all actors need to wind down after a performance, and poker isn’t a bad way to do it. Poker also makes up for there being no money in theater. “I mean, the play we’re doing now, it’s costing me more money to live here than I’m getting for doing the play,” she says. “But it’s because I want to live in Chelsea in my fabulous little flat. If I was staying in a place that they put me in, I would be making money, but it’s nothing next to … I mean, in poker you can make $10,000, $20,000 a night, sometimes $30,000. A few weeks ago, I made $100,000.”
Tilly has had a hard time balancing her people-pleasing nature as an actress and “someone who came from a dysfunctional family” with the need in poker to be ruthless. “In poker, when you’re doing well, everybody else is pissed off at you. Nobody loves you when you’re a great poker player,” she says. “Sometimes in tournaments I think, Oooh, my nickname should be the “Dream Crusher.” I’ll see the young kid who’s taking his college tuition to enter the tournament, and then I knock him out. I feel horrible. You have to get really hardhearted. Sometimes I’ll go easy on some really old guy, and then he just really sticks it to me a half-hour later. He’s really ungracious about it, and I think, Oooh, I should have never let him live. I should have snuffed him out when I had the chance.”
Tilly would love to do another play, and hopes to be considered for the role of Olive again in the upcoming musical version of Bullets Over Broadway. After all, she’s 53 and playing a model sex bomb in Don’t Dress now. “They’re always like, ‘Oooh, we think maybe Jennifer’s a little old to play that character,’ ” she says. “I’m like, ‘Eh, the stage, the audience is, like, 50 feet away.’ Julie Andrews played, what is that, Victor Victoria. That character’s in her twenties, when she was, like, 60.” (Andrews was actually 46.) Tilly looks at her cards and suddenly her concentration shifts. “I will check,” she says loudly to the table, then whispers to me, “I’m going to play a hand. Get prepared for fireworks!” She slips into her Tiffany voice: “I need more red wine. More red wine.” And then shifts a pile of chips forward. “I’m all in.”
It happens so fast that the only thing I know is that the new guy in the corner has very few chips anymore and Tilly has a ton. Awed comments circle the table. “Wow, Jennifer, you are a vicious killer,” says Laak and runs over to give her a kiss. She’s ahead $8,000 after that, and by the time I leave after 1 a.m., she still has $18,000, despite taking a big loss on the last hand I witness.
Though her producers probably won’t be happy about this, Tilly admits she’s thrilled that the play will end in time for her to go down to Las Vegas and play the main event at the World Series of Poker. “I’m like, ‘Oh, I really hope we don’t get extended.’ I know for a fact that as soon as I finish this play, I’m going to go out to Vegas and be as happy as can be.” She loves acting, but “I really would love to go down in history as a great poker player, too, and I feel that’s possible. But you have to put the time into it. I mean, poker was consuming me. That’s not necessarily a bad thing. Everybody has to have an obsession.”