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How Woody Harrelson Gambled Away His Fortune

Dennis Farina, Woody Harrelson, and Woody Harrelson’s sideburns star in The Grand, screening during the Tribeca Film Festival.Photo: Courtesy of Tribeca Film Festival

On Saturday, the Tribeca Film Festival will announce the winner of its audience award, and we’re hoping honors will go to The Grand, Zak Penn’s hilarious poker-tournament mockumentary in which Cheryl Hines, David Cross, Richard Kind, and others play real games in real time, and in character. The film’s splashy premiere took place a week ago at the Borough of Manhattan Community College, with an after-party at Lotus, where celebrants drank liberally and played poker on all three floors. Somehow, New York had three reporters there: Jada Yuan, Bennett Marcus, and Jocelyn Guest. They spoke to the cast.


Cool eye patch. But I thought Woody Harrelson was the one who wore one in the movie?
I’m actually wearing this for medical reasons. I got a scratch on my cornea when I was younger and every once in a while it flares up. I wish I had a funny story to tell.

D’ohh! Uh, so did your gambling skills improve over the course of this movie?
It was probably status quo. I actually played a lot in regular tournaments when I wasn’t shooting, and I won $1,800 once. I came in third once and got $600, and there were a couple of times I got shut down. But I got to the final table every time.

Not bad. Which actor sucked the most at poker?
Woody. No, I take that back. Chris Parnell was the worst. He was really stressed out, mostly because he doesn’t know how to play poker.

Any advice for amateur poker players?
Yeah, try to learn as little as you can. Don’t learn from your mistakes. Then get in touch with me and we’ll play one weekend.


How are you at poker in real life?
Pretty good, but in the movie, I played very poorly, because I was playing a character. When I’m in a gambling town, I come into a casino and I’m not gregarious. I’m there to play.

Got any gambling horror stories?
I do. My children have gone hungry for about three days.

How did this compare to other improv movies you’ve done?
Well, I was in For Your Consideration, and Christopher Guest is much more detailed. Zak is more fly by the seat of your pants. My knees were a little weak. I did not know what would happen next. You know that tingling in your thighs you get when you’re scared? I had that.

Who was the worst poker player on set?
Dennis Farina. He was tired of filming. He wanted to go out and meet friends, so he played the wrong hand, just to get out.


We heard you threw the final poker match in the movie so you could leave the set.
[Laughs] Who told you that?

Richard Kind.
[Laughs harder] No comment.

What did you learn about poker while making this movie?
Professional poker players have the same focus and determination that athletes have. If you’re playing poker for a living, you’ve got to have concentration, and that’s a matter of training. And you have to concentrate on not the cards you’re playing but the cards other people are playing. If you do that, you’ll come out ahead.


Ever lost big?
Oh, I have a lot of losing stories. [Laughing.] When I went to do Rush Hour 2 in Vegas, I set aside, like, you know, $10,000 or $20,000 for the three months I was going to be in Vegas. And I think I got up to about $200,000 with the $20,000 I started with. And by the time I left Vegas, I had $20 in my pocket. So that’s a lesson for all of the people that think they’re going to leave Vegas with money. It’s not going to happen.


Ever lose your last dollar gambling?
Oh, yeah. Oooooh, yeah. All too many times. One time I went to Las Vegas with my brother, just to check it out; we were just passing through, heading toward the Midwest. So we stopped at one of the hotels — I forget, Caesar’s Palace or something — and we go in and start gambling. I lose everything I have, and it’s, like, really early in the morning, and for some reason I can’t get any more money. I couldn’t even pay the valet guy. I literally had to beg someone — this is many years ago — but, uh, I had to beg money to pay the valet, to get the car.

How do you know when to stop?
When all the money’s gone, you know it’s time.


What’s it like playing cards on camera as opposed to just for fun?
It was terrifying, honestly, because I’m really not a poker player. It was a challenge to be in character and actually try to compete against Richard Kind, who is a serious poker player. And my character is supposed to be a poker math genius, so to sort of help sell that, you know, I needed to do well in this game. I think I did okay.

Got any tips for amateur poker players?
I’m an amateur! I’ll play Trivial Pursuit — anything except for the sports edition — Pictionary, whatever. I’m up for any board games, but I don’t really play poker. I played maybe two or three times before the movie. I don’t really like it.

We heard it stressed you out.
What stressed me out was the final game, because we were playing for real. You’re trying to act and play poker against people who really play poker while you’re improvising dialogue. It was very stressful.

Did you feel like you were going to lose?
I got horrible cards, so I played really tightly. I didn’t really enter into many hands. Zak could see all the cards while we were playing, and he said I actually played it really well, and I felt good about that.

How Woody Harrelson Gambled Away His Fortune