Certain adventurous comedians (and part-time gamblers) couldn’t resist. Cheryl Hines and David Cross, who were already playing (and winning) Celebrity Poker Showdown tournaments, signed up as the feuding Schwartzman siblings, Lainie and Larry. Ray Romano pre-scripted his own riffs as Hines’s fantasy-football-obsessed househusband. Chris Parnell took Penn’s character sketch of a poker genius and turned him into a nut-job hung up on Dune. As the rehabbing Lothario One Eyed Jack, Woody Harrelson not only performed but wrote a love song based on a 12-step program (vets Richard Kind, Jason Alexander, and Michael McKean, plus Penn’s pal Herzog and, yes, Gabe Kaplan, round out the cast). Penn structured the film, fleshed out the characters, and wrote many of their best lines, but on the rest, he literally rolled the dice.
“You were having these real reactions to these cards, but you had to have them as your character,” says Hines. “And it was intense because we all wanted to win so badly.” For the final round of the poker tournament, Penn couldn’t take his hands completely off the wheel, so he gave two characters more chips, hoping that one of them would win. Neither did. “This is why doing an improv movie makes you a better writer,” he says. “What ended up happening was the least story-efficient scenario that I could possibly imagine—and thus feels the most real.”
So how does Penn stack up against improv-legend Guest? McKean, who plays a Steve Wynn–ish billionaire buffoon in The Grand, says Penn is even more freewheeling. “Chris [Guest] and Eugene [Levy] are much more structured, a little more formal,” McKean explains, noting that Penn merrily made dramatic last-minute changes. “His technique is more like those old movies of Ping-Pong balls on the mousetraps: atomic energy. Zak’s crazy as a shithouse rat.”