No One Will Ever Top Woody Harrelson And Sean Penn’s Escalating Prank War

Woody Harrelson is hosting Saturday Night Live this weekend, which is as good a time as any to revisit one of my very favorite stories about Harrelson, who has so many to choose from. I love a good prank, and Harrelson and Sean Penn are apparently like the Winston (New Girl) of pranks: They take them to ridiculous extremes.

Their prank war started on the set of The Thin Red Line, the 1998 Terrence Malick film that featured both Harrelson and Penn. It began innocently enough. At one point, Harrelson lined Penn’s helmet with pre-chewed bubblegum. Another time, Harrelson threw a live snake into Penn’s trailer.

That’s pretty good, but it’s nothing compared to what followed.

To get Harrelson back, Penn passed around 2,500 flyers for a “Woody Harrelson Day” event, and called the local radio station in the Australian city they were filming in to get them to announce that Harrelson would be spending the day in the park signing autographs for $10 a pop. According to some reports, Harrelson never showed up for the event, although according to co-star Nick Nolte, Harrelson did arrive, but signed autographs for free.

Then it gets really interesting, because to get Penn back for this, Harrelson enrolled Nolte for help. Harrelson also hired two real cops. Then, in the middle of the night, Nolte called Penn saying he’s been in an accident, and that he needs Penn to come to the police station and vouch for him. Penn rushed over.

Here’s the crux of the prank, in which a hostage situation was basically staged and someone held a gun to Penn’s head, from a 2010 interview with Nolte over at the AV Club:

So [Sean Penn] came and knocked, and I was at the picnic table. The cop went down the hallway and he brought him in. Now, the cops are getting nervous once they had to start to act. The whole feeling became like it was a police station. He sat Sean down and he started very fast explaining what the situation was and it’s, “No problem, you need me to vouch?” He looked away once and Sean whispered to me, “Were you drunk?” And I said, “No. I hadn’t been drinking.” And the other guy got up and they went down the hall to take a pee. It wasn’t anything that drew attention. But as we were sitting there, all of a sudden we hear this boom! Bang! Crash! Bang! And this cop with us took off and went down the hallway. And then it was even worse: bang! Crash! Boom! And Sean said, “What the f*ck’s going on?” I said, “Don’t know. I don’t know.”

Then Sean got up and he started to head right toward it. And I said to myself, “If there’s a gun, it’s gotta happen now.” And just as he got to that door, sure enough, “Boom! Boom! Boom!” Three shots. He came hauling ass back into that room, went to the back door, tried to get out. It was locked. He went to the side windows. They were locked. In come the cops, and they hit the floor.

I started to crack up, so I went up in the corner, hiding in the corner, and Sean was on the floor. And in comes this guy going, “I’m going to get the f*ck out of here, you motherf**ker! I’m gonna kill somebody! I’m gettin’ outta here! Sean, you’re gonna drive me out of here.” And Sean very gingerly got up and says, “No reason to shoot. I’m trying to go wherever you want to go. Don’t shoot anybody.” And the cop sitting on the floor said, “The keys are on the desk.” Sean got the keys, he went to the door and unlocked it and opened it, and there was Woody with his flash camera.

Boom! Roasted.

Harrelson started shouting, “I am king! I am king!” to celebrate the prank war victory. Later that night, Nolte got blitzed with the cops and Penn confessed, “You know, if I had been in L.A., I would have had my gun, and somebody would have been killed.”

Because the best pranks always involve the threat of death.

But the prank war wasn’t quite over yet, because Penn had to get Harrelson back. From Mike Medavoy’s book, You’re Only as Good as the Next One, via IMDB:

After driving 40 miles into the rustic outback of Australia, where their movie was being filmed, Penn pretended to get stuck and Harrelson got out to push. Medavoy says, “Sean slammed it into four-wheel drive and literally left Woody in the dust, stranded, in the middle of the night, with no food, no water and no way home except on foot. Woody was eventually picked up by an extra on his way to work.”

And that’s how you win a prank war, folks. You leave your buddy out in the middle of nowhere and drive away, leaving him with no food or water and no way home.

Sources: The AV Club, Scribol, and New York Daily News via People Magazine