Charlie Sheen Catches a Flying Faygo and Says “Whoop-Whoop Winning” at the Gathering of the Juggalos


Charlie Sheen
Hogrock Campground, Cave-In-Rock, Illinois
The Gathering of the Juggalos
Saturday, August 13, 2011

Better than: Two and a Half Men

It’s probably our fault. What did we, or anyone, really expect? That Charlie Sheen would come onstage to the Gathering of the Juggalos and burst into flames? That given his long-documented interest in strippers, the actor would summon the young lady who’d won the Miss Juggalette contest earlier in the day (by ejaculating on command) and invite her to become his newest goddess? Or that he’d actually walk among the Juggalos at some point and pose for photos along the infamous Drug Bridge?

All those memes in one place? The Internet might explode.

Back in the spring, the thought of Sheen showing up to the Gathering of the Juggalos seemed like the potential for chaos. Entertaining Juggalos often brings out the worst in performers, and back when this was first discussed, Sheen was still making every bad decision imaginable, very publicly. Something huge was bound to happen.

The Illinois State Police thought so. There’d been mandatory sobriety checkpoints set up early in the morning, less than a mile outside the campground gates–a totally new development this year. When asked why, one officer explained, “We figured this year with Charlie Sheen, that would bring a lot of them.” (He did not elaborate on who he specifically meant by them.)

The possibility of a debacle even excited Insane Clown Posse’s Violent J. As he told us last spring, “That’s one of those situations where I don’t know how good it would turn out or not, but I know everybody would want to see what happens.”

What happened was that in the middle of George Clinton’s amazingly life-affirming set, an enormously imposing tour bus rolled through the Juggalo crowd around 9pm, more than three hours late. And then, right before Psychopathic Records rapper Blaze Ya Dead Homie came out, the guy who once was Chris from Platoon walked out waving. He looked far better than you’d expect.

His banter was an amalgam of tiger-blood nonsense and Juggalo vocabulary, meaning that it would never make sense in any other circumstance, ever. Like this: “Time to get totally unhinged. Want to feel the burn. Are you still ‘Whoop-Whoop winning’? You ‘Whoop-Whoop Winning,’ alright? Let’s hear it for Twiztid!” Pause. “You guys are fucking asleep.”

Juggalos did, per usual, attempt to bean him with shit. Like with an airborne glowstick, which he dodged. And then with an opened Faygo can that the Eight Men Out star caught mid-air with his right hand–winning!. The red soda poured down his right arm and dripped on his blue button-down shirt.


The Juggalos seemed mostly happy that Sheen actually showed to acknowledge their existence publicly. “Juggalos–We got Charlie Sheen!” said Matt-O, a 24-year-old Ohioan who’d been waving a Charlie Sheen poster on a stick from the crowd. “That’s fucking winning, for real.”

Enjoy the rest of our Gathering of the Juggalos coverage here.

Related: Photos from the Gathering of the Juggalos 2011

Photos of Juggalette Cuties

Photos of Naked Juggalettes (NSFW)