What YouTube Pranksters Could Learn From ‘Windy City Heat’

windy-city-heatAre there any four words that cause cringe in 2018 like “It’s a prank, bro”? Hordes of well-scrubbed YouTube boys have built careers around hollering that disclaimer after performing ridiculous acts in front of unsuspecting victims. Their videos are unanimously pretty dull, capable of eliciting shocked yawps at best before being forgotten by all but the most devoted tween fans.

But when done right, pranks can be powerful stuff, and one of the greatest pranks ever pulled is 15 years old this year: Comedy Central’s 2003 documentary Windy City Heat. If you haven’t seen it (and few have, as it was buried by the network after its first airing), it chronicles the filming of a movie called Windy City Heat, the story of “sports detective” Stone Fury investigating the theft of worthless sports memorabilia like Ernie Banks’s pants.

The entire production, though, is a put-on for one man: “Scary” Perry Caravello, a print shop worker with big Hollywood dreams. Discovered at an open mic by comedian Don Barris, Perry is a wildly delusional Sam Kinison doppelganger prone to outbursts of chaotic rage. For years, Barris and collaborator Tony Barbieri (always in character as Walter “Mole” Molinski) have orchestrated outlandish situations for Perry to react to, and in 2002 they pulled their biggest prank yet with the help of producer Jimmy Kimmel.

Barris had been Kimmel’s warm-up man for years, along with hosting his own night at The Comedy Store in Los Angeles. Unlike traditional sets, Barris’s The Ding Dong Show traded in bizarre personalities and unpredictability. Perry Caravello showed up at the club in 1992, bombed spectacularly, and was immediately adopted by Barris and Barbieri, who dubbed their group “The Big Three.”

Bobcat Goldthwait plays the on-screen director of Windy City Heat while also directing the documentary. Against all odds, Caravello beats out Carson Daly (on camera) and Robert De Niro (not pictured) for the role of Stone Fury. Hidden cameras follow Perry throughout the production, capturing both his attempts to act as well as the myriad humiliations he suffers. In an interview with Grantland, Barris described the project as “…the opposite of Andy Kaufman. He tried to pull a joke on the whole world, and this is the whole world pulling a joke on one person.”

One of the first scenes they shoot for the “film” sees Perry repeatedly thrown into a dumpster by Don and Mole (who play Windy City Heat’s antagonists). The director doesn’t think it looks realistic enough, so he orders loads of runny feces be added to the dumpster, and Perry is flung into the mess over and over again. Naturally, he’s incensed and, because he’s now a “big star,” he requests a body double for any future stunts. The next day’s shooting schedule contains a sex scene with MADtv actress Lisa Arch, playing chewing gum heiress “Jiggly Wrigley.” Perry is elated, only to be informed that his double will be lensing the scene because “sex is a stunt.” Perry is ushered to his trailer, where he fumes at the injustice. When the double (who is even more slovenly than Perry) comes out of the studio claiming that he had full-on penetrative intercourse with Arch in front of the camera, it drives Perry apoplectic and he demands the double be fired. The reason this bit works is because Perry himself is the fulcrum for his own humiliation. Don and Mole just set the stage for it to happen, reacting to him perfectly and building consequences for his actions. Context makes comedy, and without a victim as compelling as Perry the whole thing would fall apart.

One of the most astounding things about the prank portrayed in Windy City Heat is how it’s still going a decade and a half later. In 2017, Barris faked his own death. A memorial service was held at The Comedy Store, hosted by Jimmy Kimmel with Perry as a featured guest. Of course, it degenerated into a series of japes at Perry’s expense until Don came out at the end alive and well. A prank of this caliber is incredibly difficult to pull off, requiring the pranksters to constantly think on their feet and adapt to the victim’s responses. Like good improv, it uses the principle of “yes, and…” as a humor-building tool.

Recently, the world of Windy City Heat reached a new audience, as conservative media personalities enraged at Jimmy Kimmel for his gun control stance dug up a clip of Perry recounting one of his lowest moments as an actor — when he gave another actor a handjob in exchange for three SAG vouchers — to the talk show host. Whether this happened or not is in dispute – it’s just one of the many bits that Barris and Barbieri regularly torment Perry with. That didn’t stop right-wing pundits from reframing the audio as proof that Kimmel was just another #MeToo sex pest who should be censured for not respecting Perry’s victimhood.

Here we saw the prank take on a life of its own, as outside context turned Perry’s confession into something totally new. It deepened his character and was especially funny to people who were aware of Windy City Heat. I’m sure Kimmel and Barris never thought that would be a result of their weird little movie, but it’s in the unexpected that a prank truly flowers.

That’s where most modern pranking falls flat: the victim is essentially unimportant, robbed of context or agency. They’re transformed from an unwilling participant to simply an unwilling audience member, and we all know how much unwilling audience members appreciate comedy. Their agency is what makes the shock of the prank potent. Without a great victim, a prank has no real power.

A great example of modern pranksters who understand this is the quartet behind truTV’s Impractical Jokers. Yes, they spend a good amount of time pulling the wool over the eyes of everyday folks, but their biggest and best are saved for each other. The hook of the show is that Joe, Murr, Q, and Sal don’t know the details of their prank until they have to perpetrate it. That opens the door to vulnerability. By becoming the victim as well as the prankster, they give their jokes depth and meaning. Logan Paul and his ilk aren’t capable of doing that, and it’s dragging the good name of pranksterism into the clickbait gutter.


K. Thor Jensen is a writer and cartoonist who lives on a small island in the Pacific Northwest. Follow him on Twitter @kthorjensen.

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