Here are some of the box quotes from the cover of the DVD edition of Windy City Heat: “I’ve watched it over and over again,” rapper Eminem is purported to have said; “it gets funnier every time.” Actor Johnny Knoxville reports that “Windy City Heat is the funniest movie I have seen in many, many years.” And a reviewer from Vice Magazine notes that Windy City Heat is “quite simply the greatest movie of all time.” Perhaps it’s all a bit hyperbolic—that last quote in particular—but the basic sentiment behind these statements isn’t too far from the truth. Windy City Heat, a reality comedy (or mockumentary depending on one’s interpretation) produced by Jimmy Kimmel and Adam Carolla and released by Comedy Central, is, by almost any metric, an astonishing work. If it is authentic, then it is uncanny and unbelievable and, in many ways, utterly disconcerting. If it is completely fabricated, then it is a work of art. Either way, it’s something special—even if we’re not quite sure what’s going on.
The film claims to be an elaborate prank played on a wannabe actor named Perry Caravello. Caravello has been told that he is starring as the lead in a film called ‘Windy City Heat’ about a middle-aged private detective called Stone Fury who’s called out of retirement for one last job tracking down some kind of prized fortune. (We’re not quite sure what that fortune is—the details of the fake film aren’t actually important, and we don’t see much of the final product. Stone Fury seems to be searching for something related to the Wrigley chewing gum family fortune, but William “The Refrigerator” Perry’s fridge has also gone missing, so Fury might be on the hunt for that as well. It’s all unclear.) In actual fact, everything is fake. All the people involved are comedians or are, in one way or another, related to Kimmel and Carolla’s comedy troupe. Here is the film’s first four minutes, which essentially sets everything up.
Caravello’s two sidekicks, Don Barris and Tony Barbieri (who Caravello knows only as ‘Mole’), are in on the joke, and everybody else that is ‘starring’ in the film or is otherwise related to the project (Caravello’s personal assistant, for instance) are also stringing Caravello along. The ‘director’ of the film, Bobcat Goldthwait, puts Caravello in ridiculous situations that no real actor would be subjected to. One ‘scene’ requires Stone Fury to be thrown in a dumpster, so Goldthwait orders the dumpster to be filled with manure to make it look more realistic.
In this clip, Caravello is told to stand guard over a table prepared for the film’s Japanese financier, Hiroshima Nagasaki. ‘Mole’ appropriately injects himself into the mix, and Don later intervenes to break the two up. We see here how ridiculous the whole production is—Barbieri, playing the role of Mole, is blatantly wearing a wig and fake eyebrows, and does his best to deliberately ruin the presentation; moreover, the money man’s name is absurd, as is the idea that somebody would cancel an entire production over an upturned table.
How could anyone buy into this idiocy? Kimmel and his cohorts could not have made the whole thing look phonier if they’d tried. And yet, by all accounts, and from all the evidence presented in the film, Caravello buys into it wholesale. He really does seem to believe it all, and in his commentary for the film, he admits that some parts of the thing appear to be part of an elaborate hoax—but only some parts of it. And that’s only part of the problem here. Anybody with a modicum of common sense would, when presented with Windy City Heat, call the whole thing fake, including the premise that Caravello believes it. It’s simply not possible that anybody could be so dense as to not realize what’s going on. One explanation we might lean back on is that Caravello has some undiagnosed mental illness that somehow prevents him from understanding the gravity of the situation around him, though I doubt that even Kimmel and Carolla, notorious pranksters from their The Man Show days, would go so far so to pull a fast one on a person with some type of neural malady.
Those close to Caravello claim that he’s simply gullible, perhaps more so than any other man currently alive. Though they should obviously be taken with a grain of salt, some of the user reviews on the Amazon listing for the DVD reflect this; one individual claiming to be a friend of Caravello’s says he’s just easy to fool, and another says that he called Caravello, offering him an open mic gig at a fake nightclub to which Caravello enthusiastically agreed. And, appearing on Jimmy Kimmel Live! some eight years after this whole affair, Caravello looks easier to dupe than ever.
The dedication and time and effort exerted in making this prank come alive must be unparalleled. Windy City Heat is very much The Truman Show realized, albeit on a small scale. Here, Kimmel has constructed a false world filled with wardrobe personnel, personal assistants, secretaries, teamsters, film crew, actors, producers, sets, props, and all the myriad other minutiae that go into producing a film. It’s all incredibly real, and if they had played it straight, I’m not sure any of us would have escaped Caravello’s situation without thinking we had really starred in a film. Caravello was, after all, actually in a movie: those scenes were actually filmed, and there actually was a script, and there was actually some final product that looked like a feature. It’s just that it was all for naught, and all designed as a maniacally complex hoax on a friend. Kimmel is not beyond such grand jokes. He famously duped his comedy partner Adam Carolla into believing Natalie Maines from the Dixie Chicks was in love with him, in a prank that Maines herself was not even aware of. Looking back on it, Carolla has said he can’t believe he fell for it, but humans are notoriously good at the art of self-deceit—though few of us are quite as capable as Perry Caravello. Kimmel seems to have a bizarre, mystical power over people; something that makes them buy into whatever he’s selling.
In spite of that, I can’t help shake the feeling—perhaps, if we are being honest, the desire—that Windy City Heat is actually a mockumentary, and rather than the joke being on Caravello, it’s actually on us. There’s no evidence for this hypothesis; I can only argue from my own incredulity and say that the whole production appears too good to be true. Caravello has to be in on it. He can’t not be. If it is all a meta-level farce, and if Caravello is only pretending to be the goat, then this is one of the finest productions ever set to film—just as good as Woody Allen’s Zelig, and coming in range of (and perhaps even surpassing) This Is Spinal Tap. But if it’s legitimate, and if Caravello was really fooled, then Windy City Heat is an amazing document: a transparent look at the art of the hoax. The best type of deception may be to make everything as bizarre as possible. The crazier things get, the more people seem to believe—Ashton Kutcher’s Punk’d is evidence of this—and Windy City Heat is the crazy prank to end all crazy pranks.