To truly tell the tale of Windy City Heat we must start in a Motel 6 somewhere in America... That's when I first saw this legendary film. It must've been 2003 or 2004. My life, irrevocably changed. Seriously. The movie is and was totally original. Like nothing before or since.
Windy City Heat was a made for TV reality film produced by Comedy Central. It first aired in October 2003. After that it went missing. I paid like $50 for a burned DVD copy of it on eBay a few years ago. Since then as more and more people spun the tale of Windy City Heat, a cult interest grew and Comedy Central released a DVD in September of 2006.
The movie is basically a 2-hour practical joke being played on a man named Perry Caravello, allegedly a gullible friend of Jimmy Kimmel and Adam Carolla. But unlike typical prank shows, it is not revealed to Caravello at the end of the film that the entire thing was a prank.
Perry believes he has been given a chance to make a movie called Windy City Heat, a crime drama about a "sports private eye" named "Stone Fury". However, there is no such film; it is all an elaborate prank played on him by Kimmel and Carolla.
Every actor, extra, or any other person who appears in the movie was paid for by Jimmy Kimmel to add to the joke.
The actual context of Windy City Heat is a behind-the-scenes docu-look at the film making process, which is really nothing more than a series of situations set up as pranks on Perry, playing on his gullibility and naïveté of the film industry.
Apparently, the joke on Perry was eleven years in the meticulous making.
Caravello was a struggling comedian and actor who was "discovered" in 1992 by Don Barris, the warm up comic for Kimmel's old show The Man Show. I actually saw a young Barris, back when he worked with MTV, hanging with Andrew Dice Clay on an old Howard Stern TV episode recently and that's what made me think of Windy City Heat again.
Perry doing his Robert DeNiro
Barris allegedly promised Caravello a chance at stardom and, along with Tony Barbieri playing the part of the perpetually stoned "Walter 'Mole' Molinski", he befriended Caravello and led him along for over eleven years.
Together, Caravello, Barris, and Mole are known as "The Big Three", which Perry excitedly describes as "the Three Stooges of the new millennium"
The film begins with the audition process, in which Perry is introduced to Carson Daly, who is also up for the role of the main character "Stone Fury" and is dressed exactly like Perry.
After a botched audition, interrupted numerous times by Barris and Mole, Perry eventually wins the role over Carson Daly.
Later in the movie, Perry is shown a wall of stars that have also been considered but crossed off the list, including Harrison Ford, Brad Pitt, and Robert DeNiro. Perry believes he has beaten out these actors for the role.
The plot of the movie he is supposed to be in is a ludicrous story involving "sports private eye" Stone Fury trying to track down the actual refrigerator of William "Refrigerator" Perry and the pants of Ernie Banks - both of whom actually appear in the movie.
The movie is directed by Bobcat Goldthwait, who is the actual director, in addition to playing the director of the fake film-within-the-film, and only speaks to Perry through a bullhorn.
Perry is followed around by at least fifteen cameras (some of which are hidden) during the filming process.
Perry is told from the getgo that he is being recorded and interviewed for the film's DVD extras. Some of the pranks include repeatedly dumping Perry into a dumpster filled with horse manure; making him drink a milkshake made of coffee, Chinese food, raw egg, pizza, and beer, giving him a case of severe diarrhea; and bringing in a stunt double to film Perry's sex scene with his leading lady.
Along the way, Barris and Mole continue to egg Perry on—performing a balancing act of pushing his buttons and stroking his ego—only causing more problems on the set, increasingly infuriating Perry and frequently leading him to scream in a high-pitched shriek. Barris regularly tells Perry to "unleash the Fury".
Throughout the filmmaking process, Perry is introduced to several individuals, purported to be real people, whose names are identical to historical and cinematic figures. Such individuals include the producer of the movie, "John Quincy Adams", casting director "Roman Polanski" (who refuses to shake Caravello's hand, played by Dane Cook), studio receptionist and soon to be co-star, "Susan B. Anthony" (Lisa Kushell), Japanese "money man" "Hiroshima Nagasaki" (who backs out of financing the production when a table of American junk food is knocked over), limo driver "Travis Bickle" (Dave Sheridan), set designer "Ansel Adams" (Toby Huss), and stagehands "Sacco and Vanzetti".
Perry never questions these coincidences, though he does express doubts as to the identity of a man purporting to be Charlton Heston, who refused to leave Perry's assigned trailer. To placate him, Perry suavely offered the old man a cameo in the film, which he enthusiastically accepts with humorous results.
The film culminates in an intentionally hindered race to the fake film's "one time only screening" during which Perry is delayed by a number of setbacks, until finally making it in time to see a select few scenes of the film. The film itself (what is actually shown of it) features laughably unrealistic special effects, lines of dialogue ripped from Casablanca and Gone with the Wind, and even a dinosaur (at the insistence of the film's financier). Following the screening, Perry is met with a round of applause from the audience, and is presented with a trophy from the "President of Show Business".
A running gag in the movie is that whenever Caravello's name appears in print (on his trailer door, and on the marquee at the film's premiere), it is misspelled. When the DVD of the film was released in 2006, the cover is listed as starring "Perry Karavello"
Just buy it or put it at the top of your Netflix queue. Take my word for it, it's fucking hysterical. And I don't do movie reviews.