#49: Windy City Heat

Release Date: October 12th, 2003

Format: Streaming (YouTube)

Written by: Don Barris, Tony Barbieri, and Jimmy Kimmel

Directed by: Bobcat Goldwait

4 Stars

It was some time in 2006 that I started getting this unusual request from customers when I was working at the video store: “Do you have Windy City Heat?”

We did in fact have one copy of Windy City Heat, and it was perpetually checked out, to customers’ disappointment. But what in the hell was Windy City Heat? I had never heard of it, and from the title it sounded like some sort of B-movie or erotic thriller. I had no idea.

One day, to my surprise, a customer asked if we had it in stock, and whadya know, we did. 

It was then that I saw the DVD for the first time. I know you’re not supposed to judge a book by its cover, but Jesus Christ, the cover looks like absolute shit. It’s terrible. The center of it has a headshot of a middle-aged guy in a fedora screaming, and on each side of him are headshots of a guy in a top hat and a guy in a terrible wig. These gentlemen (Perry Caravello, Don Barris, and Mole) comprise “The Big 3,” the “Three Stooges of the new millennium.” Below the three “stars” of the movie are some of the other featured actors in Windy City Heat, luminaries such as Carson Daly, Adam Carolla, Bobcat Goldwait, Lisa Kushell, and Jimmy Kimmel. Not exactly a star ensemble. All of this DVD photoshop hackery is atop a beige background, with “Windy City Heat” in big red and black block letters across the front and a bullet that looks like it came straight out of Microsoft WordArt. 

It really is in the running for ugliest DVD cover ever. It is so atrocious that for months, despite customers fighting to rent a copy of it, I dismissed it completely. How could some straight-to-dvd Comedy Central movie starring D-list TV talent be any good? 

But as time wore on, and the requests from customers remained steady, I finally relented one night. Alright, let’s see what the hell Windy City Heat is all about.

To put it succinctly, it is the funniest movie I have ever seen. I’m not saying it’s the “best” comedy ever made, but if your criteria for a comedy movie is simply “How funny is it?” this is the pound for pound champ. I’ll put it up against Blazing Saddles or Step Brothers or Anchorman, whatever. This virtually unknown comedy will cook them all. I’m still trying to find an opportunity to see it with an audience in a theater to validate my opinion. I’m convinced it would bring the house down. 

And beyond being the funniest movie ever made, it’s innovative as well. The story involves real life Perry Caravello (all too real), an aspiring Hollywood star who has been toiling away at the margins of the industry for the past ten years as a stand up comedian and movie extra. His friend Don Barris, an actual comedian and regular at the world famous Comedy Store, has managed to snag an audition for Perry for an upcoming movie, Windy City Heat. Tagging along to the audition is their best friend Mole, a drug addict and complete lunatic (unlike Perry and Don, Mole is not a real person, but rather he is played by Tony Barbieri, a writer for Jimmy Kimmel Live!). On the way to the audition, Don informs Perry that the producers of the movie want to shoot a bunch of behind the scenes footage for the DVD, so when they get out of the car Perry will be mic’d up and there will be cameras following them inside. 

What Perry doesn’t know is that there is no movie. This is all a ruse. An elaborate hoax. For the next few weeks dozens of people will stage a fake movie production that Perry thinks is going to make him a star.

You might ask, how could this possibly work? This can’t be true. How would someone fall for this? 

The answer is that Perry Caravello is a world-class moron. A complete dope. And he’s absolutely deluded by his dream of being a Hollywood star. In his words, “I’ll do anything to be a star, anything.”

I could go on and on about all of the great bits in this movie. I’ve seen it dozens of times over the past almost twenty years. Here are a couple of my favorites:

• When they arrive at the audition, the Big 3 see Carson Daly exiting the audition room. He’s dressed exactly like Perry (cheap leather jacket, black fedora, black jeans, and a black fanny pack). Perry can barely hide his rage. Then it cuts to an interview with Perry: “When I see Carson Daly wearing the fanny pack, wearing the jacket, wearing the hat, I’m looking at…somebody that wants to be me…and I’m thinking in my head, this is somebody that needs his ass kicked, bad. Real bad.”         

• Perry has an assistant, “Burt Ward,” that Don is mercilessly cruel to throughout the filming for no apparent reason. My favorite Don line to Burt: “Burt, it would be polite if you opened the fucking door for Perry. Let’s go, let’s move it fuck face.”

• Speaking of Burt Ward, there’s a running gag throughout the movie of people being named after celebrities. Perry is too much of an idiot to think twice about how this movie production includes such people as John Quincy Adams, Roman Polanski, Susan B. Anthony, Travis Bickle, Ansel Adams, and Frances Farmer.

• Windy City Heat is sharing a studio with Schindler’s List 2. During a break in filming Perry, Don, and Mole are sitting around watching Nazi soldiers play a pickup game against Jewish concentration camp prisoners. One of my favorite Don lines: “Hey, the Jew just hacked ya!”

• As filming comes to an end, producers show the Big 3 some of their prototypes for merchandising. One of their ideas is action figures, and Perry’s action figure has an enormous pot belly and double-chin.

• And maybe the greatest scene in the movie is when one of the film’s financiers, Hiroshima Nagasaki (again, Perry is clueless), is going to visit the set and the Windy City Heat director, real life Bobcat Goldwait, has carefully laid out a table of American delicacies to welcome him. Perry is given strict instructions to guard the table with his life, because if the visit from Mr. Nagasaki doesn’t go well, the funding for the movie could be in jeopardy. Right on cue, a drug-fueled Mole enters the room. Things go about how you imagine, and it’s absolutely hilarious.

I cannot say enough about how brilliant and funny I think this movie is. Part Truman Show, part Jackass, but with an absurdist quality and layers of jokes that make it ripe for repeat viewings. It’s a shame that it didn’t get any sort of wide release, but it has become a certified cult classic.