A fascinating failure. Or maybe a one-of-a-kind success – depending on your tolerance.

For a film available to stream in full on YouTube, you could do a lot worse.

To call it imperfect is generous – yet it’s still noteworthy in its uniqueness. Not exactly recommendable, but undeniably interesting. Film fans may find it worth a look for that reason alone.

The Most Expensive Prank Ever

This was a major undertaking: a fully staged feature-length prank targeting one man, Perry Caravello, who believes he’s starring in a legitimate Hollywood movie. That premise is both the film’s genius and its moral liability.

Does Perry truly believe it? That question lingers throughout. He is such a bizarre, dislikable figure – loud, crass, oblivious. The audience is asked to laugh at him, yet it’s hard not to feel some level of pity. He has almost no redeeming qualities, which complicates the comedy. His dialogue is endlessly cringeworthy. Redemption would have helped.

Still, the production is wildly ambitious.

They filmed in the rain – literally. You see the lens dripping. Actors soaked. Dialogue delivered mid-downpour. It shouldn’t work, and often doesn’t – but that’s part of the joke.

Adam Carolla appears as a gladiator and delivers one of the film’s most impressive moments: Steering Perry into absurd improvisation while the skies unload. Props to the Ace Man.

Cast Breakdown

The acting is a mixed bag. Don Barris gives the strongest performance, finding realism in even the wildest improv. His scenes – especially when berating Perry’s assistant – are darkly funny and oddly grounded.

Tony Barbieri, by contrast, is overamped. The wig distracts. He’s sweaty, hyped, a little too eager to jump in. He still serves the gag but rarely elevates it.

Bobcat Goldthwait (as the film’s director) is fantastic. He uses a megaphone in every scene – including behind-the-scenes moments – and his improv often shifts the direction of scenes in real time. His presence offers occasional meta-commentary on Hollywood absurdity.

The smaller players shine. Perry’s assistant nails every cue. The fake love interest delivers an inspired Hepburn impression – made funnier by the fact Perry doesn’t notice. (The fact that he doesn’t know might be the film’s most damning detail.)

The limo driver, gay costumer, supermarket owner – all bring over-the-top, believable chaos. Even a single-line bit from “the stuntman” lands perfectly, escalating an already bizarre sequence.

Final Notes

The last scene, featuring The Big Three on Jimmy Kimmel Live, closes the loop with one final prank. It’s easy to understand why Kimmel has since distanced himself from the film. Its content feels misaligned with Kimmel’s current image.

The editing is jagged. The production, shoddy. But for a prank film made in the early 2000s – with cameras trying to capture unpredictable chaos – it’s admirable how much they pulled off.

Verdict

Windy City Heat is an artifact. If you’re interested in cult comedy, deep cringe or the limits of practical performance – this film belongs on your syllabus. Everyone else can skip it without guilt.

★★★★★

For briefer takes check: IMDb & Letterboxd.

For a better free-to-stream The Transformers: The Movie.