Windy City Heat (2003)

Having taken some time to re-watch and ruminate over Windy City Heat (I’ve seen it four times and counting), explaining the enduring appeal of it is still tricky. First of all, it’s funny. It’s blindingly funny. It’s tip a cow then kick a duck up the arse funny. It’s also fantastically original in it’s conception and treads heavily where few might dare to tread at all.
The mark in this; possibly the most elaborate prank ever, is the fabulous Perry Caravello. Arrogant, sexist, homophobic and gullible. He is hilariously short tempered yet naive and lovable. Our catalysts and instigators are Don and Mole who according to the film have been messing with Perry for over a decade now.
The setup is to have Perry, an aspiring actor and comedian in Hollywood, audition for a part in a film and win it. They go on to shoot the actual film over the course of a week, only it’s all part of the setup and every scene is just another opportunity to provoke Perry’s wrath while the cameras are rolling. There is physical comedy, humiliation, and provocation. It’s great.
When watching the film you will recognise names and faces. The in-jokes are endless. Perry gets none of the references. I do get twinges of pity for Perry as he falls for joke upon joke. Half the jokes are just to sell or justify a previous joke or fabrication. Some of the setups seem so contrived that it’s hard to believe anyone would fall for it, but Perry sees no problems.
It’s humour is maybe a little cruel and sadistic in spirit, which in turn provokes thought on edgy comedy as an elaborate web of ethical dilemmas. Fortunately, any uncomfortable doubts about what you’re watching are put to bed when you understand the relationship of Perry with Don and Mole. Perry is working, making some money and gaining the fame his so craves. Though it’s clear someone like Perry can be (and has been!) taken advantage of in a town like Hollywood, I’d go as far to say Perry is protected by Don and Mole and there’s obviously some affection there.
The underlying fascination of WCH has percolated to the depths of my subconscious and left me quite frankly, obsessed. If there were ever a film cult I was part of than this is it. It is continued now with the excellent ongoing podcast (The Big Three podcast) and the unfolding drama and windups over facebook and other online forums.
WCH triumphs where a film like I’m still here totally failed. There is no holier than thou Hollywood smugness. It is well planned and improvised and thick with gags from the most base to the marvellously subtle. It runs hand in hand with An idiot abroad as the most hilarious and startlingly real tragi-comedy out there. Comedy on film is often about levity and escapism but on the other end of that spectrum lies WCH, something that’s real and engaging, provocative and most importantly, deeply and lastingly funny.