Here’s my most powerful Chicago movie moment: I was producing the Friday film forum for Odyssey, the now-defunct WBEZ “daily talk show of ideas.” The topic: movies about serial killers. As preparation I decided to revisit the 1986 John McNaughton flick Henry: Portrait of A Serial Killer. I didn’t have a TV, so I headed over to my friend Chris Natali’s house, at the corner of Wood Street and North Avenue. Now I’d seen the film before, as an undergrad. But I didn’t remember - or hadn’t noticed - it was a movie made in Chicago.

So there we were, nestled into the couch, namechecking some of the settings. The corner of Paulina and Milwaukee in Wicker Park, decked out in now mostly gone neon finery. The Picasso statue in Daley Plaza. The eerie, greenish space of Lower Wacker Drive. Then suddenly, a far-too-familiar landmark appeared: The (then) pink-tinged sign for the local exterminator shop, Rose Pest Solutions. The shop was literally a door or two down from the entrance to Chris’ apartment. And as we pieced together what had looked like unknown terrain we realized that the apartment shared by Henry and his roommates, brother and sister Otis and Becky, must be just around the corner - literally behind - Chris’ building. Talk about cinema vérité! The already creepy low budget thriller had become a gritty, quasi-documentary we just wanted to turn off.

That’s part of the power of movies shot in your hometown - they make you see everyday scenes in an entirely different (and not always flattering) light! Thanks to recent screenings and an imminent DVD release, many Chicagoans are now re-discovering the long-forgotten 1978 film Stony Island, shot on the South Side and directed by Andrew Davis of Fugitive fame. So it seems like a good opportunity to revisit some of my favorite made in Chicago movies. Though there are more recent Chicago films I really enjoy - from The Break-up to The Dark Knight - I’m going a bit old school with my picks. Educate me - add your favorite Chicago movies below!

(A warning: This scene contains graphic violence)

1. Henry: Portrait of a Serial Killer. Mid-1980s Chicago looks seedy but intriguing, still a work-a-day town full of low-rent pursuits of both the business and pleasure type. Henry introduces Otis to his killing ways after picking up a couple of ladies of the night on Clark Street, right in front of a #22 bus! After seeing this film again I’ll never feel entirely safe on my short-cut through Lower Wacker Drive.

On the other hand, I’ll be very sad if the current rehabilitation of that thoroughfare erases its chilly, mysterious vibe, which derives at least in part from its appearance in Henry (it is somehow fitting that Daniel Burnham’s utopian vision is an equally suitable setting for Henry’s dystopic dreamworld). Other Chicago credentials: The film is directed by local John McNaughton (his film Wild Things is one of my not-too guilty pleasures) and was a big break for baby-faced actor Michael Rooker, who developed his acting chops here.

The opening scenes of Cooley High

2. Cooley High. I don’t get why so many people don’t like this movie. Sure it’s got a fairly episodic structure - but I think that kind of reflects the mercurial, distracted and itching-to-be-adult mindset of its young protagonists. Set in 1964 but shot in the ’70s, Cooley High captures that particular stance I think of as Chicago cool. Point guard Derrick Rose has got it. Our former Mayor Daley - for all his red-faced outbursts - has got it. Only here we’re not talking about the players who inhabit the heights of Chicago power, but the sons and daughters living on one of the bottom rungs, in the now-defunct public housing project Cabrini-Green (the school was also razed and replaced by Near North Career High School). The director Michael Schultz hails from Milwaukee - and worked with many actors from the New York theatre scene (especially the Negro Ensemble Company). But Chicagoan Robert Townsend makes his film debut in Cooley (a very small cameo). And the city represents - from Lincoln Park Zoo (they hitch a ride there on the back of a CTA bus) to Burr Oak cemetery. As my friend Damon Locks notes, the only thing missing is a Chicago-centric soundtrack: Schultz went Motown when he could have featured Chicago soul music to great effect.

The famous coffee shop scene, where James Caan makes Tuesday Weld an offer she can’t refuse

3. Thief. Oh I could write about this movie for days. Truly great performances from Tuesday Weld and James Caan. The tragic narrative arc of the (somewhat) honorable thief, whose last big score proves to be a major bust. Like all my other choices, there’s no happy ending on hand here. But this is a movie to swoon over. It is native son Michael Mann’s feature debut and he deploys a quintessential but easily overlooked Chicago setting - a small car dealership along Western Avenue. Powerhouse local talents, including James Belushi, Dennis Farina and William Petersen appear, the latter as a bartender in the - yes, now-gone - north side club Katz & Jammer. Mighty Joe Young and band plays in that scene. Thankfully Caan didn’t actually blow up The Green Mill! Now, most of the music is as far from Chicago as you can get - the soundtrack is composed by German electronic group Tangerine Dream. And yet it works. Like Henry and Cooley, this is a highly influential and oft-referenced film. If you don’t believe me, settle down for back-to-back viewings of Thief and last year’s Drive, starring Ryan Gosling (the 21st century internet meme/poor-man’s version of James Caan?). Oh, and if you’re a fan of the Dream, their tour this summer includes a stop in Chicago - at the Vic on July 18.