“Hit And Run Lovers” written by Jack Nitzsche and Buffy Sainte-Marie, vocals by Edie Lehmann
“Trick or Treat” written by Buffy Sainte-Marie, vocals by Brock Walsh
Interesting Dated References: Being single in the early 80s; being sad in the early 80s; Wearing pleated pants in the early 80s; The color taupe; Lowenbrau beer being something you would bring as a gift to a sick friend.
Best Line: “Some dreams just don’t come true.” The one thing about existential yuppies in the early 80s was at least they were realistic. Sentiments like that quote just don’t exist anymore. Now people say delusional shit like, “Jump and the net will appear,” and, “Be happy.” Everyone is full of shit nowadays.
Social Context: For baby boomers who came of age in the late 60s/early 70s (my mom), the late 70s/early 80s were a terribly unhappy place. All their idealism and hopes and dreams were dashed by The Man™, and all their friends had gone in different directions. Life saddled them with responsibilities, disappointing jobs, and unwanted children. Then The Big Chill came out and it gave them something to identify with and a soundtrack to incessantly annoy their unwanted children with.
Summary: After the success of The Big Chill, studios started searching for and financing anything that had a similar formula. Get a bunch of 30-year-olds reuniting, preferably have one of them be dead, add a bunch of meandering soul searching dialogue, and there you go. Windy City pretty much follows this same formula, but uses Chicago to try to differentiate itself.
The movie opens with our thirty-something narrator Danny (John Shea) telling us how disappointing he and all his seven childhood friends are. Then they allude to the obese friend as being “sick.” He’s not sick because he’s obese, he just happens to be that way and also has some type of deathly illness they never even give a name to.
Danny goes to visit his friend Mickey who is a successful club owner. While visiting the club, all the old friends reunite and take photos and talk about their super awesome childhood gang. Grown men who think their teens were awesome are the saddest people in the world and should be avoided at parties and in the workplace unless you want to have your day/night ruined.
Then Danny has a flashback about the time he was a mailman and fell in love with Kate Capshaw. Who on earth would wear white denim jeans when they are moving all of their possessions by themselves in Chicago in what appears to be the middle of summer? Look how dirty her ass is!
Then we’re back to the present. Danny picks up his sick friend from the hospital. That friend’s name is Sol (Josh Mostel, son of Zero Mostel of The Producers fame). Danny brings him to his apartment, which is right next to the Esquire Theatre. I did some investigating and that space is currently a salon.
Through a bunch more flashbacks, we learn Danny is still obsessed with his ex-girlfriend, Emily (Capshaw), and she happens to be getting married to some other guy over the coming weekend. In the flashback they stand in front of The Mort Gibian Bootery, which means they are on Howard Ave., near Ashland, in case anyone cares.
Sick Sol gets all his friends together for some type of all-night drunken bender that includes going to a frat house, riding around in a limo talking about how they didn’t meet their potential, and attempting to get on a sailboat at like 6 am. Drinking all night until morning with a bunch of people is miserable and nothing meaningful or important ever happens. If you think staying up all night is in any way fun or enjoyable, then you are a delusional and boring person.
So Sol gets even sicker. I really don’t understand why they aren’t naming what disease he’s sick with. Through a bunch more flashbacks we see why things didn’t work out for Danny and Emily, and eventually he tries to reconcile the relationship.
Without much effort or coordination, there is a giant Halloween party at a massive club and all the friends and Emily are there. Danny and Emily kiss. The next day she gets married in a terrible scene that tries to pay tribute to The Graduate. Instead of being upset, Danny focuses all his energy on playing football and convincing his friends to take Sol on a boat to die.
Then Sol dies on said sailboat (which is called The Lindo and is still in operation today under a different name). We flash forward many years and see Danny running into Emily in a grocery store. She is divorced and they pick up right where they left off. As an aside, at one point Mickey does cocaine at the party and nobody even bats a fucking eye. It’s like he’s smoking a cigarette. That shit was so casual back then.
I should mention that one of the friends (Bobby) is played by Jeffrey DeMunn who played Dale on The Walking Dead. That’s him in the lower left of the cast photo. Windy City was written and directed by Armyan Bernstein who went on to become an Executive Producer on a bunch of stuff (Dawn Of The Dead, Children of Men), but it looks like he gave up on the writing/directing after this and the 1987 Martin Short vehicle Cross My Heart. Overall, Windy City isn’t terrible. It’s all acceptable, but the world has past it by. Nowadays no one cares about what 30-year-old adults were worried about in the early 80s. All the world cares about now is teenage girls.
Poster and Box Art: This is a fairly well done illustration. The faces actually look like the actors, and the color treatment overall is so khaki and yuppie it’s awesome.
Availability: Used VHS on Amazon.