Jon DulaNew Jersey Film Connection

Films Set In Chicago and Cleveland Posted on 2016-10-25 by Jon Dula

In honor of the World Series, today I will be making my prediction of the outcome based on which city has better films set and/or filmed in their area. Which city has better films, Chicago or Cleveland? This goes completely against my usual predictions because of my 20 years of experience watching baseball and my thirteen years playing but that dream is long gone therefore I'll take a screenwriter's approach to predicting the World Series this year.

Films Set or Filmed In Chicago

Chicago is definitely more driven by entertainment than Cleveland therefore more films have come out of Chicago. I guess I'll have to give Chicago points for that. Okay let's get started...

"The Hunter" (1980)

The first film on my list is Steve McQueens's last film. Of course this film made my list specifically because of the famous chase scene which has become iconic through the years.

"Sixteen Candles" (1984)

A John Hughes classic that captures the beauty of Chicago along with the strong teen characters that began John Hughes' reign of the 1980s.

"The Untouchables" (1987)

A film about ganster icon, Al Capone, deserves its place on this list with a star-studded cast including Sean Connery, Kevin Costner, and Robert DeNiro.

"North by Northwest" (1959)

An Alfred Hitchock classic that includes some of Chicago's most well known areas including the Ambassador East hotel and the LaSalle Street Station.

"Home Alone" (1990)

This hilarious family film shot child actor McCauey Calkin into super-stardom. But his career has followed the trend of Chicago, meaning both are much less appealing nowadays than they were in the 90s.

"High Fidelity" (2000)

A personal favorite of mine. This film captures what it is like to live in Chicago and the types of people that lived there in the 90s and early 2000s. John Cusack delivers one of his better performances and an almost unknown Jack Black becomes the Jack Black we've come to know and love nowadays.

"Ferris Bueller's Day Off" (1986)

Another John Hughes classic finds its way into the equation and if this isn't one of your favorite 80s films then I don't believe you. Ferris Bueller and his gang explore everything that makes Chicago the city it is. This fun and hilarious film makes Chicago tough to beat.

Films Set In or Filmed In Cleveland

"Major League" (1989)

This film gives Cleveland bonus points for being a comedy classic and for involving the Cleveland Indians. Although I did exclude "Rookie of the Year" which involves the Chicago Cubs, it does not live up to the standards of this film.

"A Christmas Story" (1983)

One of the most recognized and quotable Christmas films of all time definitely deserves recognition. A film that is aired for twenty-four hours straight one day a year is nothing short of a classic.

"The Deer Hunter" (1978)

Though this film is set in the Pittsburgh area, it was shot in Cleveland's Tremont neighborhood. The cast of this film is legendary just as the film is itself.

"Happy Gilmore" (1998)

One of the classic Adam Sandler films from the 1990s was largley filmed in and around Cleveland. Comparing the two lists as they stand at the moment. Cleveland seems to have Chicago beat in regards to comedy.

"American Splendor" (2003)

This Oscar-nominated film starring Paul Giammati definitely deserves to be mentioned. I may be a little biased because of its nomination for Best Adapted Screenplay but I think it is a very good film nevertheless.

"The Avengers" (2012)

This film became an instant classic after shattering records at the box office. Most of the film was filmed in Cleveland and gives Cleveland a very big boost in this competition. None of the films from Chicago have achieved the monetary success The Avengers did.

"Spider-Man 3" (2007)

Before there was The Avengers, there was Spider-Man 3 which made Cleveland look like it was New York City. Though not the best Spider-Man film, it still was very successful in the box office upon its release.

Okay after seven slected films from each city (seven for a seven game series) I have come to a conclusion.

And The Winner Is...


In terms of film and entertainment, Cleveland was an underdog since Game 1. Chicago has given us more than a handful of classic films and hopefully can be restored to the city that gave us these films in the first place.






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