The 10 Totally Best Chicago Movies

October 24th, 2018 by: relatedchicago

THE 10 TOTALLY BEST CHICAGO MOVIES. Yup, most of them are from the 1980’s.

THE 10 TOTALLY BEST CHICAGO MOVIES - Robert Redford on location in Lake Forest Illinois

Robert Redford on location in Lake Forest, Illinois, directing Timothy Hutton in Ordinary People, 1980

Like Rob Gordon, from the comedy High Fidelity (2000,) we love making lists – mostly about Chicago. Rob and his cohorts’ used their “top five lists” to bring some order to a chaotic world, and we get it. We’ve defined a “Chicago” movie, as one that was actually shot in part here, and one that captured the essence of Chicago in some magical way in the process.

But, first – just a little bit of Chicago movie history.

Chicago was the original hub for movie making at the turn of the 20th century, not New York or Los Angeles. Yes, before Hollywood went on to become, well Hollywood, it was Chicago that paved the way – of course. The city was brimming with production companies and filmmakers at the time. It was the start of the silent movie era, and Essanay Studios in particular was one of the earliest and most powerful, producing fifteen short films with Charlie Chaplin, and giving Gloria Swanson her start. But soon – with the birth of the “western,”the industry headed west. Essanay Studios was eventually absorbed by Warner Brothers, and it would be nearly seventy years before a new creative swell in filmmaking would return.

The gigantic success of two movies are largely credited with jump starting that shift; Cooley High (1975,) written by Eric Monte about his experiences coming-of-age in Chicago, (Monte wrote the hit TV shows; Good Times, The Jeffersons and What’s Happening,) and The Blues Brothers (1980.) The latter in particular was considered to have been the catalyst for ushering in a golden age of filmmaking in Chicago during the 1980s. This eventually lead to the rebirth of the “teen movie” and a trove of iconic John Hughes films; from Sixteen Candles (1985,) The Breakfast Club (1986,) Uncle Buck (1988) and Ferris Bueller’s Day Off (1984.)

So here goes part one of our list – It’s all completely speculative – and in no particular order.

The list (part one)


Released 2000; Directed by Stephen Frears ; Screenplay by John Cusack, D.V. DeVincentis and Steve Pink Starring John Cusack, Jack Black, Iben Hjejle, Todd Louis, Lisa Bonet, Tim Robbins

There are probably not many lists about favorite Chicago movies that do not include High Fidelity, and with good reason. Not only does it perfectly capture a Chicagoan man-child having a thirty-something’s identity crisis at the turn of the century, but the movie’s lead, co-screenwriter and producer is hometown golden boy, John Cusack. You see his passion for the city at every turn. The script is based on the Nick Hornby novel about a record store owner with relationship issues. Originally set in London, Cusack moved the story to Chicago and set-up protagonist Rob Gordon’s shop up in a storefront on Milwaukee Avenue. With such insider touches as references to local record labels like Wax Trax! and Touch and Go Records, it’s easy to believe that Rob and his friends were an authentic part of Chicago’s outta sight music scene in the 1990s.

THE 10 TOTALLY BEST CHICAGO MOVIES - John Cusack in High Fidelity

John Cusack in High Fidelity, 2000


Released 1986; Directed by Edward Zwick; Screenplay by Tim Kazurinsky and Denise DeClue Starring Demi Moore, Rob Lowe, Elizabeth Perkins, Jim Belushi

The film, About Last Night, is remembered for aptly reflecting an authentic Chicago-y singles scene; with its’ main characters playing softball on the weekends in Grant Park and hanging out with their pals at Lincoln Park and Division street bars, where you might find their modern-day counterparts today. Demi Moore even put on twenty pounds so she looked more like a “realistic” Chicago gal. Yeah, I know. Anyway, the script was loosely adapted from the 1974 play Sexual Perversity in Chicago, by Chicago scribe, David Mamet, and was first performed at the Organic Theatre Company. Mamet turned down the chance to adapt his drama about a twenty something couple, who fall in and out of love, with the help of their romantically cynical friends, for the screen. Still, the movie version is a moving love story, that went on to show a generation of gen-xers that love could be found in the Chicago bar scene, and even after a one night stand. Trust us, it’s Demi Moore at her very best – plus anything with Elizabeth Perkins is a go!

THE 10 TOTALLY BEST CHICAGO MOVIES - Demi Moore and Elizabeth Perkins About Last Night

Demi Moore and Elizabeth Perkins in About Last Night, 1986


Released 1980; Directed by John Landis; Screenplay by Dan Aykroyd (story) and John Landis Starring John Belushi, Dan Aykroyd

Chicago is first and foremost, the star of the iconic film, The Blues Brothers, based on John Belushi and Dan Aykroyd’s band by the same name. From the films spot on depiction of the bustling late 1970s Maxwell flea market, to the climatic chase sequence that winds through Lower Wacker Drive, there is no doubt that the musical comedy was an homage to the city. It took director, and hometown boy, John Landis, just two weeks to write the script, and the movie soundtrack sounds like Chicago, with music by Aykroyd and Belushi, and tracks by Ray Charles, Aretha Franklin and James Brown, who also appear in cameos. Jake and Elwood’s journey takes them many places, but most iconic is probably the duo’s epic performance of Jailhouse Rock for the prisoners at Joliet prison.

THE 10 TOTALLY BEST CHICAGO MOVIES - Dan Aykroyd and John Belushi Blues Brothers

Dan Aykroyd and John Belushi, Blues Brothers


Released 1980; Directed by Robert Redford; Screenplay by Alvin Sargent Starring, Mary Tyler Moore, Timothy Hutton, Donald Sutherland

This was Robert Redford’s directorial debut, one so good, that no one ever thought of him as “just an actor” again. Based on the 1976 novel, Ordinary People, by then first time author, Judith Guest, try and watch this film to completion without dissolving into a pool of tears – this film invented the term “tear jerker.” Filmed largely on Chicago’s North Shore during the fall of 1979, the scenery of suburban Lake Forest is instantly recognizable for anyone who grew up in the area. The story follows a Chicago family, shattered the accidental death of its older son. The direction by Redford, and acting across-the-board, is simply sublime. Timothy Hutton plays tormented teen, Conrad, who blames himself for his brother’s death and breaks our collective hearts in the process; Mary Tyler Moore got a nomination as his ice-cold mother, who blames him too, and Donald Sutherland, the peacemaker and arguably the true protagonist of the story, is finally forced to see things as they are. Judd Hirsch played the therapist who helps him, and a very young Elizabeth McGovern plays his love interest. The film went on to sweep the 1981 Academy Awards, winning best picture, best director, best screenplay and best actor for Timothy Hutton.

THE 10 TOTALLY BEST CHICAGO MOVIES - Mark Tyler Moore Donald Sutherland Ordinary People

Mary Tyler Moore, Timothy Hutton, Donald Sutherland, Ordinary People, 1980


Released 1994; Directed by Steve James Starring William Gates and Arthur Agee

Filmmakers Steve James, Frederick Marx and Peter Gilbert set out to film a documentary in 1986 for PBS about playground basketball, hoping to shed light on Chicago’s street culture. They ended up shooting for four years, resulting in the 1994 emotional powerhouse, Hoop Dreams. One may not think that a documentary about basketball would have that kind of impact, but we promise you it does. Director Steve James narrowed in on the lives of two young black teenagers, basketball prodigies, Arthur Agee and William Gates, who grew up in Chicago’s housing projects. After they both win scholarships to a suburban high school, their fortunes diverge. One follows the footsteps of St Joe’s favourite son, all-star Isiah Thomas and the other doesn’t make the cut. Considered one of the best films of the 1990s, it was notoriously snubbed by the Oscars, winning best editing and losing out best picture to of all things – Forrest Gump.

THE 10 TOTALLY BEST CHICAGO MOVIES - Arthur Agee Hoop Dreams 1994

Arthur Agee, Hoop Dreams, 1994

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