One of the subjects we’ve been deeply fascinated with at The TRiiBE is the way Chicago’s history is depicted in film. Through our reported stories and The TRiiBE Guide 2021, we’ve learned that during the early 20th century, when Chicago was considered the Black Metropolis, the film and theater industries were thriving here. 

Unfortunately because of targeted disenfranchisement and the persistent subjugation of Black folk in Chicago, we’ve lost most of that industry. Regardless, Chicago has remained a cultural hub for Black America and continues to host many of cinema’s most compelling Black narratives. 

For this list, TRiiBE reporter Matt Harvey parses through some of Chicago’s most iconic placements in Black cinema and ranks them based on how accurately and creatively they depict Black Chicago.

8. Judas and the Black Messiah (2021)

BRON Studios

Director: Shaka King

Writer: Kenny Lucas, Keith Lucas

“Judas and the Black Messiah” is the Lucas brothers’ treatment of the much-too-short life of revolutionary Chairman Fred Hampton from the perspective of a mole who infiltrated the Illinois Black Panther Party. While the filmmakers aren’t super intentional about how they depict the movie’s Chicago setting, it makes it onto the list because it is the best attempt that’s been made at telling what is undeniably one of the most important stories in the history of Black Chicago. Chairman Hampton packed a lot of living, learning and organizing into his 21 years, so trying to fit it alongside a crime drama is hard to pull off, but the Lucas brothers make a solid effort here.

7. Southside with You (2016)

Get Lifted Films/IM Global

Director: Richard Tanne

Writer: Richard Tanne

There’s something about a romance movie that just does a great job of letting viewers admire the setting. Richard Tanne’s “Southside With You,” which tells the story of Barack and Michelle Obama’s first date in 1989, has only one co-star alongside Tika Sumpter’s Michelle and Parker Sawyers’ Barack— and that’s Hyde Park. Given that Hyde Park is being aggressively gentrified around University of Chicago and now, ironically, the Barack Obama Presidential Center, “Southside With You” is a refreshing walk down memory lane to a time when the whole out South was just as unflinchingly beautiful and Black as you could fathom.

6. Roll Bounce (2005)

State Street Pictures/Fox Searchlight

Director: Malcolm D. Lee

Writer: Norman Vance Jr.

Man, ain’t “Roll Bounce” just fun to watch? It’s the only movie on the list I had to run back one extra time just to feel all tingly inside again when the crowd cheers on Bow Wow’s character Xavier “X” Smith after his admirable attempt to dethrone Sweetness (played by Wesley Jonathan) in the roller disco contest. With “Roll Bounce,” writer Norman Vance Jr. and director Malcolm Lee manage the tightrope act of making a movie that feels real, but never serious. Although the names and lore of the rinks in the film don’t exist in real life (Sweetwater scenes are filmed at a roller rink in Lynwood, Ill., and the Palisades shots are filmed in a rink in Summit, Ill.), it treats roller skating with all the severity of real life on the South Side in the late 1970s.

5. Love Jones (1997)

Addis Wechsler Pictures 

Director: Theodore Witcher

Writer: Theodore Witcher

I’m not a big romance movie guy, but if I didn’t have this one on the list, I’d be dragged by every hopeless romantic who ever thought they’d find the love of their life at a poetry slam. Jokes aside, cinematographer Ernest Holzman did his thing framing Chicago in such a romantic way that you find yourself falling for Nia Long and Larenz Tate’s Nina and Darius as they meander through Grant Park, and step at the Blackstone Hotel. “Love Jones” is writer/director Theodore Witcher’s love letter to Chicago and it’s delivered as beautifully as any of the poems shared throughout it’s runtime.

4. Candyman (1992)

PolyGram Filmed Entertainment/Propaganda Films

Director: Bernard Rose

Writer: Bernard Rose, Clive Barker

Let’s get one thing out the way — Candyman is real. Now that we’ve got that cleared up, let’s dive into why it is, exactly, that this statement rings true for so many of the Chicagoans who’ve seen the movie. The film’s protagonist, Helen Lyle, is a University of Chicago grad student who sets out to study the way residents of the Cabrini-Green housing projects use the folklore of the Candyman to cope with hardship —but soon finds out just how real it is. The reason why the Candyman is real for Black Chicagoans is that the circumstances that created him are real. When we watched the film and saw its depictions of life in the Greens, the intense poverty, dilapidated housing and innocent people dying, that part was anything but folklore. Candyman might not be the most beautiful depiction of Black life in Chicago, but it is the most frighteningly realistic.

3. Soul Food (1997)

Fox 2000 Pictures/Edmonds Entertainment Group

Writer/Director: George Tillman Jr.

Few films have achieved Black ubiquity to the degree that George Tillman Jr.’s “Soul Food” has. In addition to the outstanding writing and directing effort Tillman lends to his major studio debut, the star-studded cast includes Nia Long, Vanessa Williams, Mekhi Phifer, and Vivica A. Fox delivering stellar performances. “Soul Food” succeeds where many fall short by creating the image of a Black family that is made up of human characters rather than a family that serves as a vehicle for depicting struggle. “Soul Food” is as much a cultural institution as it is a movie.

2. Barbershop (2002)

Cube Vision/MGM/State Street Pictures

Director: Tim Story

Writer: Mark Brown, Don D. Scott, Marshall Todd

“Barbershop” is the type of movie that we all low-key knew we wanted, but didn’t know exactly how much we needed. By telling the story of Calvin (Ice Cube) and the day-to-day grind of running his late father’s South Side barbershop, the filmmakers are doing the invaluable work of turning the intimate, communal experience of the shop into a universal one. When you walk into the barbershop, you might have on your mind whether you finna mix up your style, or what folks are thinking about yesterday’s game, or what bad music takes might cause an uproar. What you don’t necessarily consider is that in every hood in America, someone else is walking into their local shop thinking the same exact things. Their success in making a film with such an overtly Chicago essence is rivaled only by “Soul Food,” whose writer/director George Tillman Jr. contributed to “Barbershop” as a producer. What Barbershop did was invite everybody who’s shared that experience into the same shop, and what better place for that shop to be than the South Side of Chicago.

1. Cooley High (1975)

American International Pictures/Cooley High Services Company

Director: Michael Schultz

Writer: Eric Monte

My entire life, I’ve been enamored with the stories of my elders’ childhood. During family functions growing up, you might have caught me ear hustling the grown-ups table as my mom, aunties and uncles took strolls down memory lane. I don’t really recall all the particulars of what media they took as their favorites of the time, but one thing never escapes me; their unanimous love of “Cooley High.” With the backdrop of screenwriter Eric Monte’s real-life alma mater, the now-closed Cooley Vocational High School, once located on the Near North Side, the movie is a photorealistic depiction of Black adolescence in 1960s Chicago. It follows best friends Preach and Cochise through citywide misadventures such as skipping school, shooting dice, chasing girls and joyriding. Monte doesn’t have to reach at all to depict something resembling reality, since he lived it. And it goes beyond the plot. 1960s Chicago shows in everything from the set design, to the costuming, to the casting (my momma grew up next door to Pooter a.k.a Corin Rogers). “Cooley High ” is the closest I’ve come to truly visualizing the world my elders describe in their anecdotes and is the most well-rounded depiction of Black Chicago I’ve ever seen on film.

is a staff writer with The TRiiBE. Email him with news tips.