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Chicago in Pop Culture

@chicagopopculture.bsky.social

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Chicago represented in pop culture. Large focus on non-local interpretations of the city. Extended credit included in alt text. No AI.

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Chicago in Pop Culture @chicagopopculture.bsky.social · 09/10/2026

Mike Ditka (1960s)

Vintage black-and-white 1960s advertisement featuring Chicago Bears tight end Mike Ditka, wearing his No. 89 uniform, dramatically catching a football with one leg raised high in the air. The headline reads “THE MUSCLES...” A caption identifies Ditka as 6-foot-3, 230 pounds and one of football’s most punishing blockers. Hill-Behan Lumber Co. appears as the sponsor at the bottom.

Chicago in Pop Culture @chicagopopculture.bsky.social · 30/09/2026

Damen Silos during filming of Transformers: Age of Extinction (2013)

Demolition of the Damen Silos in Chicago, with controlled explosions blasting through the massive concrete grain-elevator structures as dust and debris erupt outward; a green boom lift stands at left.

Chicago in Pop Culture @chicagopopculture.bsky.social · 29/09/2026

The Mighty Thor (1983)

Comic-book splash page from The Mighty Thor showing Thor flying above Chicago with Mjolnir raised, his red cape sweeping dramatically behind him. The page announces “The Coming of the Crusader!”
Credit: The Mighty Thor #330 (1983). Art by Alan Zelenetz, Bob Hall, and Vince Colletta.

Chicago in Pop Culture @chicagopopculture.bsky.social · 29/09/2026

The Chicagoan (1929)

Nat Karson. The Chicagoan magazine cover dated October 26, 1929, with a black background and bold lime-green title lettering. A stylized Art Deco football player in a helmet and uniform lunges dramatically over a stadium, rendered in vivid yellow, red, orange, green, and pale blue lines. Tiny marching-band figures appear below, with “Price 15 Cents” printed at the upper right.

Chicago in Pop Culture @chicagopopculture.bsky.social · 29/09/2026

Chicago Bears program (1930)

1930 Chicago Bears football program cover featuring a blue bear bursting through a large gold football, flanked by two small uniformed figures. Red and blue lettering reads “Official Program,” “1930,” “Chicago Bears Football Club Inc.,” “Wrigley Field,” and “Price 10¢,” framed by a wavy red-and-blue border.

Chicago in Pop Culture @chicagopopculture.bsky.social · 18/09/2026

Conan O'Brien gifting Taylor Tomlinson American Girl dolls. Water Tower Place (2019)

Conan O’Brien and Taylor Tomlinson stand beside a decorated Christmas tree in Chicago, each holding an American Girl doll during a 2019 Conan segment.

Chicago in Pop Culture @chicagopopculture.bsky.social · 18/09/2026

Dick Gregory (1965)

Dick Gregory marches in Chicago in 1965 holding a sign reading “DALEY EDUCATION COMES FIRST,” during protests over school segregation. Credit: Chicago Sun-Times collection, 1965.

Chicago in Pop Culture @chicagopopculture.bsky.social · 17/09/2026

Michigan Boulevard at Night, Postcard (1911)

Michigan Boulevard at Night, Chicago, 1911, published by V. O. Hammon Publishing Co., Chicago. Colorized postcard showing Michigan Boulevard bustling with early automobiles and pedestrians beneath glowing streetlights, with Illinois Central’s Central Station and illuminated buildings in the background near Grant Park.

Chicago in Pop Culture @chicagopopculture.bsky.social · 16/09/2026

The Chicagoan (1930)

Cover of The Chicagoan, March 29, 1930, featuring a stylized overhead illustration of Chicago’s lakefront and roadway system, with streams of automobiles, boats, landscaped areas, and streetlamps rendered in colorful Art Deco–era graphics. The Chicagoan, March 29, 1930; courtesy of the University of Chicago Library.

Chicago in Pop Culture @chicagopopculture.bsky.social · 15/09/2026

Absolut ad (1990s)

Absolut Chicago, c. 1990s. Absolut Vodka advertisement showing a bottle against a dramatic black-and-white backdrop, with its blue label letters blowing away to the right in a playful reference to Chicago’s “Windy City” nickname. “ABSOLUT CHICAGO.” appears prominently below. Advertisement by TBWA; digitally restored/edited.

Chicago in Pop Culture @chicagopopculture.bsky.social · 15/09/2026

Franklin D Roosevelt, Democratic National Convention (1932) Chicago Stadium

Franklin D. Roosevelt raises his fist while addressing delegates at the 1932 Democratic National Convention inside Chicago Stadium in Chicago, 1932. NBC and Columbia Broadcasting System microphones stand before him as delegates and flag bearers crowd the platform. Credit: photographer unknown.

Chicago in Pop Culture @chicagopopculture.bsky.social · 14/09/2026

Married with Children (1987)

Buckingham Fountain sprays water in the foreground of a hazy Chicago skyline in the opening credits of Married... with Children (1987–1997), with the CNA Center visible at right.

Chicago in Pop Culture @chicagopopculture.bsky.social · 13/09/2026

The Super Bowl Shuffle, Chicago Bears Shufflin’ Crew.

1985 promotional image for The Super Bowl Shuffle, showing members of the Chicago Bears Shufflin’ Crew posing and dancing in Bears uniforms against a white background. Walter Payton (#34) stands prominently at center, surrounded by teammates including Willie Gault (#83) and Mike Singletary (#50). Bold text above reads “THE SUPER BOWL SHUFFLE” and “THE CHICAGO BEARS SHUFFLIN’ CREW.” Photo: Paul Natkin/Getty Images.

Reposted by Chicago in Pop Culture

Chicago in Pop Culture @chicagopopculture.bsky.social · 22/08/2026

Red title card with bold white lettering reading “MIDNIGHT IN CHICAGO” and, below it, “EVERYONE.”

Chicago in Pop Culture @chicagopopculture.bsky.social · 12/09/2026

All-Star Program, Wrigley Field (1962)

1962 All-Star Game souvenir program cover for Wrigley Field in Chicago. A bold mid-century modern illustration depicts a baseball player swinging a bright yellow bat, rendered in angular geometric shapes of red, blue, gray, black, and white. Red lettering across the top reads “ALL STAR SOUVENIR PROGRAM 50¢,” while blue text along the bottom reads “WRIGLEY FIELD · CHICAGO 1962.”

Chicago in Pop Culture @chicagopopculture.bsky.social · 12/09/2026

The Bear (2022)

Jeremy Allen White as Carmen “Carmy” Berzatto stands on a Chicago bridge at night in The Bear (2022), framed from behind beneath two glowing yellow streetlights, with the wet roadway and downtown buildings stretching into the distance.

Chicago in Pop Culture @chicagopopculture.bsky.social · 11/09/2026

U2, Chicago, 1981.

U2—Adam Clayton, Bono, Larry Mullen Jr. and the Edge—walking along a downtown Chicago sidewalk in 1981 during the Boy era, photographed in black and white by Adrian Boot.

Chicago in Pop Culture @chicagopopculture.bsky.social · 10/09/2026

Jimmy Corrigan: The Smartest Kid on Earth (2000)

A sequence of panels from Chris Ware’s Jimmy Corrigan: The Smartest Kid on Earth (2000) depicts a quiet Chicago neighborhood beneath the distant Sears Tower, followed by views through a window of a red telephone ringing on the sill. Artwork by Chris Ware.

Chicago in Pop Culture @chicagopopculture.bsky.social · 10/09/2026

Muhammad Ali, Chicago (1966).

Muhammad Ali stands on a downtown Chicago sidewalk in 1966, photographed from a low angle against the towering buildings of the Loop. Black-and-white photograph by Thomas Hoepker / Magnum Photos.

Chicago in Pop Culture @chicagopopculture.bsky.social · 10/09/2026

The Chicagoan (1926)

Cover of The Chicagoan, July 15, 1926, showing a stylish couple overlooking Chicago’s lakefront at night beneath an orange crescent moon and stars, with the skyline and Lake Michigan in the background. Art Deco illustration in blue, orange, black, and white.

Chicago in Pop Culture @chicagopopculture.bsky.social · 08/09/2026

Spiderman 2 (2004)

Spider-Man crouches atop a moving elevated train during the climactic train sequence in Spider-Man 2 (2004), filmed on Chicago’s “L” tracks in the Loop. Columbia Pictures / Sony Pictures.

Chicago in Pop Culture @chicagopopculture.bsky.social · 08/09/2026

Chicago Postcard (1953)

Vintage 1953 Curt Teich & Co. illustrated postcard titled “Swell Hotels in Chicago!” showing a smiling tourist lounging atop an enormous suitcase covered with labels for Chicago hotels—including the Drake, Conrad Hilton, Sherman, Shoreland, Blackstone, Edgewater Beach, and others—while an overwhelmed bellhop struggles beneath its weight. Credit: Curt Teich & Co., Inc., Chicago, postcard 3C-H554, 1953.

Chicago in Pop Culture @chicagopopculture.bsky.social · 07/09/2026

Delta Air Lines travel poster. Fred Sweney (1970s).

Vintage Delta Air Lines travel poster for Chicago, featuring stylized views of Marina City, the Sears Tower, Buckingham Fountain, and one of the Art Institute of Chicago’s bronze lions beneath a large “Chicago” title. Artwork by Fred Sweney, c. 1970s, for Delta Air Lines.

Chicago in Pop Culture @chicagopopculture.bsky.social · 07/09/2026

Chicago Municipal Airport, Postcard (1937)

1937 illustrated postcard titled Chicago Municipal Airport—The Center of Air Transportation of the Nation, depicting a futuristic cutaway airplane flying above the runways and hangars of Chicago Municipal Airport, now Midway Airport, with inset scenes showing passengers, crew, baggage, and aircraft operations. Printed by Curt Teich & Co., Chicago; distributed by J.O. Stoll Co., Chicago, no. 155; Curt Teich no. 7A-H725.

Chicago in Pop Culture @chicagopopculture.bsky.social · 07/09/2026

Kuczak Sausage Shop, 1979 — Letter offering homemade sausage for Pope John Paul II’s Chicago visit.

1979 Kuczak Sausage Shop letter offering homemade sausage for Pope John Paul II’s Chicago visit. Credit: Kuczak Sausage Shop.

Chicago in Pop Culture @chicagopopculture.bsky.social · 05/09/2026

Ferris Bueller’s Day Off (1986)

A red Ferrari flies through the air on a Chicago roadway, with the downtown skyline and Sears Tower visible in the background, in a scene from Ferris Bueller’s Day Off (1986). Credit: © Paramount Pictures.

Chicago in Pop Culture @chicagopopculture.bsky.social · 04/09/2026

Cruis’n USA (1994)

Screenshot from Midway Games’ Cruis’n USA (1994), showing a silver sports car racing through the Chicago course beneath elevated CTA train tracks, with an L train passing overhead. Credit: Cruis’n USA, Midway Games, 1994.

Chicago in Pop Culture @chicagopopculture.bsky.social · 04/09/2026

Big Bird (2019)

Big Bird, wearing a bright orange life jacket, stands on the bow of a boat on Lake Michigan with the Chicago skyline behind him, including the Sears Tower at left. Credit: © Sesame Workshop.

Chicago in Pop Culture @chicagopopculture.bsky.social · 04/09/2026

Serengeti: Kenny Dennis III. Jaimie Warren (2014)

Illustrated cover art for Serengeti’s Kenny Dennis III (2014), depicting the mustachioed, sunglasses-wearing Kenny Dennis in a Chicago Blackhawks cap embracing a blonde woman inside a dim, red-lit neighborhood bar. Other exaggerated figures populate the scene, including a man using a pay phone and a woman seated at the bar. Credit: Cover artwork by Jaimie Warren; Serengeti, Kenny Dennis III, Joyful Noise Recordings, 2014.

Chicago in Pop Culture @chicagopopculture.bsky.social · 04/09/2026

Late Night with Conan O'Brien in Chicago, 2006.

Chicago in Pop Culture @chicagopopculture.bsky.social · 03/09/2026

The Chicagoan, February 9, 1929.

Art Deco cover of The Chicagoan magazine, February 9, 1929, illustrated by Cecil Ogren. A stylized Chicago streetscape depicts three top-hatted passengers riding in a vehicle past a traffic signal, framed by geometric skyscrapers, wheels and bold blocks of blue, red, black and cream. **Credit: Cecil Ogren, The Chicagoan, February 9, 1929; Copyright The Quigley Publishing Company, a Division of QP Media, Inc.; digitized by the University of Chicago Library.**

Chicago in Pop Culture @chicagopopculture.bsky.social · 03/09/2026

H. H. Holmes’s “Murder Castle” (World’s Fair Hotel), W. 63rd Street, 1890s.

Black-and-white photograph of H. H. Holmes’s infamous “Murder Castle,” also known as the World’s Fair Hotel, on West 63rd Street in Chicago’s Englewood neighborhood, mid-1890s. The three-story brick building stands along a snowy street beside elevated railroad tracks, with storefront signs visible at street level. Credit: Chicago History Museum/Getty Images.

Chicago in Pop Culture @chicagopopculture.bsky.social · 03/09/2026

Postcard of Chicago O’Hare Airport, c. 1963.

Aerial view of Chicago O’Hare International Airport, c. 1963, showing the terminal complex, aircraft gates, access roads, and vast parking lots filled with cars. In the foreground, a large sign reads, “Welcome to Chicago-O’Hare International Airport — Richard J. Daley, Mayor.” Credit: Penrod Studio, c. 1963; postcard published by Cameo Greeting Cards, Chicago, and printed by Dexter Press.

Chicago in Pop Culture @chicagopopculture.bsky.social · 03/09/2026

Grateful Dead at the Aragon Ballroom, Chicago. July 3, 1970. Daniel Clyne.

Psychedelic 1970 concert poster for the Grateful Dead at Chicago’s Aragon Ballroom, with dripping red-and-yellow lettering above a surreal Daniel Clyne illustration of winged monsters, bats, rocky cliffs, and frightened human figures against a bright blue background.

Chicago in Pop Culture @chicagopopculture.bsky.social · 03/09/2026

The Batman (2022) James R. Thompson Center

Nighttime scene outside Gotham Square Garden in The Batman (2022), with police cars, fire trucks, ambulances, emergency lights, and crowds filling the rain-soaked streets during the flooding and evacuation of Gotham City.

Chicago in Pop Culture @chicagopopculture.bsky.social · 03/09/2026

Major League Baseball Featuring Ken Griffey Jr. Comiskey Park (1998)

Video game rendering of Comiskey Park in Chicago, viewed from behind home plate toward center field, with the White Sox scoreboard, pinwheels, outfield advertisements, and empty blue bleachers beneath a bright blue sky.

Chicago in Pop Culture @chicagopopculture.bsky.social · 03/09/2026

Candyman (1992)

Helen Lyle crawls through a dark passageway at Cabrini-Green, framed inside the enormous open mouth of a menacing mural of Candyman, in Candyman (1992).

Chicago in Pop Culture @chicagopopculture.bsky.social · 02/09/2026

Joe Louis becomes Heavyweight Champ. Comiskey Park, Chicago. June 22, 1937.

Joe Louis walks toward a neutral corner as referee Tommy Thomas counts over heavyweight champion James J. Braddock, who lies on the canvas after the decisive eighth-round knockdown at Comiskey Park in Chicago, June 22, 1937. Louis won by knockout to become heavyweight champion.

Chicago in Pop Culture @chicagopopculture.bsky.social · 02/09/2026

The Horror of Cabrini-Green, Bruce C. Conn, 1975.

Cover of The Horror of Cabrini-Green by Bruce C. Conn, 1975. Against a black background, large white and red lettering surrounds a photograph of a young Black man wearing sunglasses and a green shirt, standing with his arms crossed against a brick wall. The cover describes the book as a young man’s struggle to survive in Chicago’s Cabrini-Green housing project and includes quotations from the Chicago Tribune, Chicago Sun-Times, and Players Magazine.

Chicago in Pop Culture @chicagopopculture.bsky.social · 02/09/2026

Chicago Art Institute. Famous Chicago Attractions postcard series (1953)

Colorful 1953 illustrated Chicago postcard showing an overwhelmed tourist leaving the Art Institute carrying a large modernist painting while surrounded by exaggerated depictions of artworks, including a sword-wielding figure and a snake. A pennant reads “Famous Chicago Attractions,” with bold text below: “Just Visited… Chicago’s Art Institute!”

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

Bojack Horseman (2019) Clark and Lake "L" stop

Still from BoJack Horseman (2019) showing a winter scene at Chicago’s elevated Clark/Lake CTA station. Diane Nguyen, wearing purple earmuffs and a purple jacket, stands among bundled-up commuters on the wooden platform, while Guy, an anthropomorphic bison in a brown jacket, stands near a woman with a blue suitcase. Downtown buildings rise behind the tracks under a bright blue sky.

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

An Evening with Pearl Jam, Emek Golan, July 19, 2013.

Pearl Jam concert poster for Wrigley Field in Chicago, July 19, 2013, illustrated by Emek Golan. A grimacing man in a blue cowboy hat and suit squeezes an oversized yellow mustard bottle onto a Chicago-style hot dog. Bright orange-and-yellow “Pearl Jam” lettering fills the upper right against a dark blue brick background, with mustard splattered across the poster.

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

The Simpsons, S19 Ep 1 (2007).

Marge Simpson stands inside the Simpsons’ home looking toward Homer off-screen and says, “Homer, you smell like Chicago.” disapprovingly.

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

City That Never Sleeps (1953) Belgian movie poster.

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

Kinetic Playground concert schedule, Chicago, 1969.

1969 hand-drawn blue-and-white concert calendar for Chicago’s Kinetic Playground at 4812 N. Clark St., designed by Mark “Twain” Behrens. The poster advertises late-May and June performances including Led Zeppelin, Pacific Gas & Electric, Illinois Speed Press, The Who, Buddy Rich, Joe Cocker and the Grease Band, Vanilla Fudge, Muddy Waters, Rotary Connection, Eric Burdon, the Zombies, Arthur Brown, and the Youngbloods.

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

Chicago Libra, psychedelic promotional poster, c. 1970

Psychedelic Chicago Libra poster, c. 1970, featuring two stylized women amid swirling ribbons of hot pink, yellow, turquoise, purple, and red. Surreal vignettes include a Playboy bunny, cocktail server, skier, sailboat, beer mug, flowers, clouds, and a suited man, with “CHICAGO” and “LIBRA” incorporated into the kaleidoscopic design.

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

Malcolm X Holding Up Black Muslim Newspaper, Chicago. Gordon Parks (1963)

Black-and-white photograph by Gordon Parks of Malcolm X in Chicago in 1963, wearing glasses and a suit and holding up a Nation of Islam newspaper. Its prominent headline reads, “Seven Unarmed Negroes Shot in Cold Blood by Los Angeles Police,” referring to the 1962 LAPD shooting of Nation of Islam members. Another man stands partially obscured behind him.

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

Nightmare in Chicago (1964)

Title card from Robert Altman’s Nightmare in Chicago (1964), with the words “Nightmare in Chicago” in pale yellow lettering against a dark, grainy nighttime background.

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

Tekken — Chicago stage, Namco, 1994 (Playstation)

Screenshot from Namco’s Tekken (1994) showing Kazuya Mishima and Paul Phoenix fighting on the Chicago stage, a nighttime rooftop arena with the illuminated Chicago skyline in the background. The game interface identifies the location as “Chicago.”

Chicago in Pop Culture @chicagopopculture.bsky.social · 01/09/2026

1988 NBA All-Star Weekend Chicago, official event program.

Cover of the official 1988 NBA All-Star Weekend program in Chicago, featuring a stylized black Chicago skyline against a vivid blue background, scattered yellow stars, and a black-and-red basketball suspended overhead. White text reads “NBA All-Star Weekend Chicago” and “All-Star Saturday, All-Star Game, February 6–7, 1988, Chicago Stadium.”