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For the first two installments of this Virtual Culture Trip series, we sat on the dock of the Bay in San Francisco and got welcomed to the jungle in Los Angeles. Today, let’s ditch the West Coast for the Gold Coast, and drop onto the shore of Lake Michigan and into “Sweet Home Chicago.” The Second City’s stories grow from the immigrants and migrants who came to work in the slaughterhouses and stockyards and factories near the ocean-wide lake, and the amazing architecture has created a scenic backdrop that filmmakers return to again and again. As the great actress Sarah Bernhardt said, “I adore Chicago. It is the pulse of America.”
The standard caveat applies: This isn’t a definitive list; rather, it’s a collection of books, movies, and songs that take my mind to the Windy City. I hope they do the same for you.
1. The Jungle by Upton Sinclair
Ah, the book that inspired a million vegetarians. Muckraking journalist Upton Sinclair spent several weeks in 1904 working in Chicago’s meatpacking plants, publishing his account first as a newspaper serial and then, in 1906, as a novel. Sinclair, an avowed socialist, meant for the book, which described the horrific working and living conditions endured by laborers, to advance his political beliefs. Instead, it ended up leading to the passage of federal food safety laws and, ultimately, the establishment of the FDA. “I aimed at the public’s heart,” the author once said, “and by accident I hit it in the stomach.”
2. Native Son by Richard Wright
Richard Wright’s landmark 1940 book is, along with Ralph Ellison’s Invisible Man, the foundational novel of African American literature. Native Son tells the tale of a young black man, Bigger Thomas, who is drawn into a life of crime amid the poverty of 1930s South Side Chicago and is ultimately sentenced to death for committing a pair of murders. While some critics, including the great author James Baldwin, have called the book’s protagonist stereotypical, Baldwin also wrote, “No American Negro exists who does not have his private Bigger Thomas living in his skull.”
3. The Adventures of Augie March by Saul Bellow
“I am an American, Chicago born,” begins this 1953 novel, a picaresque tale that follows its everyman hero as he meanders from job to job and lover to lover in Great Depression–era Chicago. Augie March won the National Book Award and is often placed on the short list of candidates for the Great American Novel. Bellow won the Nobel Prize in 1976, and is perhaps the great writer most associated with Chicago, where he lived for much of his life.
4. The House on Mango Street by Sandra Cisneros
Who among us did not read Sandra Cisneros’s touching 1984 coming-of-age novel in middle or high school? The book, a series of vignettes narrated by a 12-year-old Mexican-American girl named Esperanza, is loosely based on the author’s own childhood in a poor, mostly Hispanic neighborhood in Chicago. Few works in literature better express the experiences of a young girl—from childish innocence to sexual awakening—or convey the halting promise of the American dream than does this modern classic.
5. The Devil in the White City by Erik Larson
This 2004 best-seller is an example of truth being stranger than fiction. Erik Larson builds the book around two men—Daniel Burnham, the chief architect of the 1893 Chicago World’s Fair, and Dr. H.H. Holmes, a serial killer who built a grisly “Murder Castle” not fair from the fairgrounds. A Hulu series adaptation, executive-produced by Leonardo DiCaprio and Martin Scorsese, is in the works.
1. The Blues Brothers
“It’s 106 miles to Chicago. We’ve got a full tank of gas, half a pack of cigarettes, it’s dark, and we’re wearing sunglasses. Hit it!” Dan Aykroyd and John Belushi were indeed on a mission from God in this 1980 classic, and that mission was to make one of the most beloved comedies of the 20th century. Aside from its eternally quotable script, its numerous Chicago locations, and its charismatic co-leads, this spinoff of the 1970s Saturday Night Live skit leans on musical numbers led by superstar guests including James Brown, Ray Charles, Aretha Franklin, and Cab Calloway.
2. Ferris Bueller’s Day Off
What movie makes better use of Chicago than this 1986 teen comedy? Director and Windy City native John Hughes said, “I really wanted to capture as much of Chicago as I could. Not just in the architecture and landscape, but the spirit.” Hughes did just that, filming instantly recognizable scenes at Sears (now Willis) Tower, Wrigley Field, and the Art Institute of Chicago. But let’s be real: None of those is as memorable as the parking garage attendants’ joyride in the Ferrari.
3. The Untouchables
Al Capone is perhaps the most famed gangster in American history, and he’s portrayed chillingly by Robert De Niro in this acclaimed 1987 crime film. Director Brian De Palma dramatized the campaign to bring the Chicago crime boss down, working off a screenplay written by Second City native David Mamet, casting Kevin Costner as Eliot Ness, and filming many scenes on location in Chicago. As Oscar winner Sean Connery’s Jimmy Malone says: “He sends one of yours to the hospital? You send one of his to the morgue. That’s the Chicago way.”
4. Hoop Dreams
Great sports movies are about more than sports, and that’s true of this astonishing 1994 documentary. The filmmakers spent five years following two high school basketball players from inner-city Chicago, William Gates and Arthur Agee, as they chased their goal of making it to the NBA. While the nearly three-hour-long doc takes viewers deep into the shifty world of prep basketball recruiting, its most enduring moments have nothing to do with hoops at all, such as when Agee’s father wanders away from his son on the playground to buy drugs, or when Agee’s mother joyfully celebrates her graduation from nursing school. Hoop Dreams is on the short list of the most essential films of the last 30 years.
5. High Fidelity
While Nick Hornby set his hit 1995 novel in London, for the film adaptation, the screenwriters, including star John Cusack (a native of Evanston, Illinois), shifted the setting to Chicago. After breaking up with his girlfriend, Cusack’s Rob Gordon, a DJ who owns a record store in Wicker Park, reviews his romantic history, making musical top-five lists along the way. The supporting cast includes Jack Black (in his big breakout), Catherine Zeta-Jones, Lisa Bonet, and a memorable cameo from Bruce Springsteen. As an aside, Chicago wasn’t High Fidelity’s last stop from London: This year, Hulu aired a series adaptation, starring Zoë Kravitz (Bonet’s daughter, in a smart bit of casting) and set in Brooklyn.
Risky Business (you’ll never look at the “L” train the same way); Christmas Vacation (Hollywood loves setting Christmas movies in the Chicago suburbs—see also, Home Alone); Backdraft (Ron Howard’s firefighting thriller turned the Brighton Park firehouse setting into a landmark); The Fugitive (an absolute classic set in and around the city); Chicago (this 2002 musical won six Oscars, including Best Picture).
1. “Sweet Home Chicago” by Robert Johnson
Chicago was one of the primary endpoints in the Great Migration, which saw millions of African Americans leave the South to escape Jim Crow oppression and search for economic opportunity. Among the cultural impacts of this diaspora was the spread of the blues. Mississippi’s Robert Johnson is widely considered the most influential of the Delta blues musicians, and he recorded this standard in 1936, less than two years before his death at the age of 27. (Legend has it he was poisoned by a jealous husband.) The song has since become an anthem for the Windy City.
2. “Rollin’ Stone” by Muddy Waters
McKinley Morganfield was born in Mississippi, but in 1943 he moved to Chicago to become a musician, performing under the name Muddy Waters. He began playing electric guitar and soon became a recording star for the groundbreaking Chess Records. The electric blues remains Chicago’s signature sound, and Muddy Waters is often referred to as the father of the style. He would go on to be imitated not only by other bluesmen but also by the rock stars of the 1960s, including a group of young British lads who named their band after this 1950 hit. You may have heard of them.
3. “Hello in There” by John Prine
A native of suburban Maywood, Illinois, John Prine spent part of his early 20s working as a mailman in Chicago. He wrote songs in his head while walking his route, and soon he began performing at open mics. (A young Roger Ebert wrote Prine’s first review.) The rare mix of humor and empathy Prine displayed made him one of America’s most beloved songwriters; his 1971 self-titled debut album is a murderer’s row of classics, among them “Angel from Montgomery,” “Paradise,” “Sam Stone,” and this song, told from the perspective of a lonely old person who’s just waiting for someone to stop and say hello. Prine died earlier this month, at the age of 73, from COVID-19. If you don’t know his work, it’s worth your time to stop and introduce yourself. RIP John.
4. “Via Chicago” by Wilco
While Jeff Tweedy is actually from a suburb of St. Louis (Belleville, Illinois), the Wilco frontman has made Chicago his home for the better part of two decades. During that time, the band, which grew out of the ashes of the revolutionary alt-country act Uncle Tupelo, became one of the most acclaimed rock groups in America. This song, from the 1999 album Summerteeth, has such a lilting, soothing sound that it’s easy to miss to that it could be interpreted as a murder ballad—its opening line, after all, is “I dreamed about killing you again last night.” What I take away from the song is more that Chicago is the hub of the entire Midwest, and no matter what route you imagine taking when you think of going home, you’ll probably need to go “Via Chicago.”
5. “Homecoming” by Kanye West
Things got a little, um, weird with Kanye over the last few years, but that doesn’t change his status as probably the most influential rapper of the 21st century. This single from the 2007 smash-hit record Graduation is West’s shout out to his hometown (while he was born in Atlanta, he moved to Chicago at age 3 and grew up there). While the hook is sung by a rock star who’s definitely not from Chi-town—Coldplay’s Chris Martin—the metaphorical lyrics and pop-friendly production are pretty much peak Kanye.
“I’ll Take You There” by The Staples Singers (we all could use a little more Mavis Staples in our lives); “I’m Every Woman” by Chaka Khan (Whitney Houston got a Grammy nomination for her cover of this song, but the original was performed by Chciago’s own funk goddess); “A Dying Cubs Fan’s Last Request” by Steve Goodman (no Chicago list is complete without a paean to the misery of pre-2016 Cubs fandom); “Today” by Smashing Pumpkins (how many speakers have the fuzz-laden guitars on Siamese Dream destroyed?); “I Used to Love H.E.R.” by Common (Chicago’s first superstar MC drops a metaphorical riff on the commercialization of hip hop). And for even more Chicago songs, check out the full playlist.