As any music nerd who spends a lot time thinking about the following can tell you, both physical and cultural geography have a profound influence on creating and performing music. In the case of Chicago, its presence as the largest city in the Midwest has provided an interesting context for many noteworthy songs penned about the city, not to mention some great music by adopted, temporary and life-long Chicagoans.
For this post, I’ve compiled my favorite 30 songs that are either about Chicago or performed by musicians who have spent a significant amount of time living here.
*As a disclaimer, while a variety of genres are present in this playlist, there are no tracks by Hip-Hop artists. While I enjoy some artists’ music from Chicago’s “Hipster Hop” scene, such as The Cool Kids, Chance the Rapper, and Kid Sister, they did not make my top 30.
Enough ado, here’s the playlist.
- “Chicago” (2011), Tom Waits from Bad as Me
It seems appropriate to begin with a song that depicts the plight of those who ended up in Chicago during the Great Migration. Waits’ lyrics present a biographical interpretation of the sentiments of many of the jazz and blues artists featured in this playlist:
To leave all we’ve ever known For a place we’ve never seen Maybe things will be better in Chicago.
- “You’re Gonna Miss Me (When I’m Dead & Gone)” (1948), Muddy Waters from The Essence of Muddy Waters
While originally from Mississippi, the former longtime resident of North Kenwood is widely considered the greatest and most influential artist in Chicago blues history. He was Chess Record’s first major breadwinner in the late 40s, pioneering and popularizing the hybrid of Delta and electric blues. Waters’ signature slide guitar is featured prominently on this early rock and rollesque tune. Runner Up: “Honey Bee” (1951) from The Essence of Muddy Waters
- “Come On! Feel the Illinoise!” (2005), Sufjan Stevens from Sufjan Stevens Invites You To: Come On! Feel the Illinoise!
This may be the ultimate ode to Chicago history and its prominent figures. Part 1 addresses the conflict between artistic and architectural integrity vs. consumerism in the 1893 World’s Columbian Exposition, where Cream of Wheat, soft drinks, and the Ferris Wheel were introduced. Stevens ponders whether Frank Lloyd Wright would approve of the spectacle (Louis Sullivan, his mentor and boss at the time, was adamantly opposed to the neoclassical buildings). The ghost of Carl Sandburg, most well known for his poem “Chicago” (the source of the moniker “City of the Big Shoulders”), appears to Stevens in a dream in Part 2. Again, artistic merit is the central theme as Sandburg’s ghost asks Stevens, “Are you writing from the heart?”
- “Heebie Jeebies” (1926), Louis Armstrong from The Best of the Hot 5 and Hot 7 Recordings
Armstrong arrived in Chicago from his hometown of New Orleans in 1922 at the age of 21 after receiving an invitation to join King Oliver’s Creole Jazz Band. While enjoying success as the trumpeter of Oliver’s band, Armstrong became the most famous jazz musician across the country as the bandleader of the Hot 5 and Hot 7. “Heebie Jeebies” catapulted him into stardom with the particular novelty of being one of the first recordings to feature scat singing. Armstrong was one of many famous Chicagoans who resided in Bronzeville during the era. Runner Up: “King of the Zulus” (1926) from The Best of the Hot 5 and Hot 7 Recordings
- “My Love Will Never Die” (1956), Otis Rush from The Essential Otis Rush
A left-handed guitarist, who played with an “upside-down tuning”, Rush’s sound was strongly identified with West Side blues. This song is one of several in this playlist written by Willie Dixon, Chicago’s most prolific blues songwriter. There’s a nice pairing of minor key blues with Rush’s pleading lines such as “Darling I know it’s my mind breaking out from the inside”.
- “We’re a Winner” (1967), The Impressions from We’re a Winner
This Curtis Mayfield penned hit was one of the first anthems of the Black Pride Movement. Performed in front of a small audience in a Chicago studio to give the recording a collective feel, the lyrics offer encouragement for advancement. Mayfield would of course revisit this theme in several songs, especially in his solo career. More on him later in the mix. Runner Up: “Seven Years” (1969) from The Young Mods’ Forgotten Story
- “Good Morning” (1936), Memphis Minnie from Memphis Minnie Vol 2 1935-1936
By the time Memphis Minnie arrived in Chicago, she had already seen and experienced the seedy street life of Memphis as a teenage runaway, street performer, and part-time prostitute. She had also traveled the South with the Ringling Brothers Circus and recorded some popular blues records in New York, such as “When the Levee Breaks”. In the 30s she became one of the most famous and respected artists of the Chicago blues scene. “Good Morning”, in which she confronts her husband’s infidelity, is representative of her mostly autobiographical compositions. Runner Up: “I Hate to See the Sun Go Down” (193?) from Hoodoo Lady (1933-1937)
- “Chicago at Night” (2001), Spoon from Girls Can Tell
The Austin based group, led by Brit Daniels, depict the arrival and downfall of a young woman who experiences the city at night for the first time. It’s dark, it’s been raining, and she wakes up with leaves in her mouth. We know something bad went down “because she knew that it was all over and we’d hit a wall”.
- “Spoonful” (1960), Howlin’ Wolf from The Chess Box: Howlin’ Wolf
Another famous blues tune written by Willie Dixon, “Spoonful” is basically about some common vices and the lengths we go for them. Wolf was another Mississippi transplant that became a star while recording with Chess. The influence of his signature growl and one-chord song construction can be heard in a wide range of musicians, perhaps most recognizably in the work of Tom Waits (see track#1). Runner Up: “Smokestack Lightning” (1956) from The Definite Collection
- “Dark Side” (1966), The Shadows of Knight from Gloria
The garage rock of The Shadows of Knight was a mix of the British invasion sound with Chicago blues. Originally from Mt. Prospect, the group gained moderate radio success with their cover of Them’s “Gloria”. With a strong Stones’ influence, “Dark Side” was one of the group’s best original compositions. Runner Up: “Light Bulb Blues” (1966) from Gloria
- “Stack-O-Lee” (1958), Champion Jack Dupree from Blues from the Gutter
Dupree, who became an orphan before turning 3, was born and raised in New Orleans, where he learned to play piano and perform. After a stint as a successful boxer in Detroit, where he got his name “Champion Jack”, he established himself in the Chicago blues scene. “Stack-O-Lee” is a traditional song that tells the true events of a St. Louis pimp, Stagger Lee, who took William Lyons’ money, Stetson hat, and then his life.
- “Far, Far Away” (1996), Wilco from Being There
Though many of the songs on Being There were a departure from Jeff Tweedy’s alt-country material in Uncle Tupelo, “Far, Far Away” is one of the Wilco’s most straightforward country ballads. Tweedy sings about missing his wife, who is under Chicago’s city lights while he is on tour on the other side of the country (on the other side of the moon). He then fantasizes about kissing her on the CTA. This track features some great pedal steel work by Chicagoan Bob Egan (Freakwater, The Sadies, Neko Case). Runner Up: “Handshake Drugs” (2004) from A Ghost Is Born
- “King Porter Stomp, No.1” (1923), Jelly Roll Morton from The Library of Congress-Jelly Roll Morton
The descendent of a long line of Black French Creoles in New Orleans, Morton is considered to be one of the most significant early jazz pioneers. A constant self-promoter, he claimed that he singlehandedly invented jazz. While living in Chicago in the 20s, Morton and his band, The Red Hot Peppers, recorded some early jazz classics, including Morton’s own “King Porter Stomp”. He claimed to have written the tune many years before as a teen while he was a regular performer in brothels. Runner Up: “Wolverine Blues” from Birth of the Hot – the Classic Chicago “Red Hot Peppers” Sessions 1926-1927
- “You Can’t Judge a Book By Its Cover” (1962), Bo Diddley from Bo Diddley: The Chess Box
Bo Diddley moved from Mississippi to the South Side with his family when he was 6. His first instruments were the trumpet and violin, which he picked up at Ebenezer Baptist Church in the Oakland neighborhood. Eventually, his interest drifted to the guitar and Chicago blues. Over time Diddley’s style would incorporate R&B, rock and roll, and rockabilly. Considered one of the godfather’s of rock and roll, his influence can be heard in 60s albums by The Rolling Stones, The Velvet Underground, and The Beatles. “You Can’t Judge a Book By Its Cover” was another Willie Dixon composition. Runner Up: “Ride On Josephine” (1960) from Bo Diddley: The Chess Box
- “Oh No” (2009), Andrew Bird from Noble Beast
The Lake Forest native spent many years living in Chicago neighborhoods, including Edgewater and Logan Square while maintaining a farm retreat in Western Illinois. From studying classical violin at Northwestern to indie folk star, his sound has dramatically evolved over his career. Bird gave insight into the inspiration and meaning behind “Oh No” when he wrote a songwriting feature for a New York Times blog project. He revealed that while taking a flight from New York to Chicago, he sat near a deeply afraid and tearful toddler, who slowly repeated the words “Oh no” to himself. The young boy’s sense of desperation and his childhood memories of exploring the ravines in Lake Bluff inspired Bird to write this escape fantasy. Runner Up: “Plasticities” (2007) from Armchair Apocrypha
- “Saturn” (1959), Sun Ra from Jazz in Silhouette
The scope of Sun Ra’s eccentricity is a challenge to get across in a small blurb. Along with George Clinton’s Parliament and Funkadelic, his music and persona were commonly associated with Afrofuturism, the artistic movement combining science fiction with Afrocentrism. While in college in his home state of Alabama, Sun Ra claimed he had a cosmic vision in which he discovered that he was actually from Saturn. He was a conscientious objector after being drafted in 1942. Shortly after finally being discharged, he came to Chicago in 1945. The city brought him into contact with many black intellectuals and political movements and also inspired him with its many Egpytianesque buildings. In 1952, still during his Chicago years, he anointed himself Sun Ra (after the Egyptian Sun God). Though “Saturn” is a tribute to the pianist and bandleader’s cosmic home, the track and album Jazz in Silhouette are quite accessible. He left Chicago for New York in 1961, and soon thereafter began his more “out there” experimental free-jazz period. Runner Up: “Soft Talk” (1956) from Supersonic Jazz
- “Black, Brown, and White” (1949), Big Bill Broonzy from Big Bill Broonzy: Absolutely the Best
When “Black, Brown, and White” was released, it was revered by the white folk artists and enthusiasts (like pal Studs Terkel) who preferred a more “authentic” stripped down acoustic sound. Even with its anti-racism theme, some in the blues community did not appreciate this sonic departure. Up until this point, Broonzy had been a staple of the Chicago blues scene, often sharing the bill with Memphis Minnie in Chicago clubs. He also wrote and recorded continuously over his long career in the city. He simultaneously held a series of side jobs and positions, ranging from Pullman porter in the 20s to one of the founding members of the Old Town School of Folk Music in 1957. Runner Up: “Good Liquor Gonna Carry Me Down” (1935) from The Young Big Bill Broonzy
- “Four Corners” (2003), The Sea and Cake from One Bedroom
The Sea and Cake seems to be the ultimate band for artists. Lead singer Sam Prekop and guitarist Archer Prewitt, who is also a professional cartoonist, met in art school. Bass player Eric Claridge is a painter and illustrator and drummer John McEntire, also of the Chicago post rock group Tortosie, studied percussion and Music technology at Oberlin Conservatory. Prekop, whose father taught at the Art Institute and mother was a clothing designer, was raised in Bucktown and Hermosa. The dreamy synth heavy “Four Corners” with McEntire’s backbeat is an impressive opening track on the solid One Bedroom. Runner Up: “Sound and Vision” (2003) from One Bedroom (Cover of David Bowie’s 1977 tune)
- “Eisenhower Blues” (1954), J.B. Lenoir from Chess Blues Classics 1947-1956
After arriving in 1949, Lenoir settled into the Chicago blues scene with the help of his mentor Big Bill Broonzy. Many of his songs had a political edge that was deemed too controversial to be released by various record companies. Initially, he was forced to rerecord “Eisenhower Blues” as “Tax Paying Blues” by the Parrot label. When put into context of the early 50s, “Eisenhower Blues” is remarkable in that a black blues artist is openly critiquing the president’s disregard for the working class.
- “Hitch Hike” (1966), The Sonics from Boom
Originally written and recorded by Marvin Gaye in 1962, “Hitch Hike” details the travel itinerary of a broke man searching for his rolling stone girlfriend. He makes it to Chicago where she was last known to be, but we don’t find out if he has any luck. The Sonics’ raw garage rock rendition provides a nice bit of edge. Runner Up: “Hitch Hike” (1962), Marvin Gaye from Gold: Marvin Gaye
- “Hit the Ground Running” (1999), Smog from Knock Knock
Knock Knock was the first of several albums that Bill Callahan (Smog) released in his 5 years living in Chicago. It was produced and engineered by Chicagoan Jim O’Rourke (Sonic Youth, Loose Fur). Multiple tracks feature the Chicago Children’s Choir, including the nearly 7-minute “Hit the Ground Running”. The Children’s Choir is the perfect complement to Callahan’s baritone and wit. Runners Up: “Our Anniversary” and “Truth Serum” (2003) from Supper
- “Dipper Mouth Blues (Version 1)” (1923), King Oliver’s Creole Jazz Band from Ultimate Collection
Joe “King” Oliver came to Chicago in 1918 to escape the restrictive Jim Crow south. Despite the social climate, he had enjoyed quite a bit of success as a performer in New Orleans and mentored a young a Louis Armstrong. Once Oliver became well-established in Chicago, he brought Armstrong to the city to join his band. You can hear Armstrong in this recording, but King Oliver’s cornet solos are the highlight. This recording is considered an early jazz classic.
- “A Change is Gonna Come” (1964), Sam Cooke from Portrait of a Legend 1951-1964
Sam Cooke’s family moved from Mississippi to Chicago in 1933 when he was 2. He grew up in Bronzeville, where he, as well as Nat King Cole, attended Wendell Philips Academy High School. He became a major star with hits like “You Send Me” and “Another Saturday Night”, but “A Change is Gonna Come” may the song for which he has received his most artistic praise. It became one of the prominent anthems of the Civil Rights Movement as the lyrics addressed discrimination Cooke faced as a performer traveling through the South and the need for societal change. In 2011, a portion of 36th street, near Cottage Grove, was designated “Sam Cooke Way”.
24. “Shake That Thing” (1925), Papa Charlie Jackson from Too Late, Too Late Vol. 11 (1924-1939)
Not much is known about Papa Charlie Jackson other than he was originally from New Orleans and most of his career as a musician took place in Chicago. He was apparently a staple of the Chicago club scene and street performer at the Maxwell Street Market. This recording features Jackson on the banjo guitar with his blend of blues and ragtime.
- “21 Days in Jail” (1958) from The Essential Magic Sam: The Cobra and Chief Recordings 1957-1961
Along with Otis Rush and Buddy Guy, Magic Sam was a star of the West Side blues scene. At the age of 19, he signed with the west side independent label Cobra where this track was recorded and produced. This up-tempo rockabilly tune about a terrifying experience of serving time was co-written by Willie Dixon, who is also featured on bass in the recording. Magic Sam was just on the verge of gaining international fame when he abruptly died of a heart attack at 32 in 1969. His influence can be heard in the succeeding generation of blues musicians who emulated his style.
- “Chinese Apple” (2003), Loose Fur from Loose Fur
While working on the initial recording for Wilco’s groundbreaking Yankee Hotel Foxtrot, Jeff Tweedy enlisted Chicago musician and recording engineer Jim O’Rourke to collaborate on a side project that became Loose Fur. For the recording, O’Rourke brought in Glenn Kotche on drums. The trio’s collaboration ended up greatly influencing the final version of Yankee Hotel Foxtrot as Tweedy asked O’Rourke to replace Jay Bennett as engineer and Kotche to take over for Ken Coomer on drums. At almost 8 minutes, “Chinese Apple” shares some lyrics with Wilco’s “Heavy Metal Drummer” and includes a noise break reminiscent of other tracks on Yankee Hotel Foxtrot.
- “Snatch It Back and Hold It” (1965), Junior Wells’ Chicago Blues Band from Hoodoo Man Blues
After leaving Memphis for Chicago in 1948, Wells quickly made a name for himself as a harmonica player and bandleader. For his album Hoodoo Man Blues, he assembled a group of local blues players that included his frequent collaborator Buddy Guy on guitar. Wells and Guy would go on to stardom, playing with such icons as The Rolling Stones and Van Morrison. “Snatch It Back and Hold It”, like other songs on the record, captures the ambience of the 60s Chicago blues club scene. Runner Up: “I Could Cry” (1957) from Calling All Blues
- “Little Child Running Wild” (1972), Curtis Mayfield from Superfly
Born in Chicago in 1942, Mayfield spent most of his youth growing up in various housing projects, including his teenage years in Cabrini-Green. He dropped out of Wells High School in West Town to pursue music full-time, eventually becoming lead singer and primary songwriter for The Impressions. The Mayfield compositions “Keep on Pushing” and “People Get Ready” were instant anthems of the Civil Rights Movement. As a solo artist, he penned some of the most famous Black Pride and social commentary tunes of the 70s like “Move On Up” and “Pusherman”. Often considered his masterpiece, his soundtrack album Superfly examined the despair of the urban ghetto. “Little Child Running Wild”, originally titled “Ghetto Child”, is a reflection on Mayfield’s observations of neglected youth growing up in the projects. Runner Up: “Move On Up” (1970) from Curtis
- “Got the Bottle Up and Gone” (1937), Sonny Boy Williamson from Sonny Boy Williamson Vol. 1 (1937-1938)
Sonny Boy Williamson came to Chicago from Tennessee in 1934. He is recognized as one of the early pioneers of the blues harmonica. Williamson enjoyed a great deal of success in the Chicago blues scene until he was murdered during a robbery near his Bronzeville home in 1948. The country blues recording “Got the Bottle Up and Gone” displays Williamson’s harmonica prowess.
- “Chicago” (2005), Sujfan Stevens from Sufjan Stevens Invites You To: Come On! Feel the Illinoise!
It’s seems fitting to begin and end the playlist with a track simply titled “Chicago”. Stevens earns a second spot on the playlist since he dedicated an entire album to Illinois. This is perhaps the most autobiographical song of the album, as the Michigan native acknowledged in several interviews that his visits to Chicago as a young man had quite an impact on him. In “Chicago”, he explores the lure and romanticism of the exotic big city.
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