Chicago. The very name helps form a half dozen compound nouns of American music. There’s Chicago-Blues, Chicago-Jazz, Chicago-Rap, Chicago-Rock. As the cultural center of the Midwest, Chicago is the epicenter of the clashes and collaborations between North and South, East and West. This shared history between the different regions comes out in its music. On your next trip to Chicago, take the time to explore the diversity and depth of the Windy City’s music. Whether it’s hip-hop, gospel, jazz or rock, Chicago’s contributed to the best of each genre. This playlist pays tribute to the great musical heritage of the White City.


1. Be (Intro) – Common – 2005

Produced by Kanye West and following the commercial disaster that was his previous album Electric Circus, Common’s album Be, cemented his place in the pantheons of avant-garde rap. If rap has a public image (not without reason) of violence, drugs and misogyny, Common helped dispel the trend with albums that combine elements of soul, gospel, and jazz to create smooth sonic experiences filled with messages of empowerment and self-improvement.

With Be, Common found the producer he’d always needed in West, and the result was one of the best albums of 2005. To begin this playlist, we’ve gone with the album’s first track. From the opening bass line to the layering of voices, everything that showcases the best of Common’s soulful style and West’s production genius are on display here.

2. 1979 – The Smashing Pumpkins – 1996

Alt-rock in the 90’s was still the derivative younger brother of Grunge Rock and the remnants of the 80’s. Crunchy power chords, simplistic riffs and drumlines had come to define the genre. That would all change with The Smashing Pumpkins.

1979, taken from their third album Mellon Collie and the Infinite Sadness, added a rich symphonic atmosphere, and lyrics that covered an emotional range unseen in alt-rock. In the process, The Smashing Pumpkins became one of the 90’s most popular bands, as well as one of Chicago’s most beloved exports.

3. Here It Goes Again – OK Go – 2006

The mid 2000’s were a golden age for pop-rock and few exemplify the era like OK Go. Their jumpy guitar work, energetic lyrics and bizarre music videos helped make them one of the decade’s most popular pop-rock acts as well as defining the future for hundreds of other bands. Here It Goes Again was one of 2006’s most popular singles as well as one of the original YouTube viral music videos.

4. We Don’t Care – Kanye West – 2004

There is perhaps no musical artist more polarizing than Kanye West. Even Kanye West fans find it hard to defend his actions, and that’s before his political meltdown, MAGA hat wearing Trump hug, SNL outburst, and subsequent turn to gospel rap.

But whatever his personal antics, his influence in music is undeniable. Just a year before his revolutionary album The College Dropout dropped, rap was an industry dominated by gangster imagery, mass produced beats and tired, simple rhythms. In 2003 the largest stars in hip-hop were 50 Cent, Ja Rule and Nelly. Within a year after The College Dropout they were all swept aside for a new generation of melodically styled rappers.

Kanye West’s injection of socially conscious lyrics, musical sampling from a wide variety of genres, and collaborative energy ushered in related artists such as Frank Ocean, Kid Cudi, and Chance the Rapper. On the track We Don’t Care, we hear all the elements that made The College Dropout so ground-breaking.

5. What Kind of Woman Is This? – Buddy Guy – 2005

In the world of Chicago Blues, one name reigns supreme, Buddy Guy. While born and raised in Louisiana, it would be in Chicago where Guy would get his start and later add his name to the pantheon of Blues stars. Commonly referred to as the world’s greatest living guitarist, Buddy Guy’s career spans decades of musical accomplishments.

6. Move On Up – Curtis Mayfield – 1970

There are few bigger names in Soul music than Curtis Mayfield. The influential guitarist, singer-songwriter as well as political activist was behind some of the biggest soul hits of the70’s. Move On Up is a perfect example of his unique blend of R&B and socially conscious songwriting.

7. Free Soul – Mykele Deville – 2019

This rising rapper is a star of Chicago’s indie DIY rap scene and a staple at underground shows in the city. Deville originally was drawn to fiction and wanted to write short stories and novels. But he ended up finding his voice through music rather than prose. Free Soul showcases Deville’s biting commentary on modern social ills.

8. Giant of Illinois – Andrew Bird – 2014

An enduring name in the ocean that is indie folk, Andrew Bird’s unique musicality and poignant writing has powered a prolific career. Giant of Illinois references the state and city that Bird calls home and explains his lasting popularity.

9. Savior – Rise Against – 2008

Few bands can combine catchy hooks, frenetic energy and wide-ranging social commentary like Rise Against. Rise Against was one of the most popular punk bands of the 2000’s to come out of Chicago and were critically acclaimed for their lyrical impact.

10. Kind of Love – Tasha – 2018

Singer, songwriter, poet, activist, Tasha is used to wearing a lot of hats. On her debut album, she makes use of music to tell her story as a young queer woman navigating the social landscape of modern America. Kind of Love shows the emotional depth Tasha brings in her music.

11. Old School Love – Lupe Fiasco (Feat Ed Sheeran) – 2013

Often overshadowed by the city’s more commercially successful rappers, Lupe Fiasco is still one of Chicago’s favorite sons. One of the original pioneers of the 2000’s social-conscious rap, Lupe Fiasco often wrote about the effects of poverty, gun violence and drug abuse. While Old School Love is one of his more peaceful tracks, the specter of “Chiraq” still looms present in all his work.

12. Prom Queen – Beach Bunny – 2018

Beach Bunny was originally a fun side project for Lili Trifilio to cope with the stress of college. But her band would eventually rise to popularity in the indie DIY movement of the late 2010’s and even sign with Mom+Pop Music in 2019.

13. Sugar, We’re Going Down – Fall Out Boy – 2005

Hailing from Wilmette, just outside Chicago, Fall Out Boy might be one of the Second City’s most popular rock exports. Out of all the glorious destruction that was emo-rock in the 2000’s no band was more universally hated or successful as Fall Out Boy. While critics often derided their music as watered down, derivative and generic, a reviewer in 2009 conceded that “Sugar, We’re Going Down” was probably the “most listened-to emo track of all time” And while they’ve morphed and adapted with the musical times, Sugar, We’re Going Down is a throwback to their early pop-punk days.

14. Renegade – Styx – 1978

Styx was one of the most popular bands of the late 70’s and one of the first alternative bands to make the transition to progressive rock. Renegade is one of their most popular singles and became an iconic song of the prog rock genre.

15. Give It Away – The Chi-Lites – 1969

One of the most popular R&B/Soul groups of the 1970’s, the Chi-Lites were a quartet based out of Chicago. While their star only burned bright for a few years, their influences are still heard in R&B today, and in 2013 they were inducted into the Rhythm and Blues Hall of Fame.

16. Never Said – Liz Phair – 1993

While her career took a decidedly more pop turn with her album Liz Phair in 2003, Liz Phair was one of original female alt-rock acts of the 90’s. In her track Never Said, this casual cool and subtle rebellion exudes through her languid vocals and raspy chords.

17. September – Earth, Wind & Fire – 1978

Call it disco. Call it funk. Call it soul. But whatever you call it, Earth, Wind & Fire had it. September was released in 1978 and went #1 on the US R&B charts and certified Gold, while also landing themselves on every wedding dance soundtrack ever.

18. A Change is Gonna Come – Sam Cooke – 1964

Entrepreneur, civil-rights activist and of course, the King of Soul, Sam Cooke was a fixture of the Chicago Soul Music scene for years. His popularity, influence and talent helped foster the next generation of soul singers of Aretha Franklin, Stevie Wonder and Marvin Gaye. In A Change is Gonna Come, Cooke’s talent and distinctive vocals are stunningly obvious.

19. 65th & Ingleside – Chance The Rapper – 2018

Chicago has made many hip-hop stars, but few have been as dedicated to giving back to their community as Chance the Rapper. Whether it’s his involvement with community engagement or hanging out with the Obama’s; Chance the Rapper is as much a fixture of the Windy City as the Willis Tower. In 65th & Ingleside, he reminisces on a past life spent in his youth in the city that would indelibly be associated with his music.

20. Cantaloupe Island – Herbie Hancock & Co – 1964

In the world of American Jazz, a few cities stand out. New Orleans, New York City, and Chicago. Chicago came to be known for forming its own unique blend of jazz, and few proponents of it achieved as much fame as Herbie Hancock. The pianist, and later band leader, composer and even actor, would become one of the most influential jazz pianists of his generation. In Cantaloupe Island he delivers a composition that would go on to become a jazz standard.


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