Chicago has the best or second best in America of basically everything, but it has historically lacked an intriguing music scene. Where Detroit has Motown and techno, San Francisco has psychedelic rock and folk, Seattle has grunge and indie rock, Austin has folk, Nashville has country, and New York has punk, post-punk, new wave, hip-hop, etc., Chicago doesn't really have a well-known genre at its core.
To Chicagoans though, Chicago does have a rich musical history. From Chess Records and blues and jazz to House music to Touch and Go, Thrill Jockey, and the experimental rock of the '80s and '90s, Chicago has always had good music. Venues like the Metro, the Aragon, the Riviera, the Double Door, and the Chicago Theatre have housed some pivotal music moments. But to outsiders, Chicago's music scene seems confusing and mostly nonexistent.
Despite not necessarily having a particular scene or movement associated with it, Chicago has been home to many amazing--albeit singular--bands. These are my favorites, the ones that make me proud to live here. (Bands are judged both on quality of music and Chicago-ness.)
1. Big Black/Rapeman/Shellac/Steve Albini
The common thread here is Steve Albini. Albini, with these three bands, created the finest noise-rock of the '80s and '90s. He perfected the sound--a riff on punk and post-punk--that helped give birth to noise-rock as we know it and industrial. Since the early '90s, he's been producing great albums as well (Jesus Lizard, Nirvana, Breeders) from his Chicago studio, Electrical Audio. He is modern Chicago rock music more than anyone.
2. Buddy Guy
Buddy Guy, like many of the "Chicago" bluesmen, was not born in Chicago, but in the south. However, since coming to Chicago, he has been instrumental in the foundation and progression of electric blues. He opened a blues club, Buddy Guy's Legends, in Chicago to help preserve the legacy of Chicago blues. As Albini is Chicago rock music, Guy is Chicago blues. He was born in Louisiana, but he is quintessentially Chicago.
3. Curtis Mayfield
Both with the Impressions and on his own, Curtis Mayfield made some of funkiest soul music in the world, let alone Chicago. And, unlike the previous two on the list, the man was actually born and raised in the city, which certainly gives him a high level of Chicago-ness. Super Fly remains his highest achievement, but being born in Chicago is a close second.
4. The Jesus Lizard
The Jesus Lizard (who were produced by Steve Albini) coupled heavy, aggressive, noisy, and amazing grunge songs with one of the wildest live shows around. Though I didn't see them until their reunion this year (and not in their early '90s heyday), it was evident that these guys are still very great and still very Chicago (as evidenced by David Yow's Hot Doug's T-shirt).
Tortoise is another member of the group of Chicago experimental rockers from the '90s, and they are Chicago record label Thrill Jockey's premier artist. The music--jazz, prog, and minimalist classical influenced post-rock--is some of the finest to ever come from this fair city, and the band continues to show their love of Chicago by performing here a lot.
6. Art Ensemble of Chicago/Roscoe Mitchell
The Art Ensemble of Chicago gains points for Roscoe Mitchell being born in Chicago, and they gain a ton of points for having Chicago in the name. Like another band with Chicago in the name (Chicago), they play jazz, but unlike that other band, they're great. They delve deep into the avant-garde, wear tribal costumes, and play like few other jazz collectives can.
Another rock band unafraid to experiment that hails from Chicago is Ministry. Frontman Al Jourgenson was born in Cuba, but raised in Chicago, which makes him an honorary Chicagoan, and the bulk of Ministry's work has come out of the city. Ministry is certainly one of the most important and best industrial groups and most important and best Chicago groups.
8. Smashing Pumpkins
To the outside world of music fans and critics and stuff, Smashing Pumpkins are Chicago's music scene. They are indeed the most famous of the grunge-y Chicago bands of that era, and Corgan, Iha, and Chamberlain are all Chicago (or Chicago suburbs) born and bred. The reality is, they probably are the most important Chicago rock band, whether I like it or not.
9. Frankie Knuckles
Frankie Knuckles essentially invented house music. Here in Chicago, there's an honorary Frankie Knuckles Blvd. near the location of the Warehouse Club. That club is where Frankie took up a DJ residency and lay the foundation for house music. If there is one true genre associated with Chicago, it's house, and if there's one man associated with house, it's Knuckles.
10. R. Kelly
Though his musical output may not be as strong (but it's still pretty solid) as some others on this list, R. Kelly is one of Chicago's most famous, most beloved, and weirdest artists. His unique brand of spoken-word/sung R&B is good music and, sometimes, great comedy. Nonetheless, he is a Chicago artist through and through. (And I met him. One of the perks of living here: you could meet R. Kelly.)
And roundin' out the top 20...
11. Ken Vandermark
13. The Staple Singers
14. Red Red Meat
15. The Dells
16. Naked Raygun
17. The Shadows of Knight
18. Paul Butterfield
19. Rotary Connection
20. The Sea and Cake
That's what I think. Feel free to comment (if you're from here).