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20. Lupe Fiasco: Food & Liquor (2006) Fiasco’s hyperliterate rush of words touches on everything from Islam to skateboards and demonstrates hip-hop’s infinite potential.
19. Ministry: The Land of Rape and Honey (1988) Creepy vocals, grinding guitars, jackhammer beats: This is the one that paved the way for a zillion industrial metal bands, for better or worse.
18. R. Kelly: 12 Play (1993) This smash made Kelly a legend in the R & B world with soulful songs that detailed the Roseland native’s sexual prowess—and became vaguely creepy in retrospect.
17. Chicago Transit Authority: Chicago Transit Authority (1969) Spanning progressive rock and jazz fusion before either sank into self-indulgence, this ambitious double album stayed on the charts for three years.
16. Big Black: Atomizer (1986) Steve Albini’s masterpiece is snide, brutal, and intelligent—i.e. everything to which eighties post-hardcore aspired.
15. Earth, Wind & Fire: That’s the Way of the World (1975) A danceable hybrid of soul, funk, Latin, and disco that went triple platinum and produced what Rolling Stone called “makeout music of the gods.”
14. Cheap Trick: Cheap Trick (1977) Too polished for the punks and too raw for the radio, this goofy, hooky debut documents a band untethered, before they knew how good they were.
13. Herbie Hancock: Maiden Voyage (1965) Essential to any jazz collection, this was the modal jazz groundbreaker that showed Hancock—an alum of Hyde Park High—wasn’t just Miles Davis’s pianist.
12. Tortoise: Millions Now Living Will Never Die (1996) Smarter than a Mensa meeting and odder than a Lynch film, this unlikely brew of jazz, dub, krautrock, and chamber music generates a wistfully weird mood.
11. John Prine: John Prine (1971) Critics crowned the 24-year-old former Maywood mailman “the next Bob Dylan” for this brilliantly written country/folk debut. He almost was.
10. Kanye West: The College Dropout (2004) Wherein the Oak Lawn kid fulfilled his tremendous promise with intelligent, tongue-twisting rhymes and versatile MC skills.
9. Andrew Bird: The Mysterious Production of Eggs (2005) Bird’s mellow, atmospheric tour de force gleefully thumbs its nose at any genre labels—and mesmerizes for 53 minutes.
8. Louis Armstrong: The Complete Hot Five and Hot Seven Recordings (2000) If you want to know where jazz came from, this treasure-trove of recordings from 1925 to 1929 (when Chicago was the jazz epicenter) is a good place to start.
7. Liz Phair: Exile in Guyville (1993) Equal parts cryptic and desperately blunt, this New Trier grad’s lo-fi indie classic pulses with a deadpan humor and anger that few have ever matched on record.
6. Curtis Mayfield: Superfly (1972) Mayfield’s funky grooves and gritty stories—reflecting his upbringing in the Cabrini-Green projects—captured the sound of inner-city streets without moralizing or glorifying.
5. Muddy Waters: The Chess Box (1989) This 72-song boxed set spanning 25 years is the only way to do justice to the man who, in all his swampy slide-guitar glory, basically invented Chicago blues.
4. Naked Raygun: All Rise (1986) Spawning imitators around town, this artsy, hardcore album throbs with old-school, muscular punk rock—and brains to boot.
3. Smashing Pumpkins: Siamese Dream (1993) Billy Corgan’s attempt to one-up Nirvana resulted in one of the decade’s definitive discs: heavy, dreamy, and layered in sonic noise, it nearly succeeded.
2. Willie Dixon: The Chess Box (1988) The definitive Chicago blues compilation: 36 Dixon-penned classics played by Chess Records’ legendary performers, including Dixon—the best blues songwriter ever.
1. Wilco: Yankee Hotel Foxtrot (2002) Wilco overcame drug problems, infighting, and record-label drama to create an unforgettable album that will define Chicago for generations of music fans. A lush, chaotic record that only gets better with time (and repeated spins), YHF’s weary forays into psychedelia and noise inadvertently caught the post-9/11 anguish better than any other album.
Photography: (exile in guyville) matador records, (wilco) chris strong, (naked raygun) quarterstick records, (millions now living will never die) thrill jockey records
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