Cover Story: The 25 Greatest Chicago Songs

Illinois Entertainer presents:
The 25 Songs That Make Chicago Shake

With the album declining due to the Internet, we’re here to help kick it out the door and celebrate the songs that gave them life. But not just any songs: Chicago songs. Good grief, was this difficult. First, don’t ask what the parameters were – ink and paper are too expensive these days. Time’s continued crawl only raised the probability we’d snub a classic, so we kinda took a different tack. The highlighted songs are those our staff deemed indispensible to the city, its cultural history, and for that reason we’ve included a couple words explaining how each selection achieved such exalted status.

But to give it flavor (and cover our butts) we’ve surrounded the 25 with lists. People (and publishers) love lists, and we hope these help add context to the lustrous story of Chicago pop music, via doo-wop, garage rock, bare-knuckle punk, an embattled hip-hop scene, and, it took some digging to find enough examples, the blues.

Lastly, building this inspired a sense of civic pride (with a little help from Rockford). Peering an eye toward globalization, the World Wide Web, and nationalized (homogenized) radio, it’s getting harder to remember that music used to have intense regional rivalries. It’s in solidarity with our brothers packing an icy Wrigley Field on New Year’s Day that we ask you to join us as we sing: “Detroit sucks!”

Click here to begin, and here to see our companion lists.

– Steve Forstneger

Category: Features, Monthly