10. Steve Goodman – “A Dying Cubs Fan’s Last Request”
Like the Cubs’ century without a World Series title isn’t depressing enough, Goodman’s tale of a fan who spent a long life root- root- rooting for the “doormat of the National League” might bring a tear to your eye—until you guffaw at some of his last words: “I’ve got season’s tickets to watch the Angels now…but you, the living, you’re stuck here with the Cubs/So it’s me who feels sorry for you.”
09. Rhett Miller – “The El”
It wouldn’t be a Chicago playlist without a song about “rattling along on the El,” that institution of Chicago mass transit. This catchy pop tune is from the Old 97′s frontman’s solo debut The Instigator
08. Paper Lace – “The Night Chicago Died”
If this song isn’t on your iPod, it’s on your list of go-to karaoke songs. Whether you sing the actual chorus recorded by these two-hit wonders or the version Jack Black sang in High Fidelity is up to you. Gloooooory be!
07. Sufjan Stevens – “Come On! Feel the Illinoise!“
We’d be remiss if we didn’t include a song from Stevens’ 2005 tour de force Illinois. This nearly seven minute opus has two parts: the first about the World’s Columbian Exposition in 1893 and its myriad attractions (the world’s first Ferris Wheel, the White City are two that feature prominently in Stevens’ lyrics), the second about author/poet Carl Sandburg, who, of course, wrote the poem “Chicago.”
06. Kanye West feat. Chris Martin – “Homecoming“
West—joined by piano and vocals from Coldplay’s Chris Martin—raps a love letter to his hometown, which he imagines as a girl named “Wendy” in a clever take on Chicago’s “Windy City” moniker.
05. Graham Nash – “Chicago“
Nash scored a Top 40 hit in ’71 with this song, which was inspired by the riots in Chicago during the 1968 Democratic National Convention and subsequent trial of the Chicago Eight.
04. Bessie Smith – “Chicago Bound Blues“
Several have recorded this song, but nobody sounds quite like Bessie when she wails “Blues on my brain/My tongue refused to talk.” Luckily said tongue was okay with singing—they don’t call her “Empress of the Blues” for nothing.
03. Elvis Presley – “In the Ghetto“
This depressing tale of urban poverty and violence, released in 1969, was Elvis’ first U.S. Top 10 hit in four years. Since then it’s been recorded by Dolly Parton, Nick Cave, and several other artists.
02. Frank Sinatra – “Chicago“
Fred Fisher penned this tune about the toddlin’ town that evangelist and Prohibition advocate Billy Sunday could not shut down. Too bad Ol’ Blue Eyes is no longer around for us to take him up on his offer to “show [us] around.” That sounds like the definition of a good time.
01. Robert Johnson – “Sweet Home Chicago“
I have no idea if the Delta Blues legend actually visited Chicago before his death at age 27. But this recording is one of the most important songs in the last century of American music.
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