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Updated by DJ Rob on Oct 22, 2016
Headline for Best 25 Musical Artists from Chicago - Ever!
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Best 25 Musical Artists from Chicago - Ever!

With the Chicago Cubs advancing to the World Series for the first time since 1945, djrobblog pays tribute to the Windy City with a countdown of the 25 greatest musicians to hail from the nation's third largest city.

Any true Chicagoan knows that not everyone in the city is celebrating the Cubs' first National League Pennant in 71 years, as those on the city's south side - being true fans of cross-town rivals the White Sox - likely took the first red line train out of the Loop when the Cubs turned the game's final double play to seal their trip to Cleveland.

But regardless of which Chicago team one roots for, or which side of the city Chicagoans claim as their own, all Chicagoland residents can be proud of the rich musical legacy that the city's artists have created over the decades.

So it is with that and the Cubs' victory in mind that I've updated this special djroblist of the best musicians to have ever called Chicago or its suburbs home.

Here it is from #25 to #1 in countdown fashion.




Tied - 25. Paul Butterfield

Tied - 25. Paul Butterfield

Notable songs: "I Got My Mojo Working" (1965); "Born In Chicago" (1965); "Shake Your Money Maker" (1965).

Paul Butterfield was born in Chicago in 1942. He was raised in the Hyde Park area and played with great Chicago Blues artists like Muddy Waters (who comes up later on this list), Howlin' Wolf and others. Unlike most of the rock and roll greats coming out of the Chicago Blues scene, Butterfield's specialty was the harmonica, which is featured prominently on his band's songs. Butterfield died in 1987 at a young age and his group, The Paul Butterfield Blues Band, was inducted in the Rock and Roll Hall of Fame in 2015.

  • DJ Rob


    Hi, I'm DJ Rob, owner and author of the music blogsite I live in Chicago, IL and have been doing the blogsite since January 2015. It features articles about music news, history and trivia - both old and new. The features I enjoy doing the most are my djroblists. I've done dozens of lists ranking everything from blue-eyed soul singers to Prince's greatest songs. I only recently started converting them to listly to increase interaction with my readers. Take some time to enjoy them and let me know what you think! And check out when you can!

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