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

(This article was republished on October 23, 2016.  A previous version was published in May 2015.)

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 to meet the Indians in the Fall Classic.

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.

Chicago has long been known for its contributions in blues and blues-oriented rock music. Several of the genre’s biggest names – many of whom are Rock and Roll Hall of Famers – have hailed from this great city.

There are many non-RRHOF artists on this list as well – noteworthy ones who may be there soon, but whose musical accomplishments stand out nonetheless.

So I’ve come up with this ranking of who I consider to be Chicago’s 25 best, with a short story for each.  With lots of chart facts and figures and other information at my disposal, I think I’ve been able to come up with a list that – at the very least – approximates Chicago’s most influential, most successful acts of the rock-and-roll and hip-hop eras (i.e., from the 1950s to now).

I considered as eligible any solo artist who was born or raised in Chicago or any of the city’s many suburbs, or any band whose members were primarily born/raised in the area or which was formed here.  It also includes any artists who’ve spent a considerable amount of their lives here and have called it home.  Of course, these rankings also take into account record sales, chart performance, critical recognition, innovation, amount of influence and general popularity (and in some cases, level of disdain – which ironically can also be a measure of one’s significance in the industry).

So now I present to you this countdown of Chicago’s Best 25 Music artists.   You may disagree with the exclusion, inclusion or ranking of some of these musicians, and I welcome your views in the comment section below the article.

To hear the notable songs listed for each recording artist, click here for my Top 25 Chicago Artists playlist on Spotify.

Here they are:

Headline for Best 25 Musical Artists from Chicago - Ever!
DJ Rob DJ Rob
26 items   3 followers   0 votes   2.65k views

Tied - 25. Paul Butterfield

Oct 22, 2016
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.

Other notable Chicago-based musicians not making the list: The Emotions, Jennifer Hudson, Ministry, Ramsey Lewis, Gene Chandler, Flamingos, Donny Hathaway, Da Brat, Liz Phair, Lupe Fiasco, Veruca Salt, Disturbed, Warren Zevon, Benny Goodman, Jeremih, Phil Everly*, Herbie Hancock, Philip Bailey, Krewella, Plain White T’s, the Buckinghams, OK Go, Twista, Avant, Peter Cetera, Frankie Knuckles, Donell Jones, Impressions**

*Note – Phil Everly of the Everly Brothers was born in Chicago, but his brother Don was not, and the duo did not consider Chicago home, otherwise they would have been strong contenders for this list.

**Note – The Impressions as a group were certainly eligible for this list, however their success was largely the work of lead singers Jerry Butler and Curtis Mayfield, both of whom made the list as solo artists and were credited for their work with the legendary group.


By DJ Rob

12 thoughts on “Chicago’s 25 Best Musicians – a Tribute to the Cubs!”
  1. First let me say that I am a HUGE Common fan. However. With ICONS like Chandler, Hathaway and Hancock available I don’t see him being in. Also without Ramsey Lewis there probably wouldn’t be a Earth Wind & Fire. Maurice White got his start as a drummer for Ramsey.

    1. I agree. Common was a stretch, but I gave him the slight edge over those artists. Had I expanded the list to 30 or 40, they would definitely have been included.

  2. Wycc on PBS in Chicago is doing a special on Buddy Guy at 4am on Saturday June 6th… For early birds only. Might have to dvr that. : )

  3. Hello DjRob! I enjoyed going through this list and was totally oblivious that a lot of these great artists were part of Chicago’s music history. Earth, Wind and Fire?? I love that band! Wish I get a chance to see them live some time soon.
    I actually went to see Buddy Guy at Legends in January of this year and it was such a cool show!

    1. Hey Roberto, thanks for the comment! I hope you get to see EWF at some point. Even though they’re not what they were in their prime, it’s still a worthwhile show!

  4. Loved the article, I would have LOVED to see Minnie much higher on the list though, LOVE Fall Out Boy and Earth, Wind & Fire is my all time favorite band……. just exchanging numbers 22 an 12 and the list is WAY more accurate…. just my opinion. GREAT READ
    Marcus Howell

  5. Isnt Cheap Trick from Rockford, IL? Why not include REO Speedwagon from Champaign? Lol.

    But other notables: Twista, Lupe Fiasco.

    1. You’re right, Rockford is a little bit far to be considered a Chicago burb. Unless I or one of the other readers can find a stronger tie to Chicago for Cheap Trick, I may have to eliminate them from the list…unfortunately.

Your thoughts?