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Jim DeRogatis

50 Chicago Artists Who Changed Popular Music — Hip-Hop

Our countdown to 50 Chicago artists who changed popular music comes to an end with the scene that is most active and promising today: hip-hop. But Our Town was relatively late in making its mark in this genre compared to the accomplishments on the east and west coasts, or in Atlanta and the Dirty South.

Some will disagree, but for me, the Chicago rappers who first won modest national acclaim were either novelties, like speed-rapper Twista, or didn’t have much to say that was memorable or uniquely Chicago musically or lyrically, like Do or Die and Crucial Conflict. That began to change about two decades into hip-hop’s development with Common; it exploded with Kanye West, and it continues today with Chance the Rapper.

Those three artists — and all but one of the others on this list — not only broke new musical ground, but embodied a distinctive Chicago lyrical outlook that, rather than glamorizing or merely reporting on the nihilism of the thug life, found strength and hope in the communities that have typified all of the great musical scenes we’ve examined here, from the blues to gospel, and from house music to the indie-rock underground.

The city that works is a place where real people come together to make things happen — including great art. And, yes, that even includes that notorious egotist, Kanye.

44. Common

“Hip-hop is supposed to help you elevate, to go higher.”

Born on the South Side and raised in Calumet Heights by his educator mom, Lonnie Rashid Lynn Jr. made his inauspicious debut as Common Sense in 1992 with Can I Borrow a Dollar?, though his amazing abilities as a freestyle rapper garnered more attention at first than his early recordings.

From there, however, Common never stopped growing and evolving, drawing the best from producers such as No I.D. and J Dilla, and collaborators such as Erykah Badu and the Roots, always experimenting and challenging himself and his audience.

At this point, with 11 albums in a mostly stellar discography, it’s hard to even limit the number of high points. His fourth release Like Water for Chocolate (2000) may be the most commercially and critically successful, though my favorite is the wild psychedelia of Electric Circus (2002). And even though he may now be as celebrated for his acting as his rapping, his last album, Black America Again (2016), absolutely is a contender for another of his best. The man was, is and likely always will be an inspiration.

Click here to listen to Common on Sound Opinions in 2006.

45. Kanye West

“I am God's vessel. But my greatest pain in life is that I will never be able to see myself perform live.”

Granted, this is much easier said than done, but forget everything you think you know about Kanye Omari West for a day and go back and listen, really listen, to the eight albums he’s given us to date. You won’t find more ground broken musically or lyrically in hip-hop or in any other genre of popular music, period.

From his early love for Chicago-style soul “dusties,” a passion he shared with his mentor Common, to the rich orchestrations of The College Dropout (2004), and from the wild electronic experimentation of 808s & Heartbreak (2008) to the incredibly dense tapestries of The Life of Pablo (2016), West has proven himself a musical visionary. And he has matched that creativity in his lyrics, baring his soul to rap about subjects few others have dared to explore: his love for his mother, the rush of emotions standing beside his grandmother’s death bed, his own insecurities, and the down sides of the spotlight he is so clearly addicted to.

Sure, it’s a shame that all the noise can drown out his accomplishments as a producer and rapper. But the genius in the music is there. It is undeniable, and it’s really all that matters in the end.

Despite us covering West from the beginning, it’s a major disappointment to Greg Kot and me that we’ve never gotten him to come on Sound Opinions to just talk music. But here’s an interview I did with him in 2005, not long after his infamous dis of then President George W. Bush in the wake of Hurricane Katrina, a subject he addressed with considerable insight, even though his handlers panicked when I asked him (and they’d told me not to).

46. Lupe Fiasco

“I grew up in the hood around prostitutes, drug dealers, killers, and gangbangers … but inside, there was National Geographic magazines and encyclopedias and we watched public television.”

Nearly as charismatic as Common and almost as musically voracious as Kanye, Wasalu Muhammad Jaco has had a much more difficult relationship with the music industry: He’s officially quit three or four times now.

But From his Kanye-assisted breakthrough “Kick, Push,” which I maintain is as wonderful a musical evocation of skateboarding as the Beach Boys’ best tunes were of surfing, to more recent work that rightly positions him as the Noam Chomsky or Howard Zinn of hip-hop, Lupe is the lovably goofy nerd who grew up to become a razor-sharp intellectual and a fearless, committed, but always artful preacher.

Let’s hope this brilliant and very much-needed voice never actually stays retired.

Click here to listen to Lupe on Sound Opinions in 2007.

47. Rhymefest

“When you have a name like Che, it’s definitely something that you have to live up to. How could I be named Che and then do all songs about dancing in the club and who got the fattest ass?”

If you’re looking for hip-hop’s version of Studs Terkel, that quintessentially Chicago voice of the working man, look no further than Che Smith, a.k.a. Rhymefest. 

Like Lupe, Rhymefest has never had the commercial success he deserves on his own, though he did score big by co-writing “Jesus Walks” with Kanye and “Glory” with Common and John Legend. And yes, he failed at politics, during his unsuccessful run for alderman in 2011.

But the artist’s three albums are as real and as strong as hip-hop gets. Onstage, his intensity as a performer can match that of Iggy Pop. And he remains a dedicated community activist and a major inspiration to Chicago’s hip-hop community, as evidenced in the 2015 documentary, In My Father’s House, which I wrote about for this blog.

Click here to listen to Rhymefest on Sound Opinions in 2006.

48. Kid Sister

“When I do music, it’s my goal to create in a way that is as good if not better than any of the guys out there. I never think, ‘I have this responsibility because I’m a woman.’ I think, ‘I have a responsibility to be a bad-ass because I’m a musician and I don’t want to put out crap!’”

Melisa Young, better known as Kid Sister, flies even further under the national radar than Rhymefest, and to date she has only had one major hit: the single “Pro Nails,” which, once again, got an assist from Kanye.

Nevertheless, Kid Sister’s debut album Ultraviolet (2009) is a brilliant — and very Chicago — hip-hop masterpiece.

A notorious perfectionist, as she told me in an interview when that album dropped, she may just be waiting until everything is just right to give us the follow-up. But even if she never records again, she’s as deserving of her place on this list as the Shadows of Knight. There’s no shame in being a one-hit wonder if that hit was as potent as “Pro Nails” and Ultraviolet.

Click here to listen to Kid Sister on Sound Opinions in 2010.

49. Chief Keef

“I’m with the stop the violence campaign, that’s why I paintball now.”

I’ve got more problems with Keith Cozart than anyone on this list beside R. Kelly, primarily because I think the fundamental message of his music is nearly as hateful, as I noted on this blog here.

Make no mistake, judging solely on the energy of the music, drill is an incredibly powerful sound, and Chief Keef remains its finest proponent. But at the risk of sounding old-school or hopelessly clueless, hip-hop is an art form that is also — perhaps more so — about the power of the words. And Keef simply has nothing new or original to say in his one-dimensional portraits of gangster thuggishness.

Yes, Sosa set the music world on its ear for about 10 minutes. But that’s now nearly three years in the past: He was dropped by Interscope Records in 2015 when he failed to move as many units as their equally controversial bestseller Eminem, and he claimed to have retired in 2016, preferring to spend his days playing paintball in a new mansion on the west coast. But I’d love to see him surprise us all — and prove me wrong — by re-emerging with a more mature and complex message as powerful as his music deserves.

50. Chance the Rapper

“There’s a hunger in me that always wants to be creating and orating, telling people something and giving them information and getting feedback. There are so many questions that I’m trying to ask, and I’m still so far from being done saying what I gotta say.”

Chancelor Bennett is the voice that Chicago needs today, more than ever. Irreverent but inspiring, goofy but deadly serious, potent but never preachy, he is all the more effective for being as seductive musically as he is thought-provoking and emotional lyrically.

I could go on — and I have, in blog posts such as this one or this one and in Sound Opinions reviews such as this one and this one — but I’ve basically written a book for this series by this point (any publishers interested?). And I don’t think there’s much more to say other than I think that many of my favorite artists on this list — Curtis Mayfield, the Staple Singers, Mahalia Jackson, Muddy Waters, Frankie Knuckles, Naked Raygun — would hear a lot of themselves and of the Chicago they loved in Chance.

Now turn it up and hear for yourself.

About this series:

In my “other” role as an assistant professor at Columbia College Chicago, I was asked in the fall of 2015 to develop one of several “Big Chicago” classes intended to introduce first-semester students to the rich and diverse culture of Chicago. “Music & Media in Chicago” has made me think long and hard about the passions that have consumed my life. Last summer my editors at WBEZ said, “Hey, we should highlight your overview of Chicago music here!”

In comparison to smaller cities such as Nashville, Memphis, Detroit and Austin, Chicago pays woefully little attention to its musical history, doing little to trumpet the past or celebrate the present for residents or tourists. Mind you, this and every installment of “Chicago Music History 101” is just one critical fan’s take on what is most in need of recognition from our long and rich sonic legacy.

Limiting the series to “50 Chicago Artists Who Changed Popular Music” is completely arbitrary — it could have been 100, or 1,000 — and I’m leaving other genres such as jazz and country to other critics and fans. This overview also is entirely subjective: Every reader and listener can and should have their own list. This simply is a place to get the conversation started.

Special thanks to ace director and videographer Andrew Gill, online majordomo Tricia Bobeda, and former digital intern Jack Howard for all of their help.

Click here for Part One in this series, the Blues.

Click here for Part Two in this series, Chess Records and Early Rock ’n’ Roll.

Click here for Part Three in this series, Gospel.

Click here for Part Four in this series, Rock in the ’60s and ’70s.

Click here for Part Five in this series, Soul and R&B.

Click here for Part Six in this series, House Music.

Click here for Part Seven in this series, Rock in the '80s.

Click here for Part Eight in this series, Alternative Rock.

Follow me on Twitter at @JimDeRogatis, join me on Facebook, and podcast or stream Sound Opinions.

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