Freedom Thursday is always a vibe, but what vibe will it be? This week the Ride took me home to Chicago, but I wanted to tell more than one side of the city.
I started with Kanye West and André 3000’s “Life Of The Party.” I’ve always loved the ending with DMX talking his daughter through her fear on a roller coaster. As a father, that part hits me differently. From there we went south to North Carolina. Petey Pablo had us swinging T-shirts with “Raise Up,” then Phonte reminded everybody that North Carolina has BARS too with “So Help Me God.”
After that, we dug in. MIKE & Mike Shabb, Odd Future, Slaughterhouse, Inspectah Deck, CRIMEAPPLE with Big Ghost Ltd., then Apollo Brown & Joell Ortiz. Just BARS.
Then I flew back to CHICAGO and didn’t leave.
I started with the rougher side of the city, because when people outside Chicago talk about our Hip Hop, the conversation often lands on Drill, the streets and the violence. G Herbo, King Von, Lil Bibby and Lil Durk gave us that side of the story. But Chicago Hip Hop didn’t begin there, and it definitely doesn’t end there. I closed the first hour by reaching back to Infamous Syndicate, Shawnna and Teefa, with Kanye West on “What You Do To Me.”
Hour two was about showing another Chicago.
Iomos Marad & Zzaje opened that door with “Straight Out Chicago,” bringing knowledge into the Ride. Then Chance the Rapper and Joey Purp took us into the SaveMoney generation. Brittney Carter, Noname, Add-2, Vic Mensa, Milly Mango and Mikkey Halsted kept showing just how many different voices can come from the same city.
Then another SaveMoney connection helped me move from Chicago Hip Hop into Chicago Soul.
And when Chicago starts talking about voices, we’re talking HEAVYWEIGHTS. Ravyn Lenae with Steve Lacy, Jennifer Hudson and Syleena Johnson took us deeper into the Soul before I reached for two generations of Chicago royalty, Chaka Khan and Natalie Cole.
That’s the Chicago I wanted on this show. The hard side is real. The violence is real. The bars are real. But so are the knowledge, creativity, love, Soul and history. Chicago has never been just one story.
Freedom Thursday is always a vibe! It’s just WHAT vibe will it be? This is why you listen. You can’t WIN unless you play!

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