Kanye West Respects R. Kelly’s Chicago Pride Wearing Yeezys In New Prison Photos

BY Bryson "Boom" Paul 7.9K Views
Link Copied to Clipboard!
News: R. Kelly Booking Photo
Feb 22, 2019; Chicago, Il, USA; A handout booking photo provided by the Chicago Police Department of R&B singer R. Kelly who's official name is Robert Kelly. Kelly turned himself in and was arrested after being charged with 10 alleged counts of class two felony criminal sexual abuse ranging from 1998 to 2010. Mandatory Credit: Handout Photo/Chicago Police Department via USA TODAY NETWORK
It’s a Chi-Town thing.

Kanye West continues to cause controversy his tweets. In the latest tweet, the mogul pays respect to the fellow Chicago native and controversial R&B singer R. Kelly for his city pride. A couple of photos surfaced on social media of the singer in good spirits, wearing a pair of Yeezy. Acknowledging the shoes, Kanye tweeted, “My N***a Kells still got that Chicago spirit. They ain't break him. And he got on Yeezy. On you Yeezy over everything.”

In prison for sexual assault, Kelly faces ongoing lawsuits from victims seeking damages. Many plaintiffs allege coercion, manipulation, and abuse spanning decades. His financial assets have dwindled due to mounting legal fees, settlements, and judgments. His legal battles continue, with some survivors still fighting for justice. These lawsuits, combined with his criminal convictions, have cemented his fall from grace as one of the most notorious scandals in music history. The victims have not received awarded settlements from the singer yet. The victims have requested his royalties.

Kanye West & R. Kelly’s Chicago Ties

Kanye West and R. Kelly, two of the most influential yet divisive artists in modern music, are deeply tied to Chicago. The city's rich gospel, soul, and hip-hop traditions shaped their sounds and careers, leaving a lasting mark on the industry. Their careers intersected musically when Kanye produced You Remind Me of Something (Remix) for R. Kelly in 1996. They later collaborated on To the World in 2012. However, as R. Kelly’s legal troubles escalated, Kanye distanced himself. Despite that, he stirred controversy in 2019 by publicly defending Kelly, a move that sparked backlash.

Both artists embody distinct aspects of Chicago’s musical landscape—R. Kelly as an R&B trailblazer and Kanye as a hip-hop innovator. Yet, their legacies remain complicated, overshadowed by personal controversies. Their connection to Chicago is undeniable, but their impact continues to provoke debate, shaping how the city’s musical heritage is remembered.

[Via]

About The Author
Bryson "Boom" Paul has been a contributor for Hot New Hip Hop since 2024. A Dallas-based cultural journalist, he is a CSUB graduate and has interviewed 50 Cent, Jeezy, Tyler, The Creator, Ne-Yo, and others.