As he approaches his debut performance at Lollapalooza, Chicago rapper Kaicrewsade, whose real name is Makhi Miller, carries his hometown’s culture and music legacy with him. The 23-year-old artist, who recently celebrated his birthday and completed a European tour, reflects on a childhood filled with musical influences that shaped his artistry.
Growing up listening to hip-hop giants like Common and Kanye West, Kaicrewsade recalls cherished moments spent with his ‘Pop’ in their truck, cruising through the streets of Chicago. Those drives included trips to Hyde Park for music festivals, where they would peruse through jazz albums at Hyde Park Records.
At home, the sounds of jazz and neo-soul played continuously, thanks to his mother, a music enthusiast from the South. ‘My parents are music lovers,’ Kaicrewsade remarked. ‘I remember being a kid, always just hearing funky bass lines and crazy chords.’
Kaicrewsade’s upbringing in a creative environment included participation in art-focused drum camps, poetry clubs, and jazz bands. Despite moving to Lansing for high school, he often traveled back to Chicago to connect with his musical roots and community.
Inspired by the next generation of Chicago artists like Saba, Smino, and Noname, Kaicrewsade acknowledges the profound influence they had on his growth as an artist. ‘I’ve been listening to Saba since I was a child,’ he shared. ‘Real Chicago rap magic.’
The release of Saba’s mixtape ‘Care for Me’ during Kaicrewsade’s eighth grade left a lasting impression, marking an important phase in his creative development. He views Saba as an older brother figure and credits other artists, like Noname, with enriching his understanding of jazz and deepening his engagement with societal issues.
Expressing pride in Chicago’s musical diversity, Kaicrewsade said, ‘I’ve never heard another rap city do it like us. Everyone’s got their own flavor, but we just have the soul. We got some undeniable juice.’
After years of honing his craft, Kaicrewsade produced his first EP, ‘Steve’s Demo,’ in his car. This project gained attention when it was featured on Lyrical Lemonade’s year-end top 50 list when he was just 16 years old. His hit song ‘Chickenscratch! (Live)’ has amassed over 300,000 streams on Spotify and showcases his signature blend of neo-soul and jazz, exploring themes of young love with catchy melodies.
Now signed to Classick Studios, the same Chicago-based label that nurtured talents like Smino and Noname, Kaicrewsade is committed to creating soulful, authentic music. ‘This is the independent city,’ he emphasized, reflecting on how this collective spirit motivates his work.
He is also passionate about giving back to the community that raised him, having established Kai’s Poetry Club in 2022 as a birthday celebration. This annual event encourages participants to share their poems and discuss mental health openly, inspired by Kaicrewsade’s experiences in college Bible study where people could unite to converse about faith and hope.
Kaicrewsade views poetry as a powerful medium for fostering vulnerability within the Chicago community. ‘Poetry was always cool to me,’ he explained. ‘I thought it was a cool way to create a space of vulnerability for Chicago.’
The latest gathering of Kai’s Poetry Club saw a full house in Pilsen this past February, demonstrating the positive impact of his initiatives. In addition to promoting creative expression, Kaicrewsade continues his community efforts through coat drives during winter and hopes to expand his activism as he releases new music.
The artist is set to unveil his sophomore mixtape, ‘Joint4u!,’ with the release of the single ‘Beeper!!!!.’ This track reaffirms his jazz influences and reflects his experiences traveling to places like Los Angeles and the United Kingdom.
Despite this international inspiration, Kaicrewsade remains rooted in his Chicago origins. ‘It’s a great Chicago project at the end of the day,’ he said, reaffirming his commitment to his city.
While he spent some time outside Chicago for college, his heart remains deeply connected to the environment that shaped him and his musical inspirations. ‘I love Chicago,’ he stated. ‘I got it from my pops. I’m gonna be here forever, probably.’
For Kaicrewsade, performing is his greatest joy, and his upcoming debut at Lollapalooza is not just a professional milestone but also a personal one as it marks his first time attending the festival. Scheduled to perform at The Grove from noon to 12:30 p.m. on Sunday, Kaicrewsade is eager to share his music with a broader audience, continuing to celebrate his roots while looking forward to the future.
image source from：blockclubchicago
