Chicago Rapper Kaicrewsade Inspires Everyone Around Him. Including Me.

An introduction to the 21-year-old rapper, community organizer, and jazz fan aiming to shape the future of Chicago while making great music along the way.

“People still love articles, man. Maybe there aren’t as many of us, but we still love reading articles.”

That’s coming from 21-year-old Makhi Miller—Kai for short—from the West Side of Chicago. He’s a rapper (under the name Kaicrewsade), a community organizer, and someone who’s followed Pigeons & Planes and other music publications since his teenage years.

I called him after discovering his song “Chickenscratch!” through a friend. It immediately became one of my most listened to new songs. On the call, I was just looking to get some background info, but we ended up talking about a lot more than music. 

He told me about growing up in Chicago, why he’s organizing open mic nights, and how seeing the rise of artists like Saba, Noname, Smino, and Chance The Rapper helped mold his view of the world and his own surroundings. I told him about things on the Pigeons & Planes side, why music discovery is a challenge today, and how I miss writing articles but it isn’t the priority it used to be.

It’s ironic, because when I spoke to him, I was planning on getting just enough information to make an Instagram post about his latest song. Even though Pigeons & Planes was built off blog posts and editorial features about rising talent, the days of people reading thousands of words about artists they don’t know are long gone. At least that’s what it feels like.

After hearing Kai talk about articles still mattering, even if it’s to a smaller audience, it made me think there may be more than an Instagram post from this conversation. That’s what a conversation with Kai will do to you—when he talks about music, his city, and his community, the passion is contagious. So here we are. Meet Kaicrewsade.

View this video on YouTube

For a lot of young artists, music starts as a hobby or a side project, but Kai recognized early on that music, and the community that rallies around it, had the power to change the trajectory of his life. Now he’s on a mission.

The first pivotal moment came when he was 7 years old. Kai is from the West Side of Chicago, but he has family ties to Mississippi. “In Chicago, there are a lot of country folks also from places like Mississippi, so I grew up with a lot of jazz and soul, and I’ve been around a lot of old folks my whole life. I always saw the jazz influence.” That influence came across loud and clear on A Tribe Called Quest’s 1993 album Midnight Marauders.

Kai was listening to that album at 7, and it made him want to try rapping. That’s when he made his first song, but his big debut didn’t have the impact he hoped for. “My pops told me that shit was ass,” he laughs. “But then he burned me a CD of all the samples on Midnight Marauders and told me, ‘If you want to learn rap, you need to learn this shit first.’ I was 7 years old bro! And he had me listening to Minnie Riperton, Roy Ayers, Jack Wilkins, and Ronnie Foster.” To this day, it has stuck with him. “Jazz is super important to me—I wouldn’t be rapping without it. I don’t want horns and then 808s, I want the whole thing.” 

"[My dad] burned me a CD of all the samples on Midnight Marauders and told me, ‘If you want to learn rap, you need to learn this sh*t first.’ I was 7 years old bro!"

At first, Kai started a group called Crewsade—no deep story behind the name, he just liked to spell words incorrectly and thought it sounded cool—but that fizzled out quickly. He assembled a jazz band and gave it a shot, but it didn’t get very far. “I tried keys, I tried trumpet, but I was trash at both of them.”

Since he already had a bunch of musician friends, he put all of his energy into rapping, and he started going by a modified iteration of his band name: Kaicrewsade. He stays behind the mic now, but he still works with musician friends to craft every song. And, likely thanks to that burned CD that his dad made, the instrumentation is a critical part of the creative process. “At this point in my life, I hate samples,” he says. “All my beats are made from scratch. I work with really talented producers, talented players, a whole hub of musicians.”

Another significant moment came a few years later. This was around the time that Chance The Rapper was coming up in Chicago, and Kai was fascinated by seeing it play out. Where he was from, that kind of thing didn’t happen often. “There’s not much for us to do in this bitch outside of getting in trouble. We didn’t have no major labels, no big movie companies, there was nothing out here in Chicago.”

Chance was getting national recognition during his blog era-fueled rise, but he was also organizing local events in Chicago where creatives could meet up in person and share their work. Kai’s uncle used to go to some of those functions, and one night Kai decided to sneak in to Chance’s open mic night. “It was crazy seeing that. I was 11 or 12 when I seen that shit. Still to this day... Saba, Noname, Chance—I grew up with all that around me. Maybe if I didn’t sneak into the Chance The Rapper event when I was a kid, I wouldn’t be doing what I’m doing.”

"Saba, Noname, Chance—I grew up with all that around me. Maybe if I didn’t sneak into the Chance The Rapper event when I was a kid, I wouldn’t be doing what I’m doing.”

Kai’s music career is still blooming, but for the few years that he’s been releasing music, he’s also been hosting open mic nights and fostering a growing community under the loose theme of Kai’s Poetry Night. It started at his uncle’s work spot as an open mic night where people could share poetry, music, and advice. But it’s always been about more than that. “40 or 50 people sit in a room and can be vulnerable as fuck,” Kai explains. “There are not a lot of safe spaces in Chicago where people can just say what they want, be what they want. It’s very focused on mental health. There were a lot of those spaces when I was younger, but less now. I love my city, I love Chicago, and I need to do something in my city.”

Early on in the process of hosting these meet-ups, Kai realized he was onto something important when one of the attendees came out during an event. “I didn’t even know it was her first time coming out to a group,” Kai says. The next day, that person texted Kai and thanked him. She said that going to his event and coming out to the audience gave her the courage to come out to her own parents.

“This is a safe place for everyone who comes. It’s not a capitalism thing—sometimes vendors will pop up and we don’t charge them. It’s not about making money. We need places like this in Chicago where people can say what they want, be what they want.”

After talking to Kai, I was inspired. Even after just one conversation, I can see why people rally around him and why he’s the kind of person who can bring together dozens of strangers to share their work, open up to each other, and connect. Shit, he motivated me to sit down and write 2,000 words instead of doing a three-slide Instagram post. And he definitely got me more excited to hear what he makes next.

I struggle with questions about how important the person behind the music is. I’ve always been one of those stubborn fans who believes that “iT’s aLL aBoUt tHe MuSic.” If the music moves you, then a person’s character, motives, or identity shouldn’t matter.

Lately I’m starting to question that line of thinking. It’s not a moral dilemma for me, and it's not about judging whether a person is good or bad. It’s more about wanting to know that what I’m listening to was made with intention and care. At the end of the day, music is an expression, and if the person making it doesn’t have anything to express, then what are we even listening to?

Today we’ve got AI bots that can make songs that sound like hits from some of the most popular acts in the world. We’ve heard AI soundalike machines that can pass for Drake or The Weeknd. A lot of people are asking, “Can AI make songs better than humans can?”

Maybe the real question is: Why are so many popular artists making songs that sound like they could be made by AI?

Of course all music is a formula to some extent. For as long as it’s existed, music can be broken down into chord progressions, time signatures, and song structures that come together like building blocks. There’s no denying that it’s part math, or science, or whatever you want to call it. But there’s so much more to it.

I don’t know how to measure the importance of Kai’s passion, intentions, and actions, and how much that affects how we hear the music. But I know that for me, it means a lot. And when I listen to his music now, I listen knowing that all the pieces are there for him to become an artist that can impact others in the ways that Smino, Noname, or Minnie Riperton impacted him. 

That human element matters. It matters that Kai is building hope in his hometown, and it matters that he’s making his beats from scratch. It all speaks to a deeper story of human creation, and how this form of expression can change people’s lives.

Right now, Kaicrewsade only has a handful of songs out on DSPs, but he’s starting to gain some traction. After meeting Chris Classick from Classick Studios by chance at a Danny Brown show, he’s been recording in the rooms where acts like Smino, Monte Booker, Noname, Mick Jenkins, and Chance The Rapper got their starts.

“Kai brings back that 2014-2017 era of Chicago Music—Smino, Noname, Saba, Mick [Jenkins], Chance—and I haven’t gotten that feeling in a while,” Chris says. “Just pure heart and love for the music with jazzy, soulful production. I became a fan. Kai knows where he came from, what he wants, has vision on where he wants to go at such a young age. Also, his work ethic is impeccable. It was like -10 degrees and I saw him shooting a video for his next release.”

Since this all started with Kai sneaking into a Chance The Rapper event as a pre-teen, it only felt right to ask Chance what he thinks about Kai. I sent him the “Chickenscratch!” video and told him some of Kai’s story. 

“When I heard him my first thought was this kid is so different and poised and really a breath of fresh air in terms of sound and hunger coming out of the city,” Chance replied. “But then hearing him shoutout Noname as an influence got me a little teary-eyed. We’re all still kids it feels like; so to be looked up to and loved by this new generation of talented creatives is a validation I never saw coming.”

“When I heard [Kaicrewsade] my first thought was this kid is so different and poised and really a breath of fresh air... But then hearing him shoutout Noname as an influence got me a little teary-eyed. We’re all still kids it feels like; so to be looked up to and loved by this new generation of talented creatives is a validation I never saw coming.” – Chance The Rapper

Kaicrewsade has momentum on his side, and if his track record is any indication, the connections and growth will continue to build. His latest song “Chickenscratch!” is at 20,000 streams on Spotify, making it the biggest song he’s released yet. It’s also his best yet, if you ask me.

Kai isn’t working with major labels or a team of industry professionals. He’s been managing his career on his own, releasing independently through Distrokid and handling the uploads himself. He’s still in the DIY mindset and his buzz might be mostly local for now, but he’s already thinking about the long-run, and his ambition is growing stronger.

“I don’t know about labels right now, but the goal is definitely to make it with music,” he says. “I just wanna have the rawest discography of all time. I want to put jazz at the forefront, and I want people to hear this later on and be like, ‘You made that shit at 20, 21 years old?’ I want discographies like Herbie Hancock, Kamasi Washington, or Robert Glasper.”

He’s aiming to release a project in the summer. “I’m nervous, but it’s okay though. More music, more building.” And of course, when Kai talks about building or making it in music, he isn’t just speaking about streams, label deals, or industry credibility. 

“The world is too fucked up right now to just be dropping songs. I love this shit, I love this more than anything, but we gotta do a lot more. We need to do more than just drop songs, because we have platforms. I did a coat drive at the last event, and I’m trying to get together a toy drive for the kids going back to school in August. I’m definitely going to do more open mic nights too.”

Hopefully a couple of kids sneak in.