Kewl’s Multi-Dimensional Music Matches His Life

By Dylan Deprey

Walking into White’s Barbershop, one finds Octavius Simmons shaping up one of his regulars. The buzzing “zips” and “zaps” are interrupted by rolls of laughter.

Simmons (28) laughs along as he brushes hair from his customer’s neck.

“Looks good Tay,” shouts a patron walking past his chair.

Simmons holds many names. In the shop, he’s Tay. In Milwaukee’s ever-growing hip-hop scene, he is Kewl. To his two daughters, he is dad.

It was a balancing act he was willing to tackle, because it was the life that chose him.

Before Simmons was the trap-flavored neo-soul artist Kewl, he was a kid that fell asleep to the sound of jukebox every night.

Before he was giving some of the finest lineups at White’s Barbershop as Tay the Barber, he was just an artistic kid getting his haircut in the same chairs his clients now.

Growing up, Simmons eclectic music palate grew as he lived above his family’s bar.

“Every time we moved around, I moved with it,” Simmons said. “I ended up finding myself skimming through the music. The jukebox became my friend, and at the end of the day I’d end up putting my own money in just to hear it play.”

While unconsciously building his music catalogue, he was also honing his craft with the clippers.

“Living in this neighborhood I’d just walk over and get my haircut.” Simmons said. “I’m looking at them cutting hair and I’m like, ‘I can do this,’ and I was only 11 or 12.”

He picked up the clippers and never put them down. He began with his younger brother’s hair, and eventually started cutting other neighborhood kids hair on his front porch.

“I’d hang a sign on the gate when I was open and charge $5 for a cut,” Simmons said. “I messed a lot of heads up, and didn’t really know what I was doing. But, it got me where I am today.”

Cool Tay or Kewl

Simmons has been getting back to his clipper roots following the release of his first 6 track project, “The Experience EP” in late 2016. “I told myself to get back to the cutting because I was kind of neglecting my barbering a tad bit. I didn’t want people to think I gave up this for that, because this really got me here,” Simmons said.

Though shows may be on hold for the time being, there is still the encapsulating, genre bending sounds from “The Experience.”

Simmons said this project was the artist he knew he always wanted to be.

Before he was the melodic R&B/Hip-Hop blend Kewl, he was rapper, Cool Tay.

“There wasn’t anything wrong with the name It was the just beginning stages of me finding myself as a rapper,” Simmons said.

He was a naturally cool person, and the name stuck in the streets.

“People in the streets or at shows would be like ‘Hey Cool,’ and drop the Tay. I remember hearing somebody say that you should never give yourself a rap name, somebody else should,” Simmons said.

He was only known as Tay in the barbershop, so he dropped it, and the rest was history.

“The Experience”

“The Experience” is unlike anything Simmon’s has done before. He added a singing element to his music that would elevate him into an arena only few artists can successfully balance.

He said he always knew he aspired to wander into more melodic territories, but was insecure about adding singing to the rapping.

“When I was younger I would sing in the choir, and black history programs. So, it was in my blood,” Simmons said.

Whether it is the 7-minute roller coaster of an intro song, “The Beginning of Forever,” or the rap driven “This Feeling,” Kewl speaks on everything from being the life of the party to overcoming life and death situations in Milwaukee.

“A lot of my clients could be here today and gone tomorrow, and its senseless,” Simmons said.

“I’m really sensitive about what’s around me: my environment, family-wise, relationships with people, love, hate and death,” Simmons said. “But, I like to party. So, you are going to hear the good times and the bad times, and in a different way because I don’t sugar coat it.”

Check out Kewl at https://www.facebook.com/1KEWL/