Chali 2na is a born storyteller. Gifted with one of the most iconic voices in the history of hip-hop — a deep, rich baritone that rides over the groove and pulls you in with gravitational force — the Jurassic 5 and Ozomatli emcee breaks into a smile as he begins to tell his greatest story of all: the story of his life.

Born Charles Stewart, the Chicago-born wordsmith rose to fame in the late 1990s and early 2000s with Jurassic 5 as part of a wave of alternative hip-hop groups coming out of Los Angeles. He has performed all over the world, reaching Gold status in the United Kingdom for the group’s 1998 debut album. His first love, though, was breakdancing and graffiti.

“Living in Chicago, we didn’t know too many people who were involved in the culture yet, and Chicago was house music central … we were trying to be little outsider kinda cats, so when hip-hop came, it was that outlet,” he says. “The pursuit of that outlet led us to the North side, and we met some of the craziest breakdance cats on Earth.”

2na remembers Chicago’s South Side as a place filled with gangs and drugs in the mid-to-late 1970s — influences he sought to avoid and found an escape from in hip-hop.

“It was easy to just get sucked into that – especially where I [grew up]. So to have something that I was able to occupy my time with that was creative, it was something that drove me,” says 2na.

“Living in Chicago, we didn’t know too many people who were involved in the culture yet, and Chicago was house music central … we were trying to be little outsider kinda cats, so when hip-hop came, it was that outlet.” – Chali 2na

When “Rapper’s Delight” came out in 1979, 2na recalls his entire school memorizing the lyrics. Half a country removed from the epicentre of it all, he would visit the library in Chicago to read up on the growth of the culture in New York City: breakdancing, graffiti, music, you name it.

“Whatever [hip-hop culture] was associated with, we’d go and try to suss out where that is,” he says. “Oh, I heard the graffiti writers’ corner is this train station. It was like a treasure hunt, man, and I loved that.”

When 2na’s family picked up and moved to Los Angeles, he carried a piece of his hometown with him, tagging building walls with the moniker ‘Chicago 1000’ — a nod to the legendary New York-based street artist Futura 2000.

“I figured if he’s 2000, I’ll be 1000,” says 2na. “So that was my form of rebellion at the time: tagging ‘Chicago’ all over LA.”

Los Angeles opened his eyes to an entirely new world of hip-hop culture, where groups like the Souls of Mischief and Pharcyde would soon make a name for themselves. At the centre of it all was a health food store at the corner of Crenshaw Blvd and Exposition Blvd that held a weekly open mic night drawing artists from all over the city: the Good Life Cafe. On Thursday nights, the place would fill with listeners and artists could sign up to perform one song. It served as a trial by fire for many artists, as the crowd wouldn’t hesitate to interrupt a poor performance.

“They had a chant: ‘please pass the mic.’ They would chant; they wouldn’t let you finish [your performance]; the plug would get pulled on you; all kind of stuff.” – Chali 2na

“You’d try to see if you could strategically place your name and hope that they get to you. You didn’t want to be first, but you didn’t want to be last; you wanted to be somewhere in the middle where [the venue] is packed,” says 2na. “They had a chant: ‘please pass the mic.’ They would chant; they wouldn’t let you finish [your performance]; the plug would get pulled on you; all kind of stuff.”

It was there that Jurassic 5 began — a fusion between two groups at the time: Rebels of Rhythm and the Unity Committee. It started as a collaboration on one song, “Unified Rebelution,” which the group debuted on a Thursday night.

“Nobody saw it coming — at all,” says 2na. “We [acted] like we were showing up as usual and just coming to the Good Life to chill and watch; we didn’t tell [anybody] we were going to perform. [So then they say], ‘Okay, so next we got… I guess a new person; I’ve never heard of this one before. Unified Rebelution. Unified Rebelution, y’all in the house?’ All of us got up on the stage, and everybody was like “OHHH S–T.” We did “Unified Rebelution”, and the rest is history.”

So began a four-album run that would carry 2na and Jurassic 5 around the world, reaching as high as #15 on the Billboard 200 chart. 2na continues to tour and release music to this day, having put out a solo studio album in 2009 and four EPs since 2012.

“This is something that we stumbled on, and for people to hold it so dear to their hearts is amazing to me. I’m honoured to be a part of that,” he says.

This interview is originally from a 2013 conversation in London, Ontario for The Come Up Show.