Jurassic 5’s Chali 2na: LA Hip-hop Favorite Paints a New Portrait


Chali 2na (Erika Goldring/ Getty)Chali 2na painting his tuna (Screenshot from 2NATV)(Courtesy of Chali 2na)(Courtesy of Chali 2na)(Courtesy of Chali 2na)(Courtesy of Chali 2na)(Courtesy of Chali 2na)

Los Angeles has a soft spot for DIY hip-hop multi-tool artist Chali 2na, who has been entrenched in representing Southland culture since breaking into the national music scene in the 1990s as an MC for Jurassic 5 and Grammy-winning Ozomatli, both of which he co-founded. He’s also had significant success in visual arts, painting, aerosol spray paint, oils, prints, and even colored pencils. As a painter, 2na has a contemporary fine-art style that builds on the foundation of graffiti art, in the form of pieces of his namesake fish swimming down a subway car, or a skeleton-faced Uncle Sam.

The deep-voiced rapper that many know as the “verbal Herman Munster” is leaning to his detailed hand as an artist, creating paintings on commission and for the love of the art. The artworks, signed with “2NA,” are compliments to his rapping abilities that broadcast Jurassic 5’s Southern California vibes — formed in the fertile hip-hop soil of Leimert Park’s Good Life Cafe — to the world. Chali (real name Charles Stewart) has often said he’s an artist first and rapper second, instead of the other way around.

“The small things like attention to detail, patience, my love of putting things together in an interesting way — it all came from painting,” Chali 2na tells LA Weekly. “It’s just expression for me, man. It wasn’t anything else to that. That was my initial introduction to hip-hop, aside from music, was graffiti. I feel like even when people don’t see the things that I paint or don’t know about the time that I spend practicing that craft, it has always been there and will always be. It depends on how my life turns out. But [painting] is a permanent fixture in my life. It stays there only as it becomes a career in the last seven, eight, 10 years, lately. Being able to sell paintings, that’s been a cool thing to be able to do after so many years of pouring myself into this picture that is a canvas.”

2na says, “Now that it’s turned into something lucrative, it’s a beautiful thing at this stage of my life.”

One of his recent paintings, an eight-by-four-foot canvas with a scary, colorful T. rex, is sitting and waiting for a protective covering. Other new paintings include Graciela, a nonagenarian “cigar lady” from Havana, Cuba, who passed away during the COVID pandemic, and a portrait of British reggae singer, Tippa Irie, which graced the cover of Irie’s 2023 memoir Stick to My Roots. A gallery of Chali’s work can be found at chali2na.com.

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(Courtesy of Chali 2na)

2na can be commissioned to paint a mural anywhere in the world for $10,000, as listed on the Jurassic 5 website. Who knew?

The LA graffiti artist Mosh, a member of the OTR and LOD graffiti crews, went to Bancroft Junior High and Marshall High with 2na in the 1980s and remembers him as a creative force. 2na hadn’t yet evolved into becoming a rapper — that would be a surprise for later. He was just an artist who impressed the younger kids with his graffiti black books.

“[2na] was a little older than me, maybe about a year or two older. … One or two years of experience and being ahead of the game made a big difference. He was definitely an influence on the guys who were in 7th and 8th grade,” Mosh tells LA Weekly. “I didn’t know him as a tagger and being out there in the streets, tagging buses like us. He always had that fine art style of colors and blending stuff really nice. That caught our eyes and influenced some of the younger crowd of writers trying to learn what we call ‘the craft.’ We were trying to learn from older guys like [graffiti artist Mike] Pyro and Charlie to give us some tips of what we could do. Seeing their graffiti, you could call it influence, but we were little kids biting styles and trying to slip in a bit, you know.”

2na’s color scheme, as showcased in the works at his 2018 music-art tour “Against the Current,” has brooding shades that distinguish graffiti art — the dark greens of a mysterious tree frog or the black surrounding his face as a half-fish with scales, the latter of which was the cover of his 2009 album Fish Outta Water. He’s humbly painted killer pieces from Sydney to Sao Paulo. But he often enjoys staying within the parameters of portraits.

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(Courtesy of Chali 2na)

“I love portraits, man, shoulder up. You know how people who are sculptors do busts?” he asks. “I like to do portraits in the same [style] – I like to do from shoulder up, the detail in the face. Whether it be an animal or us humans as animals. It’s something about the faces that I love. You can do little things with the background that can enhance what you’re looking at. You can say so much by saying so little.”

Chali’s highly practiced visual arts ability started fortuitously in LA’s graffiti art scene, a free-for-all of artistic energy and personalities that could rival any American city. The future rapper created high-profile pieces at the streets-approved Belmont Tunnel and Pan Pacific Park, both varsity-level competing grounds for the city’s beastliest graffiti artists, with whom he could network. Well-received was his Belmont Tunnel piece, a unicorn-slash-man, co-created by fellow artist Jack Frost, illuminated with whites, purples, and pinks.

Mosh said of the unicorn piece: “It blew a lot of people’s minds away. I recall that exactly. Like, ‘Whoa, whoa, who is this guy?’”

Chali explains, “In one fell swoop, I was able to meet the whole Los Angeles underground graffiti scene. When I met everyone at Pan Pacific Park, I started to see who was who, what was what, which cliques were affiliated with gangs, which cliques were pure artists. I was able to exist within it, without upsetting the balance of anything.”

Fellow LA graffiti artist and hip-hop musician Stroe, a member of several graffiti crews including UTI, and who performs under the name Monstroe, has been writing graffiti in South LA since 1987. Stroe shared the stage a few times years ago with Jurassic 5 as part of his group The Bzerkos, and Chali brings a lot of talent and energy to the scene, Stroe says.

“I’ll say this about Chali 2na — I have great respect for him, what he’s brought to the culture,” Stroe, whose recent music includes collabs with LA vets Ras Kass, Myka 9 and Rakaa Iriscience, tells LA Weekly. “That fool can write and rap dope as fuck.”

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(Screenshot from Instagram @chali_2na)

When Chali arrived in LA in the 1980s as a teenager from Chicago, he took to occasionally tagging his street name as a nod to his old home: sometimes as “Shicago,” and sometimes with the number “1000” at the end. His tag was “2na” when he lived in Chicago.

Although he said he tagged a little in LA, he left the prolific tagging to Triax, Chaka, and Wisk. The detailed art was a more natural fit for the budding artist, who created colored-pencil portraits of Ed Bradley, the “60 Minutes” journalist who won 19 Emmys, and Harold Washington, the first Black mayor of Chicago, the latter with the Chicago skyline in the background.

“It was something I was really, really, really proud of,” Chali said, noting that his gift was encouraged by a teacher with gentle ribbing about his level of detail. “Those two [pieces] came out amazing.”

“There were about three major artists in my family, two of my uncles and one of my aunts,” Chali says. “Two of my uncles were like serious artists, wanting to constantly paint. My dad could draw. He wasn’t really serious about it. He turned his precision into, when it comes to stuff like that, measurements. He became a carpenter-slash-painter. He could build a house with his hands. My uncles were actual pick-up-the-brush, the oils and acrylics. Me sitting there, watching them paint or me painting with them, almost like they were my teachers. [These were] people I looked up to.”

With streaming pushing artist compensation down and a collapsed physical distribution system in the music industry — a much different scenario than when J5 hit the scene with 1997’s EP – the artist’s revenue structure has morphed into using music as advertisements for live concerts, he says. 2na has had a touring system in place for years, traveling the world many times over to do gigs and meet the fans. He’s toured through Europe twice since August, joined by a live band at stops including Zurich, Vienna, Paris and Geneva.

“My career, I’ve increased my touring something crazy because I love to travel and I love to perform,” he says. “I think the love of traveling and performing and the experience of doing it for so many years has taught me how to maximize my output while I’m out there.”

His seminal group, Jurassic 5, is always somewhere in the orbit of potential new musical projects for him, Chali says, noting that the group remains friendly, though J5 hasn’t released a new full-length album in almost 20 years. The crossover sound that put them on national magazine covers and playing to huge festival crowds wasn’t forgotten by fans, who still view the group with nostalgia akin to seeing an old friend.

Mosh says, “I’m still a fan. I was a fan when I was in junior high and I’m still a fan now in my 50s. I dig his stuff, both the art and rapping. Big ups to him. I think he’s evolved as an artist and is doing more fine art stuff. As a true artist, he keeps evolving. I’m big on that.”

2na is doing live shows with his J5 bandmate Cut Chemist. Other J5 members have pursued independent projects. A key part of J5’s sound, Zaakir (Soup), even worked a humble maintenance job in Santa Monica to help make ends meet, according to a 2016 Vice story.

“As far as what’s going on now, I think everybody at this age is pursuing other things. Doing them before it’s done. People are blinking and falling off the Earth. There is no telling what’s going to actually happen,” Chali says. “I’m grateful to my brothers. They’ve led to every success that I’ve had right now, so I appreciate them.”