Tre. Charles would sing to just a handful of barroom listeners, if given the opportunity to make a genuine connection via his meditative songwriting and heartfelt storytelling. “I just have to do it,” the Durham-based, one-time Richmonder says. “I have to express it and get it out.”

Nevertheless, he’s about to perform for a four-figure audience as part of the June 21 installment of Friday Cheers, which features hop-hop legends Digable Planets at the top of the bill. Charles’ set represents the latest step forward in a musical career that began in earnest after a life-threatening 2019 car crash and the clarity of purpose that followed. “Knowing what you want to say and how you want to say it doesn’t come automatically,” he says. “It takes time, and it takes life.”

Charles’ 2023 EP “Currently” is as close to therapy in musical form as you’re likely to find — a four-song distillation of what life had thrown at him and the coping mechanisms that kept him on track. From the relatable realization that defines “Lately” (“Lately I’ve been doing too much / And lately I’m always in a rush”) to the reassuring repetition in his most-streamed song, “Mantra” (“It’ll all work out like right now”), Charles has a gift for turning his inner work outward so that others can benefit. The next challenge? Scaling that emotional impact up while staying true to himself. “I still want to connect with anybody and everybody who wants to connect,” he affirms. “That’s why I do it.”

Seeking connection

Charles moved around growing up and has since embraced a nomadic geographical flexibility. Before relocating to Durham, he spent a formative time living in Richmond and working at the Country Club of Virginia. He also worked the city’s brewery circuit, which tested his sense of musical grounding. “Everybody was asking me to play the ‘Wagon Wheel’ [type of songs]. I can’t do it … My music is slower, moody. It’s not necessarily what you want to hear while you’re drinking a beer, but I think a lot of people connected with it because they were like, ‘Well, I do actually like to hear stuff like this versus just rambunctious music all the time.’”

But resistance to rambunctiousness doesn’t equal reserve, and while Charles has continued playing tight-knit settings — his October set at the Sefton Listening Room was captivatingly intimate — he always envisioned reaching larger audiences. “That’d be so dope,” he remembers thinking of the prospect of playing Friday Cheers. “When I started going into music, just navigating and seeing that as the upper echelon of what I really wanted to do, that was like the apex for me. I was like, ‘I really want to get to that level.’”

Over the last year, Charles has reached higher and higher. As part of the experimental-leaning musical lineup for the True/False Film Fest in Missouri, he rubbed elbows with a number of acts he admires, including Thao, Ben Lamar Gay, R.A.P. Ferreira and They Hate Change. “It was all over the spectrum, as far as the styles and genres, but everybody was very much doing avant-garde type of stuff,” he says. “It was very cool to [be] put in that conversation.”

At an August show in Virginia Beach, he opened for another classic hip-hop group, Arrested Development. Gigs like these have helped counteract occasional pangs of imposter syndrome, and they’ve given Charles the opportunity to pick up pointers from artists who are thriving at more advanced stages of their careers. “Talking to Speech, [founding member of] Arrested Development, he was like, ‘Yeah, it’s another day at work.’ He went up there and jumped into ‘Everyday People,’ and it was easy [for him]. I was like, ‘This is crazy.’”

While downloading professionalism pointers from household names, Charles has also found creative kinship, particularly when it comes to following an internal compass. He praises the way Arrested Development and Digable Planets went against the 1990s mainstream, setting an example that subsequent generations of sociopolitically-conscious rappers have followed. “It was something they wanted to put out that was needed and that people were receptive to because it was honest to them,” he notes. “That’s how I feel about what I’m doing.”

A lot of hugs

While streaming numbers have provided one metric for what’s resonating with his listeners, Charles has found even more immediate — and meaningful — feedback in the live setting. His performances typically incorporate candid storytelling about his accident, the emotional origins of his songs and even strides he’s made in therapy, all in service of his stated goal of helping people “tap into that realm of introspection.” Audience members have responded by letting Charles in on their own internal lives.

“It’s a lot of hugs,” he notes. “I’m giving out a lot of hugs to everybody, too, like some big, strong, swole, grown men being like, ‘I’m going through some things, and I’m glad you’re talking about it …’ I feel like men — Black men in particular — don’t talk about that. They just wear it, and they keep it, and they bottle it up … They bleed on people who didn’t cut them.”

He calls these interactions “humbling.” As he eyes a follow-up to his last EP, Charles plans to double down on the lyrical subject matter he’s explored so far, including one song that addresses directly the car crash that changed his life. “There’s a song called ‘Windows’ that talks about that,” he says. “All the windows were shattered. I was in there and the wind was coming in. I’m trying to paint that in a song.”

Another new song focuses on “adulting and growing up,” as he puts it. Charles has had plenty of logistics on his plate as an independent artist: booking his own shows, lining up accompaniment for bigger gigs and still trying to find time for recording new material. He’d established a tradition of releasing new music each year on his birthday, April 26, but he missed that deadline this year and hopes to have new music out by next April, if not later this year.

In the meantime, Friday Cheers sets the stage for him to further expand his reach and spread his message of artistic integrity. “Just be honest and keep doing what you do,” he says, sharing both a statement of conviction and advice that no up-and-coming artist should ignore. “Keep examining what you’re doing it for. I’m not saying don’t strive for [Friday] Cheers, bigger stages and stuff, but if people haven’t caught on, don’t get discouraged.”

Cheers to that.

Tre. Charles will open for Digable Planets on Brown’s Island for Friday Cheers on June 21. Gates open at 6 p.m., Charles performs at 6:30 p.m. and Digable Planets follows at 8 p.m. Tickets are $10 ($15 at the door) and can be purchased at venturerichmond.com.