At the end of last year, the musician Charles Singletary, who performs as Charlés, released Thoughts That Roam 2, a 10-track concept project that offers listeners updated access into his subconscious. It wasn’t the first time that the 25-year-old rapper and songwriter, formerly known as Charles DaBeast, has shared scattered thoughts about insecurity, grief, and resilience. Thoughts That Roam 2 is a follow-up to 2018’s Thoughts That Roam.

The New York-born, Durham-raised artist began making music soon after joining a rock band at the age of nine. His time in the band strengthened his skills as a writer and influenced his decision to join the school band. By age 14 he had already mastered playing both the guitar and the trumpet and found a new affinity for hip-hop.

“When I really started rapping, that was during the blog/mixtape era,” Charlés says. “I’m talking J. Cole, Wale, Big Sean, and a whole bunch of underground guys.”

It was an era that molded his initial sound, but because his musical palette remained diverse, transitioning to writing R&B songs with a hip-hop influence came easy.

Thoughts That Roam 2 captures a wide range of emotions Charlés experienced over the past two years, and this time around, he took a more “go with the flow” creative approach. In doing so, he created a project where each track offers something new, sonically.

“I view this project as me just expressing myself in different ways. Whether [the song structure] is melodic or lyrical, or whether I created a pop song, R&B song, or a boom-bap song, I allowed my music to be free-flowing,” Charlés says. He has a name for this kind of music: head music. For Charlés, head music creates a song that prioritizes communicating honest feelings versus following the trends of today’s musical landscape and chasing a radio-approved hit.

Charlés acknowledges that he’s in a real rap mode.

Track 1, “Becoming,” and track 8, “Too Deep for the Outro,” are his favorites, he says.

“I’m not listening to as much melodic music. Some of the more melodic songs don’t really capture my energy at the moment,” he says. It’s a good thing he has the foresight to craft a project that can capture more than just one type of mood.

Frequent collaborator TrizzyBeat$—a childhood friend and Durham producer—also helped Charlés craft a vibe specific for each track.

“We have a similar taste in music where [our interests] are really broad,” Charlés says. “He did eight out of 10 out of the songs on Thoughts That Roam 2. The first time he produced for me was on Thoughts That Roam. Before COVID we sat down and worked together on tracks and intentionally created a sound, but as time went on, and we got deeper into the pandemic, I kind of had to go on my own to record and write by myself.”

Engineers Chris West and Adam Zavala also contributed to the project, and Charlés credits the duo for changing the way he makes music by facilitating a structured and creative atmosphere.

He compares his sound to soul music disguised as “pop-rap,” which blends elements of rap, pop, and R&B. He is dedicated to searching through his past and finding unique ways to tell his stories. Even when rapping about the most universal experiences, he finds ways to make them personable and humorous.

“At this moment, I’m really just trying to figure out the other end of music that doesn’t include the creative process,” he says. “I’m always creating. My attention now is on the marketing side, so people can expect more visuals and interviews. Basically, anything that allows me to push my music further and expand my audience.”

Now that two high-quality EPs have landed Charlés opportunities like opening up for Rico Nasty, he’s ready to enhance his marketing tactics.

“I’ve had a couple of records do pretty well at different times in my career,” he says. “One record gave me the ability to open up for Rico Nasty. But for some of the other records, I feel like I could have done better or been bigger if I had access to quality marketing, especially visuals. Visuals is something I’m really committed to getting ahold of.”

Following in the footsteps of those he admires, like J. Cole and Kendrick Lamar, he’s also been thinking ahead about what his debut studio album would sound like.

“Thoughts That Roam was definitely a project, and this one especially [Thoughts That Roam 2] is like an album, based on how I was intentional, but there’s [still] the debut album that I’m preparing for,” he says. “Kendrick had Section.80 as an album, but Good Kid, M.A.A.D City was the in-studio album. For me, that’s also what I’m working on. Making connections to obtain these dream collabs with other artists and producers. I feel like I will always continue to develop and remix my sound so that it stands out and doesn’t sound like anything else.”

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