Brooklyn-born, Atlanta-raised rapper Gilles doesn’t have the stereotypical hip-hop backstory. There is no hardscrabble history, no illegal hustle here. In fact, the rhymer from ATL’s Buckhead neighborhood was an attorney before he decided to take his musical career to the next level. He explains that he always had the itch to be an emcee, and his time at law school only made it clear that he wasn’t where he wanted to be. “I went to law school, which kind of put a damper in my creative process,” Gilles says.
However, becoming a lawyer was an asset to his hip-hop career. “I got out, passed the bar, and got a job,” he explains. “Being able to do that, now I’m able to do my own thing. Finance myself. We pay for our own videos, website design — it’s all us.”
For the last few years, he’s been intensely focused on his dream. Leaving behind the comforts of a legal career may seem like an unusual risk; but for Gilles, nothing else would’ve made sense. His new project is called “Successfully Lost,” which is how he described his mindset while pursuing a career that he never really wanted. “When I was coming out of law school and trying to think of what was most authentically Gilles — something we didn’t have to fake — it was [my story of] being an attorney and wanting to be a rapper. While I did go to school for several years, all that reading and all that debt — I want to be a rapper, still,” he says. “You tell people you’re a lawyer and you get ‘Wow,’ but that’s not what I want to be me. That’s not my passion. So I’m successfully lost. You tell people you want to be a rapper and everyone says ‘Why would you want to do that? You’re an attorney.’”
He says his struggle mirrors what an entire generation of millennials have gone through during their young adulthood. “I think it speaks to the larger generation. I’m 27. 80s babies and 90s babies know what they want to do but [a lot of us] don’t know how to get there. It’s the dichotomy of doing what you think will allow you to pay your bills and following your dreams and pursue your passion. ‘Successfully lost’ adequately describes a lot of folks; and certainly me–because I’m a rapping lawyer.”
Now that he’s committed himself to music, Gilles has surrounded himself with a dedicated team. He peppers his conversation with “we” and “us,” a testament to the togetherness of him and his people. “We have some brilliant minds on the team and … they believe in me. So we’re trying to get the message out.”
His combination of Southern lyricism, his atypical tastes and history make for an interesting mix of relatability and uniqueness. And Gilles has the one intangible every new artist needs: perseverance. “You have to be very persistent about getting people to give you a chance. A lot of [artists] feel like all the work is in the music. That’s an element of it, but you’re your own business. The work starts after you’ve finished the music,” Gilles says. “Because you’ve got to get it out. That’s always been a challenge. For us, doing work is the thing.”
“And don’t take things personally — don’t be discouraged when people don’t pay attention,” he adds. “People have their own agendas. You want to be able to continue to approach them. If they didn’t see the first video, maybe they’ll see the second video. Every person is somebody you can try to gain to be on your side. Don’t be discouraged by what somebody didn’t do the first time.”