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Black Music Month: Dear Silas wants you to know Mississippi’s got something to say

The master of the viral video drops a new album focusing on self-love

I love Dear Silas. I love Dear Silas like I love Mississippi. Like I love writers Kiese Laymon and Jesmyn Ward and scholar Eddie Glaude for the way they remind us that Mississippi is home to some of the Blackest, most beautiful literary traditions of Richard Wright and Margaret Walker. Like I love activists Arekia Bennett and Asia Brown for reminding us of the civil rights movement legacies of Fannie Lou Hamer and Medgar Evers. I love Dear Silas because he reminds us of the music traditions of B.B. King, Muddy Waters, Crooked Lettaz, 5th Child and Big K.R.I.T. — a reminder that all that Black greatness emerged from a state where it’s least expected, but shouldn’t be.

You don’t love Dear Silas … yet. Chances are you haven’t even heard of him, but you might have seen his work, even if you don’t know it. That viral video of the West African kids dancing to a hip-hop version of “Gullah Gullah Island” a few years ago? That was Dear Silas. The 2018 Dexter cartoon meme that got turned into the song “SKRR SKRR” that everyone was sharing? Yup. The hilarious Hip Hop Harry rap to go with the dances? Another Dear Silas viral clip. There was also the remix to the “Rain” video that he rapped over, that Missy Elliott herself loved. And the “I Ain’t Stressing Today” video that’s become an internet feel-good anthem. Dear Silas has been in the corners of social media for years, but with his upcoming project, It’s Giving SELF LOVE! (out June 24), he’s turning it all into his most complete project yet.

“It’s the best thing I’ve ever made in my life,” Dear Silas, real name Silas Stapleton III, told Andscape. “This is my offering to people to love yourself.”

Dear Silas has had his own battles with depression, insecurity and self-doubt, which is what allows him to channel the positivity needed to create inspirational songs.

“I hated the way I looked,” he said. “I hated the way I sounded. I didn’t like my rap voice. I ain’t like my singing voice. I wanted to be taller, just a whole bunch of stuff. And right now, I’m promoting just loving who you are, being the person that God made you, and understanding that there’s only one you.”

Dear Silas is from Jackson, Mississippi. His musical learnings came from his father, Silas Stapleton Jr., who was an alto sax player. He started Dear Silas out on the piano, then the trumpet, which he’d use to get a scholarship at the University of Louisiana Monroe. Dear Silas would eventually start playing at different venues, including B.B. King’s Blues Club.

While Dear Silas was playing the trumpet, he was also fashioning his rap skills. It was mostly a hobby through high school where he’d pass out mixtapes, brushing off suggestions that he should make music for real. As those suggestions stayed in the back of Dear Silas’ mind, he was also figuring out how to master the internet. He started by uploading comedic videos to YouTube that would also end up receiving hundreds of thousands of views on WorldStarHipHop. At the end of those videos, he’d promote something called Wave Grease, a mixtape. But he didn’t tell followers what it was or even if it was music. They downloaded it off the strength of being fans of his comedy. While they’d appreciate the project, the promotional tactics left a bad taste in Dear Silas’ mouth.

“I still kind of felt like, ‘I’m tricking people into this situation,’ ” he said. “I want people to just walk in on a project on their own and like what I got going.”

That realization caused Dear Silas to change his entire approach — including his name, which used to be Trey Parker. (“My name is Dear Silas because I’m always writing a letter to myself, and speaking out loud to myself to kind of help me get through whatever I’m going through,” he explained.) It also caused him to shift from trying to copy popular trends to focusing on music that felt more true to himself.

“My mind frame was like, ‘I’ve got to have something for the girls. Then I’ve got to have something for the dudes. I got something for the streets, and I’ve got to have something for the club.’ I was all over the place, man, trying to please everybody but myself,” he recalled. 

“Now, what I like talking about is what’s going on with me,” he continued. “I’ve got to just put stuff on the forefront of my brain to just remind me that I’ll get through it.”

The new Dear Silas’ first big internet moment came in 2015 when he dropped “Gullah Gullah Island,” an ode to the popular ’90s kids show about South Carolina’s Gullah culture. In the lead-up to the song’s official release, Dear Silas dropped a short video of the hook playing over a scene of West African kids dancing. The video soon went viral. The song encapsulates the Dear Silas experience. First, it highlights his ability to find internet moments to spread far and wide. But it also speaks to how he taps into nostalgia to connect with his audience.

“I love that a lot of my music is nostalgia-driven,” he said. “I love looking at stuff from when I was still a kid. It keeps me comfortable, and it helps to make me forget about being an adult sometimes.”

The nostalgia is great, but it’s a Trojan horse for what Dear Silas is really doing. In “Gullah Gullah Island,” for instance, he doesn’t just pay homage to a show many grew up with. He uses the song to imagine a Black utopia where police don’t harass us and “where they couldn’t bring crack to the ’hood cuz there ain’t no ’hood.” It’s Afrofuturism tied to the parts of our lives that bring us the most peace.

That’s the Mississippi in him. 

“Everything comes from here,” he said. “Blues, rock ‘n’ roll, you name it. I think it’s important for me to try to tell the story of Mississippi, but also tell the story of where Mississippi is going, and what type of people we’ve got here right now, and what are we doing.”

Dear Silas does all of that with It’s Giving SELF LOVE! Throughout the album, he chews up the worst that can happen to us and spits out affirmations and promises for a better tomorrow. The opening track, “Thank You,” epitomizes that approach as he makes an anthemic love song to his haters, showing appreciation for how they motivate him. (“Enemies had made me lose my sight but you put me right back in that mode,” he croons.) “I Love Me” is a rebuke of self-doubt framed like a self-date. The album’s emotional gut punch comes on “March 28th,” a song about losing his father. While the grief is palpable and the devastation nearly overwhelming, he synthesizes that into a loving message about what his father’s greatness portends for future generations of his family. “I’m my daddy’s son, I can’t lie I’m one proud son of a gun/my daddy was clever but I gotta tell ya, Silas Stapleton III gonna be way better,” he raps.

SELF LOVE! is Dear Silas’ most complete work and one of the best albums to release this year. More importantly, it’s a balm. A declaration of a better life. And the type of project that gets us through tough times.

“I’m talking about where I come from on this album,” he said. “This is my biggest attempt yet to let people know that we can stand with the best of them, if not in front of them.”

David Dennis Jr. is a senior writer at Andscape and an American Mosaic Journalism Prize recipient. His book, The Movement Made Us, will be released in 2022. David is a graduate of Davidson College.