Chastain Middle School sixth grader Silas Stapleton III watched his classmates go up one-by-one to pick an instrument for band class on the first day of the school year in Jackson, Mississippi. He had his eye on playing the saxophone so that he could be like his dad, who plays the woodwind instrument. Internally, the 12-year-old was overly confident that the sax was destined to be his, so when the teacher called him up to pick next, he didn’t expect what happened next. 

Walking to the front of the classroom and picking up the brass saxophone, Stapleton adjusted the neck strap, placed his lips around the mouthpiece, and situated his fingers on the keys. Taking a deep breath, he blew into the saxophone, only for no sound to emerge from its bell. Panic set in. “What will my dad think?” he thought to himself.

Sensing his embarrassment, the band director suggested he try the trumpet, holding out the instrument for him. After sealing his lips to the metal mouthpiece and adjusting his fingers on the finger buttons, he pursed and buzzed his lips, successfully producing sound.

“That’s it,” the band instructor affirmed. 

Silas shook his head in disagreement, arguing that he’s supposed to play the saxophone because his dad plays. Unfortunately, his band director disagreed and assigned him the trumpet. How was he going to tell his dad that he failed, he wondered. That thought plagued him throughout the school day. When he arrived home, it was with his head down. He found his dad in the living room. 

“They gave me the trumpet,” he told his father. 

“That’s what I wanted you to play,” Silas Stapleton Jr. responded, surprising his son.

The middle schooler expected disappointment, but was relieved to be met with excitement. His father’s encouragement followed him through life as he eventually began rapping and making his own music. Stapleton Jr. would often tell his son to incorporate his trumpet into his music, but he would dismiss the notion. 

“I was like, ‘Don’t nobody wanna hear nobody rap and play trumpet,’” the rapper negated. 

Dear Silas, dressed in all brown and playing the trumpet
As a kid, Dear Silas wanted to play the saxophone like his father, but fate steered him toward the trumpet. His dad always encouraged him to use it in his music, but Silas rejected the idea for years before finally releasing his new double album notably featuring the trumpet. Photo by Will Willoughby

Today, Dear Silas is in fact both rapping and playing the trumpet on his sixth studio album “SophistiRatchet: RED and BLUE,” which he released on Aug. 28, 2026. Through the double-disk album, the rapper taps into his musicianship by incorporating the trumpet alongside his rapping to create “one big country ball of excellence”. 

“ It sounds like the pain, the struggle, the love, the culture, the food, and the essence and the air of Mississippi. That’s what it sound like. Everything about it is Mississippi. It’s jazz, it’s blues, it’s hip-hop,” Silas described to the Mississippi Free Press. 

Silas credits his mother for his eclectic music taste because she played different genres around the house. Blues, rock, pop, soul and country are some of the genres that influence the type of music he creates today. Watching his father practice his saxophone around the house taught him discipline and consistency, he said.

During his high-school years, Stapleton took an interest in rapping, but didn’t think he had the background to be taken seriously. He settled on the idea of being a music producer instead. Then, Kanye West entered the rap landscape and changed everything for him. 

“He just went the opposite of every norm that you could think of,” the Jackson-native rapper said. “He ain’t rapping about none of that stuff they rapping about, but he around all the guys that’s rapping about that type of stuff. And he got a pink polo on. It’s more accepted now to wear that. But back then, with the collar popped in hip hop, it was a strange thing to people.”

Dear Silas, dressed in all brown and seated with a trumpet in his lap
Kanye West was a huge inspiration for Dear Silas, as his work demonstrated that rappers didn’t have to write lyrics about certain topics or dress a certain way to be taken seriously as a rapper. Silas realized that he could be different from the norm and still be successful. Photo by Will Willoughby

Kanye West’s uniqueness reassured Silas that he could authentically be himself and still be taken seriously as a rapper. He took on the rap name Trey Parker, which combined his nickname, Trey, with the surname of saxophone player Charlie Parker. The rapper defines this era as him doing his best Lil Wayne impression. 

“I appreciate this era because it got me where I am now,” he said. “But at the same time, it was me really dismissing who I was internally because I think around that time I was really trying to make music for what I thought people would like. I gotta have something for the club. I gotta have something for the girls. I gotta have something for the streets.”

He’d often end his projects with two songs that really showcased his musicality and the music he was really into. It wasn’t until someone pointed out that he should make more music like that, that he realized he wasn’t living up to his full potential. 

“Well damn, why am I wasting time making 80% of the album in a different way than what I would actually wanna do?” he asked himself. The creative changes that followed led to his current musical identity as Dear Silas. 

Stapleton attended the University of Louisiana Monroe to study music. After switching his major, however, he lost his full-ride scholarship. He began taking out loans to cover tuition costs for the semester, but he didn’t raise enough. Unable to continue his higher education, he was forced to withdraw from ULM and return to Jackson.

In this interview—presented in a Q&A format—the rapper discusses coming home, his new album, what “sophistiratchet” means, reinvention, and the rise of Mississippi’s hip-hop scene. 

You quit school and you come back home. What happens after that? 

“ I decided to start over and just kinda like get rid of the whole Trey Parker moniker. I was doing comedy videos at the time, too, and that was really just to promote the music. But I also kinda looked at it as if I wasn’t being as confident as I needed to be in my musicianship. Like, I literally been doing this my whole life, and I feel like I need this other thing to help propel it. 

And so I just decided (that) I’m gonna just start from scratch, and that’s when I changed my name back, which is my government name, to Silas. I was like, ‘I’m gonna just start from the bottom.’ And I feel like even though I had garnered so much success under that name, I feel like if you really meant to do this, and if you really believe in yourself, you won’t mind casting aside all of this other stuff and starting fresh. That’s what I did, and it worked out.”

So is that how we get “The Day I Died”? 

“ That’s exactly how you get ‘The Day I Died.’ That is me just really realizing what I was doing was not true to me and not true to where I wanted to go and just the type of music I wanted to make. I feel like ‘The Day I Died’ is like the day I just kind of forsake myself and I gave up on my true intentions and who I really was in order to get all this other stuff that ultimately didn’t end up mattering because I started over anyway. So it was just a rebirth of me and kinda just being reincarnated.”

 You mentioned comedy. Did you do stand-up as well or was it just kinda like skits?

“ I feel like I’m one of the forefathers of what you see today on social media as far as content creation. I was doing it back then and … we didn’t have Instagram, TikTok, which you can upload this stuff to. But I was regularly on WorldstarHipHop like every week for the stuff that I was making, and that was like a viral website. And YouTube, of course, like that’s kinda where I started everything. I was using that to just do skits and just to promote the music.”

Dear Silas, dressed in all brown and holding a trumpet
Anime and cartoons have had a huge influence on Dear Silas, who can draw well and had dreams of being a cartoonist as a child. His 2018 viral hit song “Skrr Skrr” gained even more popularity after someone laid the sound over a “Dexter’s Laboratory” meme. Photo by Will Willoughby

 Are there any similarities when it comes to how you prepare to make your skits and how you prepare for a song? ‘Cause I feel like there’s a level of wit and writing involved with both of those. 

“ When it comes to creating anything, I look at the whole picture. When I’m in the booth, like if I’m rapping, I’m thinking about how this is gonna resonate or translate to the stage. I’m thinking about like, ‘OK, when I rap this part, ’cause I like to be energetic when I do my live shows, I don’t wanna just like rap over the lyrics or the vocals,’ ’cause I feel like you can get that in the car or you can get that in your phone. 

I like to really, really, really, really be hype. So I think to myself, ‘Can I rap it while I’m running full speed?’ Or also when I’m creating music, I’m thinking … ‘What is this gonna look like in a music video? What is the album art gonna look like? What colors do I see when I’m actually performing this?’ And so that’s kinda my world of creation. I’m using every little thing and every aspect to enhance what I’m putting down on wax. So it’s kinda all happening simultaneously. “

 I did notice the Naruto reference on “The Day I Died” album cover, and I kinda wanna know: What impact do anime and cartoons have on your creative process? 

 ”A lot. … When I was younger, I wanted to be a cartoonist. I didn’t wanna be a musician. I wanted to have my own cartoon on Nickelodeon one day. So cartoons (and) anime, especially with anime, just the themes of not giving up, determination, (resonate). 

For Naruto, it was more so of me having like a village of people behind me because I’m so used to doing a lot of everything by myself and not trusting people to get the job done. But I had to kinda learn that you can be great alone, but man, you can be out of this world with a great team. And it kinda taught me to just understand that it takes a village to go the distance. And so that’s kinda what I took from that aspect.”

 You had a viral hit in 2018 with “Skrr Skrr,” and I know it was attached to a “Dexter’s Laboratory” meme. What did you learn from that period in making sure that people didn’t just associate you with that one meme, and that they would kinda come back to see what else you had to offer? 

“ Oh, man. Just leaning into trusting myself. Just trusting my instincts and trusting that I could get people there on my own. That’s kind of what I’m doing right now. I always just make sure that I’m visible, and now I got a record we just dropped from the project, and (it’s) going crazy, blowing the roof off, basically, of what you just said. I’ve been going viral for so, so long. But, it’s also about being able to captivate and maintain the people past the song and them really getting to you as an artist. 

For that experience, I would say the thing I learned the most was not being afraid to promote your song over and over and over and over again—because even at that phase, I was still in my head being worried about annoying people by putting my music out every single day. So I didn’t even really promote that song the way it should have been promoted at the time. It just did what it did because it did what it did. But I learned that you gotta be unapologetic about what it is you do.”

Dear Silas seen seated facing away from the viewer in the yard, beyond a clothing line
“Sophitiratchet: RED” shows the rapper’s confidence in his ability as well as his trumpet-playing skills, which are infused in every song on the eight-track album. Photo by Will Willoughby

You were signed to RCA Records in 2018.  What did you learn from that experience that you’re taking now with you as an independent artist? 

“ Again, to trust myself. I went into that situation, and I kinda felt overwhelmed, and I felt very, very unsure of myself because you walk into a building and you’re in these board meetings with a lot of people and they deal with huge artists every day. You might be sitting in one room and Chris Brown walks past in another room and it’s like, “Oh, I’m on the same label as Alicia Keys and all these other people. And you think, ‘Who am I? What can I do?’ So you start to second guess your decision-making. 

And there was a lot of things that I wanted to do during that era that the label would be like, ‘Ah, we think you should do this.’ And I would say, ‘You know what? They know better than me, right?’ But, I learned later on that they did not know. And if I remember back, what got me here to this label was decisions that I made, and I forgot that. It also just taught me that I know what I’m doing and that ultimately, if I need to, I can do it on my own.”

Segue-ing into the album, you describe sophistiratchet as “the refusal to choose between refinement and authenticity—being unapologetically yourself without conforming to anyone’s expectations.” Have you been in a situation where you were being yourself and felt like you were being policed or forced to conform? And how do you deal with stuff like that? 

“ I think everybody goes through that. Somebody at some point in your life is gonna want you to perform or be something that you’re not. Even when I decided to change my name, I had a lot of pushback from a lot of people because they were just like, ‘Man, why would you do that? Like, you got this amount of views on this or everybody know you as this. You gonna ruin your career. You not gonna be able to bounce back.’ Now I’m like 100 million times bigger than I ever was as that name. But if I had listened to those people, I wouldn’t even be in the situation I am right now. 

The label wanted to make me a R&B singer. And I love R&B, but I’m a rapper and a trumpet player. They wanted me to dress a certain way. I didn’t wanna do it. The headband was a problem for them at one point, even though I don’t wear it anymore. I’ve evolved since then. Those are just certain instances where people tried to get me to do something different, and I don’t give myself enough credit in just being able to stick to my guns on a lot of things. 

I had a record called “I Ain’t Stressing Today,” and I did a dance to it. One of my peers hit me up and he was like, ‘Man, that sh-t was weird. Why you keep doing that sh-t? That sh-t lame.’ But then the sh-t started working and he was like, “Oh, OK, I get it.” But only after you see it working do you get it. I like to look at myself as a pioneer of some sort when it comes to stuff like that because it’s a lot of stuff I’ve done in Mississippi first and a lot of people call me weird for it.”

One album is rapping, and the other one is trumpet playing, which I think is so interesting when I think back to double albums across hip-hop. Can you tell me the significance of the colors for each album and what went into the decision to do your double album like that? What do you want the blue album to communicate that the red album doesn’t? 

“ So the trumpet album was very, very was scary for me to even approach. … I put my horn down for years to the point where I wasn’t even really picking it up but every six months or so. I feel like my skills kinda regressed and I would only use it in instances where I feel comfortable.  And so the original name for (the album) was “I’’m Scared, But I’ma Do It Anyway.” I just really wanted people to understand that if you want sh-t to happen in life, man, you really gotta be action-oriented, and you can’t wait on everything to become perfect all the time. There’s no such thing as the perfect time, the perfect day, and the perfect way. 

My manager and my wife Cookie (had) been begging me to do it forever, and I was like, ‘Nah, nah,’ or, I’ma do it, but I’ma do it when I gotta practice more.’ And I just started to realize that day may never come when you’re making up those types of excuses. 

I had an interview with Estelle, the singer.  We was just talking about other stuff, and she just randomly said, ‘So when are you going to do a trumpet album?’ Mind you, we hadn’t talked about no trumpet stuff, and I was like, ‘You know what? Damn.’ And I looked over at Cookie, and she looked at me like. She rolled her eyes like, ‘Hmm, I told you.’ I said, ‘Yo, I’m doing it. I’m doing a song.’ And I just kinda held myself to it at that point. 

But to kinda go back to your question, it’s actually horn all throughout ‘Sophisticated Red,’ too.  But, I just wanted to prove that I could hold my own with just the trumpet on an entire project, even though I didn’t feel 100% confident that I could. As far as the red and the blue, I feel like blue is more serene. The color just reminds me of just something smooth and jazz. I think blue is more of a reflective color. And when I did the red, red is confidence.  It’s just in your face, and I know like when it comes to rapping, that’s how I feel. I feel like ain’t nobody better than me. I feel like I can do whatever I wanna do when I wanna do it.”

With ‘SophistiRatchet:Blue,’ what experiences were you pulling from when you were playing your trumpet? 

“The crazy thing is when I did these records, I booked a cabin and went into the cabin for like a couple of weeks just secluded by myself—no cell phone service. (I) took all my recording equipment, and I just recorded in the middle of the woods. I didn’t want any distractions.

I always wanna showcase my people (in my music).  When I think about stuff like stretch marks, they show up on us differently. On every one of my projects in some form or fashion, I gotta big up Black women every chance I get. For the generations that come before, you don’t always get to see an example of yourself on a TV screen. And if you got these commercials telling you, ‘Oh, this is a top model, or this is what beautiful is, or this is what high fashion is,’ and the lady or the man don’t never look like you, then you start to feel like, ‘OK, that’s what I need to look like.’

And I felt like that a lot growing up. I hated my skin color. I hated how dark I was. I literally would avoid going out in the sun for too long because I didn’t wanna get too dark. I just felt like I was brainwashed, and I had to kind of reteach myself a lot of things and learn to love myself.”

An extreme closeup of Dear Silas' mouth, showing off his golden teeth art
Dear Silas was nervous about recording “SophistiRatchet: BLUE” because he had not kept up with his trumpet playing over the years, causing him to regress in skill. He recorded the five-track album at a cabin in the woods with no distractions, just Silas and his trumpet, which let him practice and record until he had a product that measured up to his own expectations for the album. Photo by Will Willoughby

 You said one of the songs is blowing up. Which one is it? 

“IDGAF.”

 Why do you think people are resonating so much with that song?

“ Well, one, it’s the most content I put out for one of the records. I feel like all of the records, everybody will deeply resonate with. That’s how they discover songs now. They discover them through visual aspects, so I think the video is helping out a lot.  …  My name is Dear Silas ’cause typically when I make a song, if you hear me saying something, it’s ’cause I’m talking to me. It’s because I’m literally going through that right now; I’m writing myself the letter. So on that day, sometimes I think we put too much pressure on ourselves to exceed all our limitations every single time. Sometimes you gotta think, ‘Nah, it’s OK to fall short sometimes,’ especially if you was giving your all.”

That’s  actually one of my favorites. It’s that little three-song run with that, “Too Cool” and “We Got the Strip Club at the House.” The title is so funny to me because it’s so Black. It sounds like when your mama says, “We got McDonald’s at the house.” And like you said, it celebrates Black women. 

“ When I was making it, I was thinking about like, bro, it feel like a dance song. And I feel like I wanna throw some money, but I’m gonna throw it on my old lady. I ain’t gonna throw it on nobody random. She been working hard. She been doing her thing. She been holding me up and down and all around. I’m finna pay you, give you that money. So yeah, we got McDonald’s at home. We got the strip club at the home.” 

You show a lot of personality in your music like on “Too Cool” when you’re playing your trumpet and you get really excited.  

“ Man, you bringing up all the parts that I be hoping is gonna translate over. I was in my home studio when I recorded that part, and I was literally just getting excited. Sometimes I would just lay my horn parts down, and I’ll improvise those. I literally played it. I was like, ‘Da, da, da,’ and I was like, ‘Oh, sh-t. I like that.’ That’s me in real time figuring out where I wanna go with this and having fun with it.”

What place were you in when you recorded “You Are Enough”? You mention imposter syndrome, so what causes you to feel that way? There’s a lot of interesting things that happen on that song and it feels like you just went into the booth and freestyled.

“ I was going through it when I made that song. At the time, it was called ‘One Take Freestyle.’ If you really pay attention, I was even fighting for words. I was gonna go back and clean it up. But I was like, ‘Nah, it was raw emotion. I’m not gonna mess with it.’

I think (imposter syndrome) is human. It’s one of the aspects about being human that I hate, you know? But you still wanna be human because it’s the essence of who we are. But comparison, it’s the thief of joy. It’s just one of them things where it’s especially hard as a musician or entertainer because you kind of put your whole life out there for everybody to dissect and pick apart. And people are nasty, man. They say bad things to you. 

I’m getting better as far as just really not comparing myself, but sometimes, it’s hard because my job is literally to make something that people will resonate with. … Even if I woke up today and I decided I’m not gonna compare myself to nobody, 100,000 people are gonna do it as soon as they pick up their phone.  

And I gotta make a decision on whether I’m gonna let that get to me, bother me, or I’m not. And lately, what I’ve been doing is, I just acknowledge it. Like if something happened and bothered me, I say, ‘OK, it happened. I didn’t like how it felt, but I gotta move forward.’ And that’s been helping me out a lot.”

Dear Silas, in red hair wrap and white tank top, stands outside in front of a clothes line, pointing to his golden trumpet tooth art
Dear Silas said his album is a good example of what Mississippi hip-hop can sound like. By working together, he added, Mississippi talent can help put the rest of the world on notice. Photo by Will Willoughby

 What are your favorite songs from the album? 

“ Of course, all of them. But, if I just had to choose something right now, I just love when “IDGAF” rolls into ‘Too Cool’ and I come in with the horn. That’s something that gives me hype every single time. 

I really like the storytelling aspect of ‘Pull Up.’ I had a line where I was saying ‘You think ’cause you from up north that it don’t get dirty like it do in the South? N-gga please. For the right amount of cheese, you’ll get sold out for a Jordan drop in ’93.’ Like, just letting n-ggas know racism is not regional, you feel me? It does not only exist in Mississippi. I just hate that narrative that they try to paint on people from Mississippi. And I’m not saying that stuff don’t happen here. I’m not naive. At the same time, though, we much more than that.”

 People love to stereotype Mississippi. Do you get that a lot when you introduce yourself to people and tell them you’re from here? 

“What I hate is when I say I’m from Mississippi, they almost don’t believe it. ‘You can’t be from Mississippi,’ and I’m like, ‘Why can’t I be?’ ‘Because you do X, Y, and Z?’ And I say, ‘Everything you’re describing right now is Mississippi.’ We are the birthplace of American music; stop playing with me. That’s why I feel like myself and all my other peers around here, we gotta keep doing what we gotta do to keep putting on in a major way.”

Mississippi artists have been getting a lot of attention the past couple of weeks. I just saw Ray Kincaid on Bootleg Kev’s show. I’ve been seeing Akeem Ali a lot. He was actually just on Cam Newton’s podcast. You, Vitamin Cea, Yung Jewelz. Like you said, it’s a lot of talent here. Would you say it’s about time and that everybody is just catching up? 

“ It’s overdue. And I’m so happy because I feel like it’s gonna take all of these different pillars moving at the same time. With myself, Ariel J, Vitamin Cea, with DevMaccc, Coke Bumaye, Akeem Ali, Yung Jewelz, it’s gonna take all of us being great at what we doing at the same time for people to understand—because it don’t have to just be one. And I think we proving that right now. We coming. We got an army.”

Different regions have different styles and sounds in hip-hop. New Orleans has a sound. New York has its sound. Memphis has their sound. How would you define the sound of Mississippi hip-hop? Can ‘SophistiRatchet: RED’ be an example of Mississippi’s sound? A great body of work that encompasses the culture, the slang, the richness and the complexity of this place? 

“ When people wanna know, ‘What does Mississippi sound like?’ It’s Dear Silas. It’s this album right here. It’s ‘SophistiRatchet: RED’ and it’s ‘SophistiRatchet: BLUE.’ That can be the staple. It sounds like what Kincaid doing. It sounds like what Keem doing. It sounds like what Vitamin Cea doing. That’s what it is. And I think people are confused about what the sound is because so many people have come from Mississippi and dispersed across America, and they’ve taken that core sound and then further evolved it into something different.  But it all start here, you know?

Black folk from Mississippi went to Chicago, California, Louisiana. Mm-hmm. This is the birthplace of American music. If you don’t have us doing what we doing—doing rock and roll, blues and jazz—then you don’t get all this stuff. I think we just gotta continue doing it in a major way. … We already know it. We’ll be able to have something to lock onto.”

Dear Silas’ “SophistiRatchet: RED” and “SophistiRatchet: BLUE” albums can be streamed through Apple Music, Spotify, Tidal, and other streaming services. To learn more about Dear Silas, visit dear-silas.com or follow his Instagram page. 

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Jackson, Miss., native Aliyah Veal is a proud alumna of Spelman College, where she earned her bachelor’s degree in English in 2017. Afterward, she attended the Craig Newmark Graduate School of Journalism in New York, gaining a master’s degree in journalism in 2018. After moving back home in 2019, she interned at the Jackson Free Press, covering city council and Jackson neighborhoods before moving up to culture writer. Her interests include tattoos, music and food, really, really good food. She now writes about culture, music and the arts for the Mississippi Free Press.