Kevin Ross finds love, legacy and warmth ‘This winter’

Kevin Ross has always moved with intention. From his roots in Washington, D.C., shaped by Go-Go culture and Quiet Storm R&B, to building a successful independent career rooted in ownership and authenticity, Ross has never chased trends. He’s trusted his truth.

Now, with “This Winter,” his new collaboration with Rolling Out Music, Ross delivers a timely record centered on love, connection, and emotional recalibration in a world that feels increasingly divided. In this candid conversation, he opens up about his artistic evolution, honoring R&B’s legacy, navigating an AI-driven music landscape, and why human connection remains the most powerful force in music.

For the people who may just be getting to know you, how would you describe Kevin Ross as an artist?

I’m a singer, songwriter, producer, label owner of Our Society Music Group. Father, friend and just an artist advocate overall.

You’re from Washington, D.C. How did growing up there shape your sound and musical ideas?

What I love about D.C. and being from there is Go-Go. So people have an acquired taste as far as the sound. But one thing is for sure is that for Go-Go, when you go into a live performance for Go-Go, there’s only so many bands. And so people continue to see these handful of bands every single week.

And so, it just kind of keeps the live circuit going. So, you get to really hone in on your chops, really understand the art of live performance, how to captivate an audience, but then also to keep a revolving door as well.

So, that’s one thing that I learned. And then also the entrepreneurial spirit of the city, having different types of clothing brands that we rocked and supported, that we paid good money for.

And just the flavor and the flair that we had of our own. So, D.C., love it. Always.

A lot of artists spend years trying to find their sound. When did you realize you already knew who you were musically?

To be honest, I knew who I was musically early on. I just second-guessed myself once I got into the music industry because I felt like everybody else knew better than me about me. And then, you know, sometimes you got to go full circle to say, man, the sound that I was creating early on was spot on. And sometimes you need time to develop, to mature, to grow up, to have the business acumen in order to understand how to market, to put out that sound as well.

And so, I think everything took time. So, I would say I knew early on, had to go on a whole exploration and journey of trying different things out and expanding my palate to get back to what I truly love.

How do you incorporate your musical influences into your music?

A lot of people would just think that D.C. is Go-Go. But one thing that we take pride in is that there’s a radio station called WHUR, which is Washington Howard University’s radio.

And so, this is a place where they created the format called Quiet Storm, what we know now as adult R&B. And so, as I was growing up, I was listening to the Smokey Robinsons and the Donny Hathaways and all of these amazing artists that would come on to Quiet Storm.

And so, I wanted to pay a tribute and homage to WHUR. And that’s kind of where my sound leans towards. It’s more of the Stevie Wonder-esque, more the lush chords, kind of jazz-like, in a way. And so, that’s kind of where I live.

You’ve built a successful career while staying independent and launching your own label. Why was owning your artistry so important?

Owning my artistry was not necessarily the mission at first. It was about exposure. It was about making sure that my face was seen and that the music was heard. Initially, I was signed to a major label at first and had to go through that system. And I wouldn’t change that because I learned so many valuable lessons about being in a major label system.

But it also gave me a greater appreciation when I went out on my own to understand the tactics and the means of getting your music and IP out there. And so for me, now, being more successful as an indie than I ever was as a major is a true testament to patience, having a little bit of finances as well, being able to scale, making sure that you have a team around you, and making sure that you have mentors and just great people to give you advice.

But then also to be able to listen to that advice, to know what to take, and then also to take as a grain of salt as well. And so, for me, it’s a journey. And so, at this point in my life, I felt like I’ve kind of checked most of the boxes that I’ve aspired to be, as a child. And so, now everything that I do is a demonstration, and it’s a demonstration of what can be, what is possible for the next person.

So, it’s not about my glory anymore or self-vanity of saying, great job, K. But it is a demonstration to let the next generation know what is possible.

What does connecting to an audience mean to you?

Connecting is everything, especially nowadays when you’ve got AI artists running it up as far as on streaming, and they can make just as good a music as you can, and people can’t tell. And you can’t be mad at that because it’s a reflection of the time as well.

If we spend half of our time on a synthetic phone, then sometimes we can get synthetic emotions as well. And so, I’m guilty of that as well. Sometimes I listen to these AI artists and I’m like, ‘Dang, that sounds great.’ Yeah. I mean, like, I’m looking at the artists and it’s like, it’s AI.

And so, one thing that AI can’t do right now is the fact that they can’t touch the people physically. They can’t do these type of interviews. They can’t look you in your eye and understand your story, or at least try to understand, to empathize with you.

And so, for me, that is the superpower of every real artist that’s out there, is to go out into the streets or on stages, performances, and shake people’s hands and say, I really appreciate you coming out.

Because it’s beyond just coming out and sitting there selling out. It’s about somebody actually woke up with the intention of going to see you, buying the ticket, getting dressed, taking a shower, going into their car, stupid parking lot, and all that stuff, waiting in line to then sit down to see you perform for all of an hour.

And so for every artist, we can’t take that for granted. That is the connectivity. That is the human experience personified. And so I can’t take that for granted.

What’s one thing about your music or message you’ve refused to compromise no matter how the industry shifts?

This is what somebody told me a long time ago: The truth don’t change with trend. So, your truth, your authenticity, your story, your narrative, that is all connected to you. You can try to do everything under the sun, but people can tell what’s real and what’s not coming from you. It may sound good. It may be a smash. But it may not be a smash on you.

And so, that’s the bottom line, is what is believable? What is oozing out of your spirit to say when people hear that song or see that video, they say, “I believe them.” That’s the most important thing about this whole process. Is it believable? Is it something that people can carry with them? And are you the right [messenger] or vessel to carry that?

So be true to you.

From The Awakening to Drive to where you are now, how do you feel you’ve evolved as an artist?

In every sense as far as growth is concerned, like by leaps and bounds. Because when I was doing The Awakening, it was a lot of cooks in the kitchen. And everybody had a vision of what I could be, what I should be. And so, sometimes when you get that type of pressure on you, the product is a little murky at times. Sometimes artists get lucky, and that first album is just crazy because they got the right chefs cooking up this gumbo. That wasn’t the case for me.

And so, what it taught me is, you know what, sometimes it’s great to have your — I wouldn’t say mistakes — but your early beginnings, your humble beginnings, on display.

Because it allows for people to have this track record to say, this is where you started. This is where they are now. And so, even for me, sometimes I can reflect back on those records to be like, wow, how much I’ve grown vocally, musically, lyrically, song-structure-wise.

Knowing what radio wants when I’m trying to deliver a radio record. Knowing what fans want as far as DSPs. And, certain songs belong in certain areas. Like, you just can’t put all of your babies on one project and think that all of them are going to go. So everything needs a certain home inside that. And then business acumen as well.

I was kind of forced into understanding how to make the music work in a marketplace. It’s deeper than just making a great song and then just putting it out and crossing your fingers and hoping that it goes. Like, nah. There’s a lot behind the curtain that a lot of people don’t understand. And there’s a lot of strategy and intention behind each and every artist and their music.

Your music consistently leans into vulnerability and emotional intelligence. Was that always natural for you, or something you grew into over time?

No, that was always natural. That was innate, to be honest. I’ve always been an old soul, like 17 years old, making old-man music. And so, I think it was just something that God decided to bless me with. He knew that I was going to be able to articulate these messages in a very interesting way. And so I’m grateful for that. That’s a gift and a curse, though, for sure.

You’re known for honoring R&B legacies while still pushing the genre forward. Why is that balance important to you?

I think that now it’s so important to — I think it sounds raised. My mom, my pop, my grandmother. And so I was around just that, being a bridge, being like what J. Cole would say, like the middle child. You got the old heads over here, and you got my younger brother and cousins, and I’m just kind of right there in the middle.

You have these musical debates, and who’s better, what type of artist y’all listening to, and it’s nothing like what we used to listen to, this, this, and that.

And so I took all of this information and I said, “Okay, well, how can I make music that my mom and my dad could be proud of, but also that my younger cousins and brother can bop to?” And that can be hard at times, like trying to satisfy both audiences. And you get a lot of hits and misses.

But it’s about being intentional every time that I go into the studio to say, “Okay, my brother wants something that knocks, but my mom wants something that’s clean enough and honest enough that she still sees her son inside of that.” And so that’s kind of the line that I see that I teeter.

At this stage in your career, why does “This Winter” feel like the right record for you?

“This Winter” is the right record for me right now because of the messaging of it. As crazy as the world is right now, the divisive messages that we hear on a daily basis, we needed a song that just says, “Look, it’s a lot going on right now, and all I need is love.”

Whether that’s love for family, whether that’s love for a significant other. And so I felt like it was really timely. And I can’t take credit for it, honestly. Shout out to Munson. Shout out to Xavier. Shout out to Pyro and everybody that’s involved over at Rolling Out Music as far as making this record happen.

And I’m blessed to be a collaborator. I think there’s nothing greater than having someone that can say, okay, I can do 100 percent of a record, but someone can place an idea in front of me to say, how does this fit for me? How can I create this message to make it believable?

And so I think this was a great collaboration. So shout outs to everybody that’s involved because I feel like it’s timely.

And we’re Top 20 at radio within two weeks. So it’s amazing.

What was your initial reaction when you first heard “This Winter”?

Well, my first initial reaction was different because it was named a different record. And so, we had a conversation as far as how we can make this record a little bigger, a little more to the masses. And so, we agreed. And honestly, we sat on the record for about two years.

It’s all about divine alignment and timing. I never question God’s timing. So when I got the call like, “Yo, you remember this record?” I had to listen to it again. And of course, after two years you want to do revisions or different vocal stuff, but it really, really came together. And like I said, Munson was truly the mastermind behind it in a sense of bringing everybody together, putting the pieces together. And so, yeah, super duper grateful.

What was your process for stepping into someone else’s writing and making it feel personal?

Honestly, you got to know who you are first. So, when you’re reading something, you’re trying to figure out how it connects with you first and foremost. But if you don’t know who you are, then you wouldn’t know how to connect. And so, for me, as I was listening to the record, I’m like, okay, this is what I resonate with. This is where I can curtail it and change it. And so, like I said, just amazing penmanship and laying down a blueprint as far as Munson and Xavier. And they made it easy for me to contribute and to add my own little thing to it.

Because sometimes when you collaborate, you bump heads. But they really opened up the door and made it feel like home as it pertains to bringing me into the creative fold.

At what point did it stop feeling like someone else’s story and start feeling like yours?

I think as soon as I recorded it. Once I recorded it, and I felt my voice inside of it. And then listening back, I was like, “Okay, I believe it.” And yeah, like I said, two years later, I listen back and I’m like, “Okay, it still feels true for me.” And I just stay true to that. I don’t try to second-guess it or overthink a situation. If it feels good, if it sounds good, and it’s believable to me, I’m going to go with it.

How do you balance honoring the writer’s original intent while still bringing your own emotion and perspective to the song?

Respect and reverence is definitely how I make sure that I keep the integrity of a song, of a writer, or a creator that has presented something. I always want to make sure that I’m doing it justice and making them proud because I understand what that feels like. Being a writer myself, to have a song and you’re like, “Okay, I have this person in mind, and I hope that they sound exactly the way that I envisioned them to sound.”

So, I know what that feels like as a writer. And so for me to be on the other side as an artist, of course I want to deliver for the writer. Of course, I want to make sure that they can feel each and every lyric that they’ve put out there. Because to see that smile on their face, it’s like, okay, we got one person. Can we get you to many more? So, that’s the magic of it. That’s the alchemy of music.

Winter can symbolize healing, isolation, reflection, or survival. What does winter represent to you in “This Winter”?

For me, it’s recalibration. It allows for me to look at where I’ve been within the year and kind of reflect because things move a little bit slower. It may not completely stop, but it slows down enough for me to say, “Okay, what could I do different? What did I love?” Spend time with family and then really gear up for next year. You know what I mean? So, that’s kind of been my tradition for a while. It’s just like make the assessment, plan it out, recalibrate, and then go at it. I think that works for me.

I can’t do the whole nonstop go, go, go. When winter hits, it’s like, nope, slow down, shut it down for a little bit, and yeah, see me when the sun comes out a little bit.

What does performing This Winter demand from you emotionally on stage?

It just demands honesty and preparation as well. It’s important to prepare for those moments so that people can feel what you’re saying and bring it to life.

What does preparation look like for you as an artist?

Preparation for me in performance looks like warming up for about 30 minutes. I’ll go on the treadmill. I run a mile just to kind of get my wind up and get the blood flowing. Prayer. I got two songs that I use as far as vocal warmup to kind of like the icing on the cake — Joni Mitchell’s “Help Me” and “Climax” by Usher. And then I’ll be ready to go as long as my vocal is warm, I’m in a good space, and that blood is flowing through. I’ll be all right.

What do you think listeners will feel the most when they hear “This Winter” for the first time?

Well, when you hear “This Winter” for the first time, you should feel warm and fuzzy inside. You should feel the love that it took in order to create the record and take whatever you need from it. At the end of the day, music is subjective. It’s to be interpreted in whatever way that you see fit. As long as people are listening, that’s what matters most.

Who do you feel this song is really speaking to right now?

I feel like “This Winter” is speaking to an audience that is in need of love. That’s in need of connection. It spoke to me. And so, I think there’s a large audience out there that’s in need of this record, whether we’ve reached them yet or not. That’s the beauty of music. Music lives on forever. It’s a part of the catalog.

Whether you discover it this year or 10 years from now, it should feel just the same when you discover it. So that’s the magic of it.

How does it feel collaborating with Rolling Out Music in a way that’s rooted in storytelling and creative trust?

Yeah. Shout out to Rolling Out Music and this collaboration. Storytelling is everything. The narrative is everything. But most importantly, two Black entities coming together cohesively, in harmony, to do something that is not only productive musically but also philanthropically.

In the sense of going to different radio stations, doing giveaways, giving away phones, people’s reactions, and a sense of saying, I don’t have much to give this Christmas, or to give to my family this Christmas, but you giving into us, someone inside of us, it means so much. Thank you.

And to some of us, it’s like it’s just a phone. But to somebody else, it can be everything that they need. It could be a confirmation from God to them to keep going or to connect more with their family. And so I think it’s a beautiful thing that Rolling Out Music is doing. And I’m glad to be a part of it for this holiday season.

So, I’m looking forward to seeing what Rolling Out Music will do in 2026 and then on, and possibly collaborating in the near future.

Why does “This Winter” feel especially relevant in this cultural and emotional moment?

“This Winter” feels important to the culture right now because we don’t have a lot of original holiday music, as much as we did maybe 15 to 20 years ago. I think a lot of people just do covers. They’re like, I got my version of “Santa Baby.” I got my version of “Let It Snow.”

And that’s fine. However, we are creative enough, I believe, in this generation to make our own classics. It’s just the fact of who’s daring enough to do that? I feel like we are more sensitive than what we realize as it pertains to a collective. So, what we see and how we feel resonates in a different way.

We see it on film. We see it everywhere else. And it needs to reflect the music in the same way, especially during the holiday season. And so, I felt like it was imperative for this message and “This Winter” to get out there. I feel like hopefully this will be a drop in the bucket, or at least raise some type of flag or alert or alarm to a lot of artists to say, “Hey, it’s okay to make original music, and it can work.”

When people look back on this era of your career, what do you hope “This Winter” represents?

Damn, he was working hard. Yeah. Yeah. He was on it.I mean, I’m coming off the heels of a No. 1 record with “Love in the Middle.” And so literally three months later, I’m back at radio. Like I say, within two weeks, being in the top 10 is a true testament to the relationships that we built, the quality of the song, the intention, the energy. Like I said, it’s just a collective thing that you can never really calculate.

You can plan for it, but it’s kind of like meeting God halfway and being like, “This is my best. This is what I have to present. Take it from here.”

And so for me, that’s where I sit in this whole thing. So, it’s been amazing. And I want people to think like, “You know, he was really working out here. He added with ‘Love in the Middle,’ and then we got ‘This Winter,’ and they both feel great.” And hopefully it’ll be a part of the catalog.

What would you like to tell your fans or anyone hearing your music for the first time about “This Winter” and about yourself as an artist?

Well, if this is a message for anybody that is listening to me for the first time, thank you so much for taking the time out to discover me. I’m here to be discovered. I call myself a discovery artist. And if you fit inside of this box, I make music for what I would like to call the blue-collar love. That means nurses, teachers, doctors, anyone that gets up from a nine-to-five. That’s not exclusive to entrepreneurs and stuff like that. However, I feel like I resonate more with the working class.

All that to say is that I’m grateful, and I’m appreciative of your ears, your heart, and your attention. Please take what you need from “This Winter” — the message, the vibe, the melody, the music. God bless you. Happy holidays and all of that good stuff.

Cover Photography by Javi Hvbris