Some 15-year-olds spend their days in school, their afternoons at the mall, and their nights on the phone with friends. It’s the quintessential teenage schedule — or at least some variation of it, considering technology and the fact that kids don’t go outside like they used to.
Then there are the teenagers who enter their self-discovery phase a little earlier, already knowing what their gift is and wondering how to introduce the world to it. For Maysa, that looked like sitting on the basement floor of her parents’ Baltimore home with a pair of headphones on, asking herself one very big question: How could she get from there to a place where people would actually buy her music and come hear her sing?
Maysa didn’t have the answer yet. But it was only a matter of time before she did, and then some. Four decades later, she has the cosigns, a Grammy nomination and an independent record label to prove it.
After graduating from Morgan State University, Maysa sang background for Stevie Wonder's group Wonderlove before an audition with British jazz-funk band Incognito changed the course of her career. As the voice behind records like "Deep Waters," "Don't You Worry ’Bout a Thing" and "Still a Friend of Mine," her mezzo-soprano — warm and full-bodied like a good Malbec — traveled from Baltimore to stages around the world. Then came her 1995 self-titled debut, the beginning of a solo career that would eventually include 15 albums, a Soul Train Centric Award and Maysa’s Kitchen Karaoke Sundays, the livestream series she launched in 2016 that found an even bigger audience during the pandemic.
And somewhere along the way, the teenager wondering whether anyone would ever pay to hear her sing became a veteran artist thinking about something else entirely: betting on herself. In 2018, Maysa launched Blue Velvet Soul Records, trading the infrastructure and financial backing of an established label for the learning curve of running one herself. The decision gave her something she'd wanted for years: control over her work and a catalog that could build a legacy for her son and future generations. Looking back now, her only regret is that she didn't do it sooner.
On August 16, that journey circles back to Baltimore. Maysa will headline Maysa and Friends at Pier Six Pavilion, returning home to celebrate 35 years in music, right where she first dreamt of making a career out of it. It's a city she says she hasn't had many opportunities to perform in throughout her career, making this homecoming feel a little different. It’s special, it’s personal and she’s hoping everyone comes out to see the gift she’s been perfecting for decades.
In an exclusive conversation ahead of the show, Maysa spoke with Okayplayer about longevity, taking ownership of her career, the music she still loves making and why, after 35 years, the human connection will never fade. And if she has her way, there may even be a Maysa television station somewhere on the horizon.
Okayplayer: You're a Baltimore native who's performed around the world. What does it mean to return home and perform at Pier Six at this stage of your career?
Maysa: Well, it's coming full circle. I mean, I started out in 1991 singing background with Stevie Wonder, and then I got an audition over the phone with the group Incognito. And when I joined Incognito, I just all of a sudden got more education on the Baltimore sound, the Baltimore music and Baltimore musicians. I mean, they'd school me on people that were already at home. So it was a big deal to me that they knew my town even better than I did. And so to have the hit songs like "Deep Waters" and "Don't You Worry ’Bout a Thing" and "Still a Friend of Mine," and then bring them back home to Baltimore and have it so well received, it's a full-circle moment. I've been around the world. I haven't performed a lot in Baltimore throughout my career, but I'm looking forward to this. I was hoping that for this 35, 60, 10 celebration… It's such a big milestone for me. I just hope that people turn out.
What's the biggest lesson you've learned about longevity?
I think just prayer and trust in God have really led my life since I was 15 years old on my parents' basement floor, listening to music with headphones and asking God, "How can I get from here to where people want to buy my music and want to come hear me sing?" To get from there to where I am today, it's just been such an amazing journey. And I'm just grateful that I've been on it this long and hopefully it continues on for a long time. I hope I get one of these Gladys Knight and Pat LaBelle and all those kind of longevity.
What has creative independence allowed you to do throughout your career?
The creative independence, it's just been an amazing choice that I've made in my life because I've been afforded a little bit of creative freedom throughout my career by choosing my music and choosing my images that I've let out into the world, all those things. But to not have to answer to anybody, it's just such an amazing feeling. It's not without the hard work that you have to put into it, but it's worth every minute of it because you can build a legacy for your future family, retirement, whatever you want to do, you can build it, but you have to start. You have to start somewhere. And I'm glad I started in 2018 to build my own record label.
What's one of the most difficult career decisions that you had to make?
That was definitely it. Deciding to create Blue Velvet Soul Records after being with Shanachie Entertainment for 9 years, or nine albums, I should say. And I just thought that from the albums I did with them and maybe the albums previously that I did with other record companies, I didn't think I was going to see any royalties. And if something happened to me, my son and my future grandkids probably would never see any of those royalties. So I decided to take the bull by the horns and take that leap and say, "Look, OK. I got to take this chance. It's a learning curve that's really monstrous." But I did it. I had a great mentor, helped me put my record label together, helped me release the records one by one, singles and then the albums. And so to have that was a big deal.
So taking that leap from going from working for other companies to owning my own company, it was par for the course because I've done things, like I've started a fragrance line. I created my live album. I did a lot to take these leaps. And so that's probably one of the best things I've ever done is take that chance.
What's some advice you would give your younger self, knowing that you later decided to take that leap of faith?
I wish I had done it sooner. I wish I hadn't been afraid to do it sooner than that. I listened to Prince so much. He was saying it so much in the early days. He was like, no, do it yourself, do it yourself. And I heard him, but I was like, how? Because it's so expensive. You go onto radio and [you’re] doing these different things, and promotions and all those things are very expensive things to do. So I was lucky when I started my label. I was working a lot, doing a lot of shows. So I'm self-funded. I've been self-funded.
No investments. I don't have to worry about paying anybody back. So that's the best part of it all. I’m completely… I own everything. And so that's the best part of it all. So getting those checks all to myself, and I don't have to share with anybody, and I don't have to worry about somebody lying to me or if they're paying me and all that kind of stuff. It's a big deal. It's really important.
What is your ritual before hitting the stage and how do you mentally and physically prepare?
I'm going to be honest with you, I'm running until I get on stage. I don't do the things you’re supposed to do. What I try to do when I perform, I know that I have to eat well during that day. So I eat. I don't diet that day. That'd be the only day I don't diet is when I'm on stage. So I have to have food. I tend to make sure that I'm well-rested the night before, and I try not to be stressed out because stress really takes my voice away. It really does. And so I try to do those things. I drink hot tea and honey. And before all that, I'm getting back into my routine where I sip honey, water, and apple cider vinegar.
You put it all in the bottle together and you shake. And it really helps with blood pressure, it helps with any kind of acid reflux you may have. It helps with all that stuff. So it soothes my voice. And so I just tend to do that and sip that during the day when I have a concert.
How do you decide what makes a set list, what gets left out, what changes you might make for a specific city?
Yeah, I think mostly it's hard. Like you said, it's hard because I do have hundreds and hundreds of songs that did well in the last 35 years. And so I try to stick with the ones who are mostly played on the radio. I start there, then I start with whatever single I have out at that time. And then we kind of build it around that. And we try to do what I call, "Go in the vault." And I try to pick out songs I haven't done in a while and I try to bring them back out. It's been difficult. That's probably one of the things that I dread the most is making a set list. It's like trigonometry to me and for some reason I can't take it.
Without giving away too many surprises, can you share anybody that we might be able to expect to see on the stage with you?
I have Avery Sunshine, Jarrod Lawson, Mike Phillips. The comedian Loni Love is my hostess. And a big-time smooth jazz producer Chris “Big Dog” Davis. I have Frank McComb. The Queen of Gospel Energy, her name is Dawn Tallman, and she is fantastic. And I have JJ Sansaverino, a guitarist that's on our smooth jazz circuit right now. He played on my new single, “Street Life,” so I have him there. And the big names that I can't mention are my surprise guests who are going to be fantastic. And people know them, but they're going to be shocked. So I'm happy about that.
Who's your dream collab?
Kem. Yeah, I would love to. I have a song that I really would love him to sing on. I might try to get it to him. I'm not sure. We'll see. I'm going to try.
After everything you've accomplished over the past 35 years in your career, what still excites you the most about music?
Recording and live music. Going on stage, getting ready for my shows, and going into the studio and recording. It's all still amazing. Business-wise, that got old on me. I don't like the business part of the stuff. It's people and some people, the way they treat you, not so nice. But the audiences have been amazing, and the people who buy my music have been amazing. That's why I do Maysa's Kitchen Karaoke Sundays. I've been doing it since 2016. I started way before the pandemic. And then when the pandemic came, it got really, really popular.
I had a lot of big celebrities like Aretha Franklin and Peabo Bryson and everybody listening and watching on Sundays. And so I continued it after everybody else went back to work. I've continued it on. So that's why we're celebrating the 10th anniversary this year. Hopefully soon, I will have my own Maysa television station, so we'll see.
When collaborating, do you prefer working in the studio with the artist rather than emailing or sending the music back and forth?
I know it's cost-effective to do it that way now, but being in the studio and taking pictures afterwards and all that stuff, that's so fun. It's like just bringing that to egg people on and it's a big deal. That's why I tell people, don't worry about AI. AI is just a tool for writing. But for the most part, nobody's going to replace human beings at all.
It's not going to happen. And they can keep trying all they want to, but AI right now is just fun and it's helpful in my opinion. But the live experience will never… The human connection, the spirituality of the human connection will never die.
Maysa and Friends will take over Pier Six Pavilion in Baltimore on August 16. Tickets are available here.
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