Maysa Leak: Baltimore Roots, Artistic Independence, and Speaking Truth

Maysa Leak (born August 16, 1966) is an American jazz singer and songwriter, celebrated for her versatile vocal style combining jazz, R&B, and soul influences. After graduating from Milford Mill High School and Morgan State University in Baltimore, Maysa launched her professional career performing with Stevie Wonder’s Wonderlove, later gaining international fame as the lead vocalist for Incognito. Through decades of solo and collaborative releases, she has remained a beloved figure in smooth jazz communities, continuing to live and create in her hometown of Baltimore.

Baltimore’s Lasting Influence

“My mother took me to see Purlie when I was six years old at the Morris Mechanic Theater. Melba Moore came out on stage, and the lights came up. I saw the costumes, the music, her singing, and the dancing. I was just six years old, but I knew I wanted to do that. I wanted to make people feel the way she made me feel. And that’s why I wanted to be in music. Baltimore has always surrounded me. This is my hometown.”

Baltimore offered Maysa formative opportunities, from high school music programs to jazz clubs like the Jazz Closet, where she learned to front bands and connect authentically with audiences. Mentors including her uncle Caleb (who introduced her to jazz via PBS and Al Jarreau) and veteran performers like Anita Green taught her the importance of musicianship and honest self-expression. Collaborations with local giants—Gary and Greg Granger, Gary Thomas, Dontae Winslow—further grounded her in the city’s musical legacy, enabling her to emerge as both a local talent and an international star after returning with hits like “Deep Waters.”

Owning Her Artistic Destiny

“After doing nine records for them, it was like I was just at the same place. And I didn’t think they were supporting me. So I might as well just start myself and do.”

Frustrated with traditional record labels that failed to advance her career despite her multiple albums, Maysa decided to take control by launching her own label. Owning her masters and building a business legacy for her son and future generations became personal motivators. “Owning my own self was something—of course I’ve heard Prince and other artists say this is so important, owning your masters—but I thought this was the time, that I was around 50 years old.”

The transition, however, came with obstacles: funding every project personally through live performances, handling every aspect of operations from marketing to administration, and balancing entrepreneurial demands with creative output. Nevertheless, Maysa describes ownership as empowering and necessary for long-term artistic autonomy.

The Cost of Speaking Out

Maysa’s desire to speak openly on social and political matters is complicated by concerns for her family’s safety and the pressures of public visibility. Maysa expresses hesitation about posing candid political views online, fearing targeted backlash in today’s climate where artists and their loved ones may become targets for their advocacy. “I really don’t care if people say, ‘Oh, I’m not going to listen to your music anymore.’ That doesn’t bother me,” she says, but adds. “I figured if I say anything, people go after you. They don’t care anymore. They’re so evil that they go after everything.”

Although she’s written music addressing togetherness and change (“You Are Not Alone,” “Can We Change the World”), she admits feeling blocked creatively due to the sadness she feels about the state of the world—balancing the urge to share her truth with the instinct to protect those closest to her.

Maysa’s life and music remain inextricably linked with Baltimore’s creative spirit and resilient community, exemplifying both the rewards and challenges of pursuing artistic integrity in a complex world.

–by Charmaine Michelle

Charmaine Michelle is a trumpet player, band leader and digital strategist who owns Allegiance Branding a digital marketing firm. She moved to Baltimore in 2010 after receiving the Noble Jolley Sr Jazz Scholarship to attend Peabody Conservatory. She has her own jazz EP released in 2017 called “Love Takes Time.”