Upon graduating, Maysa moved to North Hollywood to perform with Wonderlove on the Jungle Fever soundtrack and appeared in live and televised performances to promote the film. To pay her rent, Maysa also recorded jingles on her days off from performing with Wonderlove and worked at local record shops. In 1991, she was recommended to the British funk-jazz group Incognito by producer Steve Harvey, a mutual friend of Maysa's and of the band's leader, Jean-Paul "Bluey" Maunick.
Maysa moved to London and joined the band in time to record the 1992 album Scribes, Tribes & Vibes, which included the hit single "Don't You Worry 'Bout a Thing." She also recorded the 1993 album Positivity with Incognito before returning to Baltimore in 1994 to record her first solo album, Maysa. "What About Our Love," the album's single, reached number 52 on Billboard's Hot 100. In 1997, Maysa returned to Incognito and recorded Beneath the Surface. During this time she began collaborating with the neo-blues group Grainger, and appeared on their album Phase 1; she also recorded with Rick Braun, Rachel Z, Rhythm Logic, and Pieces of a Dream. Incognito's No Time Like the Future followed in 1999.
Throughout the 2000s and early 2010s, Maysa was remarkably productive as a solo artist and continued to be appreciated more in the U.K. than in the U.S. The varied All My Life (2000), Out of the Blue (2002), and Smooth Sailing (2004) featured an array of sophisticated R&B, lush deep house, and crossover jazz, as well as covers of songs originally recorded by Sly & the Family Stone, Gil Scott-Heron, and Earth, Wind & Fire. In 2006, she began a lengthy association with the Shanachie label. Sweet Classic Soul (2006) and Feel the Fire (2007) were highlighted by reinterpretations of the Stylistics, Luther Vandross, Commodores, and Evelyn King, while Metamorphosis (2008), A Woman in Love (2010), and Motions of Love (2011) were dominated by new songs written by and with the likes of longtime associate Rex Rideout, Will Downing, Ledisi, and Chris Davis. Maysa considered Blue Velvet Soul (2013), her tenth solo album, to be her best work. ~ Heather Phares & Andy Kellman, Rovi