At the age of 15, Wilson won a talent contest sponsored by a local television station. The prize was an appearance on a show which she ended up hosting.
In 1956, she joined the Carolyn Club Big Band and toured with them until 1958. In 1960, she released her debut single “Guess Who I Saw Today.” Between March, 1964 and June, 1965 Wilson had four albums in the Top 10 of Billboard’s Top LP’s list. In 1964, she won her first Grammy Award for Best R&B Female Vocal Performance for the album “How Glad I Am.” She later won Grammy Awards for Best Jazz Vocal Album in 2005 for “R.S.V.P. (Rare Songs, Very Personal)” and in 2007 for “Turned to Blue.”
In 1999, Wilson was inducted into the Big Band and Jazz Hall of Fame and in 2004 she was designated a NEA Jazz Master, the highest honor that the United States government bestows upon jazz musicians, by the National Endowment for the Arts. In 2005, Wilson was inducted into the International Civil Rights Walk of Fame.