She sang avidly from the age of 4, and by the time she was 10 she was the lead singer in the local choir. She had no formal training. “It’s all natural,” she told Jazz Wax.

As a teenager, Ms. Wilson became entranced by the female singers she heard on a local jukebox, especially Dinah Washington, whose ear for irony and keen sense of drama affected her deeply.

“The general humor is a lot of Dinah,” Ms. Wilson said of her style in an interview for the National Endowment for the Arts’ website in 2004. As the inspiration for her glamorous presentation, she cited Lena Horne.

At 15, while she was still a student at West High School in Columbus, Ohio, Ms. Wilson entered a talent contest held by the local television station WTVN; it led to regular appearances twice a week on its show “Skyline Melodies.” Until her graduation, she sang at nightclubs, sometimes with Sir Raleigh Randolph and His Sultans of Swing, an 18-piece band.

Ms. Wilson spent one year at Central State College in Ohio before dropping out to pursue music full time. She honed her skills by touring continuously in the Midwest and Canada with Rusty Bryant’s Carolyn Club Big Band, with which she cut her first recordings, for Dot Records. Seven years passed before she felt ready to move to New York, in 1959.

Ms. Wilson arrived in New York with three goals: to be signed by the influential jazz manager John Levy, who worked with the saxophonist Cannonball Adderley and the British pianist George Shearing; to be signed by Capitol Records, the home of singers like Nat King Cole and Peggy Lee; and to record her first album with the producer David Cavanaugh, who worked with those singers.

Within five months she fulfilled all three goals, even while holding down a day job as a secretary at the New York Institute of Technology. A high-profile gig at the Blue Morocco club led to the contract with Mr. Levy, who got her the label deal, which connected her with Mr. Cavanaugh to produce her debut album in 1960, “Like in Love,” with splashy arrangements by Billy May.