Reese was discovered by the gospel singer Mahalia Jackson, and her big break came when she won a contest, which gave her a week to sing at Detroit's well-known Flame Show Bar. Reese remained there for eight weeks. Although her roots were in gospel music, she now was being exposed to and influenced by such jazz artists as Ella Fitzgerald, Sarah Vaughan and Billie Holiday. In 1953, she signed a recording contract with Jubilee Records, for which she recorded six albums. Later that year, she also joined the Hawkins Orchestra. Her first recordings for Jubilee were songs such as "In the Still of the Night" (originally published in 1937), "I've Got My Love to Keep Me Warm" and "Time After Time" (1947). The songs were later included on the album "And That Reminds Me" (1959).