With the Impressions, Mayfield produced, wrote, and sang lead on numerous hits some included uplifting civil-rights-movement messages. Mayfield then entered a prolific period during which his writing and singing would come to define the Chicago sound, which rivaled Motown in the early and mid-'60s. A re-formed Impressions with Mayfield, Gooden, and Fred Cash signed with ABC-Paramount and scored with Mayfield's flamenco-styled "Gypsy Woman" (Number 20 pop, Number Two R&B). Mayfield and Butler teamed up again in 1960, with Butler singing and Mayfield writing and playing guitar on "He Will Break Your Heart" (Number Seven pop, Number One R&B). Butler's cool baritone dominated the record, and he left to pursue a solo career. In 1958 they, along with Sam Gooden and Richard and Arthur Brooks, recorded "For Your Precious Love" on Vee-Jay Records.
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He met lifelong friend and collaborator Jerry Butler at a gospel function, and they went on to form the Impressions, a rhythm & blues vocal group, in 1957. Mayfield began singing with gospel groups such as the Northern Jubilee Singers, who were part of his grandmother's Traveling Soul Spiritualist Church.
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Curtis Mayfield was a driving force in black music from the early '60s through the mid-'70s, as a singer, writer, producer, and label owner.