Born in Philadelphia, Thompkins was introduced to music by his father and started singing formally in school. During high school, Thompkins was a member of a local vocal group called the Monarchs who defeated another group called the Percussions in a talent show at Benjamin Franklin High School. Both groups disbanded shortly thereafter. Their remaining members, Thompkins, James Smith, and Airrion Love from The Monarchs, and James Dunn and Herbie Murrell from the Percussions, joined together to form a new group called The Stylistics in 1968.
In 1970, the Stylistics recorded "You're a Big Girl Now", which soon became a regional hit for Sebring Records. The larger Avco Records soon signed the Stylistics, and the single eventually climbed to number seven on the R&B charts in early 1971. Avco approached record producer Thom Bell to work with the group. After the Stylistics auditioned for Bell he was unimpressed, but he ultimately agreed to produce them, because he believed in the potential of Thompkins's soaring high tenor voice. Thom Bell focused the group's sound completely around Thompkins's voice. On most of the group's hits, Bell would have Thompkins sing virtually solo.
From 1971 to 1974, the Stylistics had twelve consecutive U.S. R&B top ten hits and five top ten U.S. pop hits, including "Stop, Look, Listen (To Your Heart)", "You Are Everything", "Betcha by Golly, Wow", "Break Up to Make Up", and "You Make Me Feel Brand New". All of these songs (and everything the group ever recorded) were led by Thompkins, and with the exception of "You're a Big Girl Now", written and composed by Thom Bell and lyricist Linda Creed (1974's "You Make Me Feel Brand New", a No. 2 pop hit, was also sung lead by group member Airrion Love).

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