In 1965, Siegel made her recording debut with a group called Young Generation on Red Bird Records. After one single, "The Hideaway", the group disbanded, and then Siegel went on to join the folk trio The Loved Ones (later Laurel Canyon).
In 1972, after the original Manhattan Transfer had disbanded, founder Tim Hauser met Siegel at a party. After recording some demos, she agreed to join the group, and on October 1, 1972, the Manhattan Transfer was reformed. This incarnation of the group has enjoyed international popularity, covering songs from the 1930s through the 1980s in a variety of genres including jazz fusion, R&B, pop, and doo wop. The group has received 10 Grammy Awards during Siegel's ongoing tenure, and was inducted into the Vocal Group Hall of Fame in 2003.
In addition to her work with the Transfer, Siegel has maintained a solo career, releasing her first album, Experiment in White, in 1982.

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