Sherry graduated from the Acting Conservatory of SUNY at Purchase in 1989 with a Bachelor of Fine Arts. She got her first role on the soap opera Guiding Light, playing Christina "Blake" Thorpe from 1989 until 1992. After three years she left the show, but soon returned to the small screen on the ABC drama NYPD Blue playing Manhattan A.D.A. Laura Kelly, the ex-wife of officer John Kelly (David Caruso) during the first season (1993-94) of the series. Unsatisfied, she was released early from her contract.

With minimal delay she became one of the original cast members of ER. Her personal success mirrored the show's success; she was nominated for an Emmy Award for lead actress during each of her first three seasons of the show. However, despite being contractually tied to ER for five seasons, a desire for a "normal life" prompted her to leave the successful prime-time drama early in its third season. In order to be released from her contract Stringfield was forced to sign a no-work agreement, which blocked her from working on television for the remainder of her original contract.

After leaving she married Larry Joseph, taught at her alma mater, had a baby, and took roles in films such as 54 and Autumn in New York. After a few years she approached the producers of ER and then rejoined the cast in 2001, the show's eighth season. In August, 2005, however, she announced that she would be leaving the show again as the 12th season came underway. Sherry's next project is a role in the upcoming film Gone, scheduled for release sometime in 2006.