Howland originated the role of Amy in the original Broadway cast of Stephen Sondheim's Company, where she introduced the patter song "Getting Married Today".
Howland was born on May 28, 1939, in Brighton, Massachusetts. At the age of 16, she left home and followed a dancer friend to New York City. After a time of struggling, Howland made her Broadway debut in 1959 as Lady Beth in the musical Once Upon a Mattress, which transferred from off-Broadway. She went on to have roles in the musicals Bye Bye Birdie, High Spirits, Drat! The Cat! and Darling of the Day.
Howland can be seen dancing and singing in the chorus of the movie Li'l Abner (1959) as Clem's wife, alongside future television star Valerie Harper. After appearing in Company, she left New York to relocate to California, where she made guest appearances on television series such as Love, American Style; Cannon; The Mary Tyler Moore Show; Little House on the Prairie; Eight Is Enough; and The Love Boat. For her work on Alice, Howland received four Golden Globe Award nominations. She later took on numerous telefilm roles, including You Can't Take It with You (as Essie) and A Caribbean Mystery.

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