[2][3] Pierson was born in Chappaqua, New York, the son of Louise (née Randall), a writer, and Harold C.

[1] Pierson's family was the subject of his mother's 1943 autobiography Roughly Speaking and a 1945 movie of the same name, starring Rosalind Russell and Jack Carson as his parents.

He got his break in Hollywood in 1958 as script editor for Have Gun – Will Travel and moved on to write for the television series Naked City, Route 66 and others.

He wrote or co-wrote several successful films, including Cat Ballou and Cool Hand Luke, which were both nominated for Academy Awards.

He directed and contributed to the screenplay of the 1976 remake of A Star Is Born; and the in-fighting between himself, Barbra Streisand, Kris Kristofferson and producer (and at the time boyfriend of Streisand) Jon Peters on the film led him to write the article "My Battles with Barbra and Jon" for The Village Voice.