Plympton was born in Portland, Oregon, the son of Wilda Jean (Jerman) and Donald F. Plympton, and was raised on a farm in nearby Oregon City with five siblings: Sally, Tia, Peggy, David and Peter. From 1964 to 1968, he studied Graphic Design at Portland State University, where he was a member of the film society and worked on the yearbook. In 1968, he transferred to the School of Visual Arts in New York City, where he majored in cartooning. He graduated from SVA in 1969.
Plympton's illustrations and cartoons have been published in The New York Times and the weekly newspaper The Village Voice, as well as in the magazines Vogue, Rolling Stone, Vanity Fair, Penthouse, and National Lampoon. His political cartoon strip Plympton, which began in 1975 in the SoHo Weekly News, eventually was syndicated and appeared in over 20 newspapers.
In 1988, his animated short Your Face was nominated for the Academy Award for Best Animated Short Film. He also became known for other animated short films, including 25 Ways to Quit Smoking (1989) and Enemies (1991), the latter of which was part of the Animania series on MTV, where many of his other shorts were shown.

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