Drury was born in New York City, the son of James Child Drury and Beatrice Crawford Drury. His father was a New York University professor of marketing. He grew up between New York City and Salem, Oregon, where his mother owned a farm. Drury contracted polio at the age of 10.

He studied drama at New York University and took additional classes at UCLA to complete his degree after he began acting in films at MGM.

On February 7, 1957, Drury married Cristall Othones, and fathered two sons, Timothy and James III. The couple divorced on November 23, 1964 and on April 27, 1968, he married Phyllis Jacqueline Mitchell; the marriage ended in divorce on January 30, 1979. His third marriage was to Carl Ann Head on July 30, 1979; it lasted until her death on August 25, 2019. Drury had three stepchildren from his previous marriages, a stepdaughter, Rhonda Brown, and two stepsons, Frederick Drury and Gary Schero. Drury died from natural causes on April 6, 2020.

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