- In the early 1950s, Whitmore conducted an acting workshop in Hollywood; one of his pupils was a struggling young actor, then unknown, James Dean. Whitmore helped Dean get some jobs in Los Angeles but encouraged Dean to go to New York to audition for the Actors Studio. Dean was one of the few accepted the year he auditioned.
- Served in the United States Marine Corps during World War II, attaining the rank of Second Lieutenant, serving in Panama and the Canal Zone.
- Remains the only actor ever nominated for an Academy Award for a one man show for Give 'em Hell, Harry! (1975).
- He appeared in The Twilight Zone (1959) while his son James Whitmore Jr. (born James Allen III) appeared in The Twilight Zone (1985).
- Performed his one-man stage show on and off for thirty years (1970-2000). He had nearly eight hours of various comments about the topics of the day memorized, changing the show each time he performed it. His costume is now housed at the Smithsonian Institute.
- Earned a football scholarship at Yale University though extensive knee injuries led him to give up the sport.
- He is survived by eight grandchildren, including James Whitmore III (born James Allen IV).
- Has twice played a character who was incarcerated but didn't want to go home for fear of change. In On Thursday We Leave for Home (1963), he was marooned on a planet and was the only colonist who wanted to stay because going back to Earth would mean he would lose his authority. In The Shawshank Redemption (1994), he didn't want to be released from prison.
- Attended Choate Rosemary Hall in Wallingford, Connecticut on a football scholarship. Was a pre-law collegiate at Yale University but quit playing football after suffering two knee injuries. While at Yale, he set up the campus radio station and starred in a nightly sports news show called "Jim Whitmore Speaks".
- Appeared at the Peterborough Players Theater in Peterborough, New Hampshire in the play "Tuesdays With Morrie" with his son, James Whitmore Jr.. (June 2006)
- Reprised his role as the Stage Manager in "Our Town" at the Peterborough Players in Peterborough, New Hampshire. (August 2008)
- Years after losing the Academy Award for Best Supporting Actor to Dean Jagger in Twelve O'Clock High (1949), he appeared twice on the television series based on that film: 12 O'Clock High (1964).
- Well known for his role as Captain Benteen in On Thursday We Leave for Home (1963), considered by many fans to be the best hour-long entry in the series' history.
- Is a member of Yale University's exclusive Skull & Bones club, an undergraduate secret society famous for the post-graduation accomplishments of its members. Other living members include President George W. Bush and his father, former President George Bush, Senator John Kerry and Pulitzer-Prize winning historian David McCullough. Deceased members include President William Howard Taft, political commentator William F. Buckley and President Bush's own grandfather, Prescott Bush, a U.S. Senator and partner in the Wall Street white shoe brokerage firm of Brown Bros., Harriman.
- He was awarded a Star on the Hollywood Walk of Fame at 6611 Hollywood Boulevard in Hollywood, California on February 8, 1960.
- Met and married first wife Nancy Mygatt while studying at the American Theatre Wing. She was their press agent at the time.
- Whitmore (the youngest of four children)'s father was the Executive Secretary for the White Plains, New York Park Commission.
- He appeared in two films nominated for Best Picture Oscar: Battleground (1949) and The Shawshank Redemption (1994).
- First job in the entertainment field was as a radio director for the Yale University station.
- He was a lifelong Democrat.
- He appeared with Keenan Wynn in five films: Angels in the Outfield (1951), It's a Big Country: An American Anthology (1951), Kiss Me Kate (1953), All the Brothers Were Valiant (1953) and The Deep Six (1958).
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