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50 free James Stewart trivia questions with answers — entertainment quiz, new questions added Aug 2026.
James Stewart trivia for classic-film fans, Christmas-movie devotees and anyone who can do the drawl. This quiz follows Jimmy Stewart from the family hardware store in Indiana, Pennsylvania, through Princeton and summer stock with Henry Fonda, to the Frank Capra films that made him a star, Mr. Smith Goes to Washington and It's a Wonderful Life, and the Oscar he won for The Philadelphia Story. It covers the four Hitchcock collaborations, Rope, Rear Window, The Man Who Knew Too Much and Vertigo, the Anthony Mann Westerns that reinvented his career and the profit-sharing deal that changed Hollywood, plus Harvey, Anatomy of a Murder, The Man Who Shot Liberty Valance and his final role voicing a cartoon sheriff. There is also his remarkable second life: rejected as underweight, he flew B-24 combat missions over Germany and retired from the Air Force Reserve as a brigadier general. Questions range from easy to expert, and every answer was checked against a reference page and carries its source. If you enjoy this quiz, try our Alfred Hitchcock, classic Hollywood and It's a Wonderful Life quizzes next.
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Q 01In which Pennsylvania town was James Stewart born in 1908?
Indiana
His father ran the J. M. Stewart and Company Hardware Store and hoped his son would take it over.
Q 02What kind of business did Stewart's father run?
A hardware store
Stewart later gave his Oscar to his father, who displayed it in the shop alongside the family's military medals.
Q 03Which instrument, taken by his father as payment for a debt, became a fixture of James Stewart's life offstage?
Accordion
A local barber taught him to play it.
Q 04What subject did Stewart major in at Princeton?
Architecture
His thesis on an airport terminal design won him a graduate scholarship, which he turned down for summer stock theatre.
Q 05Which future screen legend roomed with a nearly broke Stewart in New York in the early 1930s?
Henry Fonda
They built model aeroplanes together for decades and reportedly came to blows once over politics, then never discussed it again.
Q 06Stewart's breakthrough came in which 1938 Frank Capra film, that year's Best Picture winner?
You Can't Take It with You
He was loaned to Columbia to play opposite Jean Arthur; the film was the year's fifth-biggest hit.
Q 07In Mr. Smith Goes to Washington, Stewart's Jefferson Smith is head of which youth organisation?
The Boy Rangers
The film earned eleven Oscar nominations and was among the first 25 titles chosen for the National Film Registry in 1989.
Q 08Which German-born star played the saloon girl who falls for Stewart's pacifist lawman in Destry Rides Again?
Marlene Dietrich
Stewart's Thomas Jefferson Destry was his last screen role of a busy 1939.
Q 09In The Shop Around the Corner (1940), Stewart and Sullavan play co-workers who unknowingly become what?
Romantic pen-pals
Director Ernst Lubitsch called it the best film of his career; it later inspired You've Got Mail.
Q 10For which film did Stewart win his only competitive Academy Award?
The Philadelphia Story
He played a fast-talking reporter covering Katharine Hepburn's wedding, and beat Henry Fonda, for whom he had voted.
Q 11Who directed the 1940 film that won Stewart his Oscar?
George Cukor
Katharine Hepburn had bought the film rights to the Broadway play, with help from Howard Hughes, to engineer her comeback from 'box office poison'.
Q 12Why was Stewart initially rejected when he tried to join the military in November 1940?
He was underweight
He enlisted successfully in February 1941, months before Pearl Harbor.
Q 13Which bomber did Stewart fly in combat over Europe with the 703d Bomb Squadron?
B-24 Liberator
He was sent to England in November 1943 after more than a year training pilots in New Mexico.
Q 21Which director made 1950s Stewart Westerns like Winchester '73 and The Man from Laramie?
Anthony Mann
Their partnership also produced the biopic The Glenn Miller Story.
Q 22In The Stratton Story (1949) Stewart played a baseball pitcher who lost what in a hunting accident?
A leg
Monty Stratton himself said Stewart 'did a great job of playing me'.
Q 23Which bandleader did Stewart portray in a 1954 biopic co-starring June Allyson?
Glenn Miller
His trombone playing was dubbed; the film won the Oscar for Best Sound Recording.
Q 14Stewart retired from the Air Force Reserve in 1968 holding which rank?
Brigadier general
Promoted in 1959, he became the highest-ranking actor in American military history.
Q 15Which senator initially opposed Stewart's 1957 nomination for promotion to general's rank?
Margaret Chase Smith
The promotion went through in July 1959; he had logged 18 hours as first pilot of a B-52.
Q 16During the Vietnam War, Stewart flew as an observer aboard which aircraft on a 1966 bombing mission?
B-52 Stratofortress
He rarely spoke of his war service, though he discussed the Schweinfurt raid in The World at War.
Q 17What is the name of Stewart's character in It's a Wonderful Life?
George Bailey
The film failed to cover its costs in 1946 and only became a Christmas fixture after its copyright lapsed in the 1970s.
Q 18What eventually turned It's a Wonderful Life from a box-office disappointment into a beloved classic?
Its copyright lapsed, so TV aired it freely
Stewart later testified in Congress against Ted Turner's plan to colourise it.
Q 19In Harvey, Stewart's Elwood P. Dowd has an invisible best friend of what species?
A rabbit
Harvey stands 6 feet 3 and a half inches tall and is described as a pooka from Celtic mythology.
Q 20Stewart agreed to make Winchester '73 (1950) in exchange for what?
Being cast in the film of Harvey
His agent Lew Wasserman then brokered a no-fee, profit-share deal that earned him about 600,000 dollars and helped topple the studio system.
Q 24Stewart made four films with Alfred Hitchcock. Which was the first?
Rope
He played the housemaster whose Nietzschean ideas inspire two students to murder; critics later called him miscast.
Q 25Rope was notable for being Hitchcock's first film in what?
Technicolor
It was also edited to look like a handful of continuous takes, each running up to ten minutes, the camera's film capacity.
Q 26In Rear Window, L. B. Jefferies is confined to a wheelchair in an apartment in which New York neighbourhood?
Greenwich Village
Grace Kelly played his socialite girlfriend Lisa and Raymond Burr the salesman he suspects of murder.
Q 27Which singer co-starred with Stewart in Hitchcock's 1956 remake of The Man Who Knew Too Much?
Doris Day
Hitchcock said the 1934 original was 'the work of a talented amateur and the second was made by a professional'.
Q 28In Vertigo, Stewart plays a retired detective from which city who suffers a crippling fear of heights?
San Francisco
The film pioneered the dolly zoom, still known as 'the Vertigo effect'.
Q 29Which film did Vertigo displace atop the 2012 Sight & Sound critics' poll?
Citizen Kane
On release it drew tepid reviews and poor box office; Hitchcock blamed Stewart for looking too old opposite Kim Novak.
Q 30Which Hitchcock role that Stewart wanted went instead to Cary Grant, after Vertigo's failure?
North by Northwest
Grant was four years older than Stewart but photographed much younger.