The Academy Awards have shaped film history for decades, often rewarding the best talent while sparking debates over controversial snubs. Understanding who won and who left the ceremony empty-handed helps contextualize cinematic history.
This quiz focuses on specific Oscar milestones, ranging from legendary directors like Alfred Hitchcock to frequent nominees like Peter O’Toole. You will see questions about notable Best Picture winners and performances that define the awards legacy.
After you finish, check out our other quizzes. You can browse general Oscar milestones, see how we rank Hollywood icons, or learn about the history of Golden Age studios.
Which actor holds the record for the most Academy Award nominations for Best Actor without ever winning?
Richard Burton
Richard Burton
Amy Adams
Amy Adams
Glenn Close
Glenn Close
Peter O’Toole
Peter O’Toole
In which 1962 epic did Peter O’Toole receive his first Academy Award nomination for Best Actor?
Goodbye, Mr. Chips
Goodbye, Mr. Chips
Lawrence of Arabia
Lawrence of Arabia
Becket
Becket
The Jazz Singer
The Jazz Singer
Which legendary suspense director famously never won the Academy Award for Best Director?
Steven Spielberg
Steven Spielberg
Martin Scorsese
Martin Scorsese
Clint Eastwood
Clint Eastwood
Alfred Hitchcock
Alfred Hitchcock
Which 1940 film was the only Alfred Hitchcock movie to win the Academy Award for Best Picture?
Rebecca
Rebecca
Vertigo
Vertigo
Rear Window
Rear Window
Psycho
Psycho
What specific honor was Alfred Hitchcock presented with by the Academy in 1968?
The Best Director statue
The Best Director statue
The Irving G. Thalberg Memorial Award
The Irving G. Thalberg Memorial Award
The Academy Honorary Award
The Academy Honorary Award
A Lifetime Achievement Award
A Lifetime Achievement Award
Often cited as one of the least deserving Best Picture winners, which 1952 circus drama beat ‘High Noon’ and ‘The Quiet Man’?
How Green Was My Valley
How Green Was My Valley
The Greatest Show on Earth
The Greatest Show on Earth
Crash
Crash
Around the World in 80 Days
Around the World in 80 Days
Which 1931 Western film is frequently criticized today for its dated portrayal of its central historical subjects?
Gentleman’s Agreement
Gentleman’s Agreement
The Life of Emile Zola
The Life of Emile Zola
Cavalcade
Cavalcade
Cimarron
Cimarron
Which actress holds the record for the longest Academy Award acceptance speech in history?
Greer Garson
Greer Garson
Olivia de Havilland
Olivia de Havilland
Joan Fontaine
Joan Fontaine
Ginger Rogers
Ginger Rogers
Which 1971 film won Best Picture, while ‘A Clockwork Orange’—often considered more culturally significant today—lost?
The French Connection
The French Connection
Fiddler on the Roof
Fiddler on the Roof
A Clockwork Orange
A Clockwork Orange
Cabaret
Cabaret
Which 1998 romantic comedy famously upset ‘Saving Private Ryan’ to win the Academy Award for Best Picture?
The Thin Red Line
The Thin Red Line
Life is Beautiful
Life is Beautiful
Shakespeare in Love
Shakespeare in Love
Saving Private Ryan
Saving Private Ryan
Which film swept the 1985 Academy Awards, often cited as a ‘forgotten’ winner compared to its contemporary nominees?
Out of Africa
Out of Africa
Prizzi’s Honor
Prizzi’s Honor
The Color Purple
The Color Purple
Witness
Witness
In what year was Peter O’Toole first nominated for his role in ‘Becket’?
1965
1965
1955
1955
1970
1970
1960
1960
For which 2006 film did Peter O’Toole receive his final Academy Award nomination?
Venus
Venus
My Favorite Year
My Favorite Year
Lawrence of Arabia
Lawrence of Arabia
The Lion in Winter
The Lion in Winter
For which WWII-era survival drama did Alfred Hitchcock receive a Best Director nomination?
Suspicion
Suspicion
Spellbound
Spellbound
Notorious
Notorious
Lifeboat
Lifeboat
Which 1945 film about alcoholism won Best Picture, leaving Hitchcock’s ‘Spellbound’ empty-handed?
The Lost Weekend
The Lost Weekend
The Bells of St. Mary’s
The Bells of St. Mary’s
Spellbound
Spellbound
Mildred Pierce
Mildred Pierce
Which 1968 musical is often cited as one of the least necessary Best Picture winners, especially considering it beat ‘2001: A Space Odyssey’?
The Greatest Show on Earth
The Greatest Show on Earth
Oliver!
Oliver!
Gigi
Gigi
Around the World in 80 Days
Around the World in 80 Days
In what year was the film ‘Rebecca’ awarded the Academy Award for Best Picture?
1940
1940
1947
1947
1927
1927
1934
1934
For which satire did O’Toole pick up his fifth Best Actor nomination in 1972?
Goodbye, Mr. Chips
Goodbye, Mr. Chips
The Lion in Winter
The Lion in Winter
A Man for All Seasons
A Man for All Seasons
The Ruling Class
The Ruling Class
Which 1941 classic memorably defeated ‘Citizen Kane’ for the Best Picture Academy Award?
How Green Was My Valley
How Green Was My Valley
Citizen Kane
Citizen Kane
The Maltese Falcon
The Maltese Falcon
Sergeant York
Sergeant York
Which 1980 family drama famously beat Martin Scorsese’s ‘Raging Bull’ for Best Picture?
Raging Bull
Raging Bull
Raiders of the Lost Ark
Raiders of the Lost Ark
On Golden Pond
On Golden Pond
Ordinary People
Ordinary People
How many times was Peter O’Toole nominated for the Academy Award for Best Actor throughout his career?
10 nominations
10 nominations
12 nominations
12 nominations
8 nominations
8 nominations
6 nominations
6 nominations
At which Academy Awards ceremony was Alfred Hitchcock given an Honorary Award?
1961 ceremony
1961 ceremony
1947 ceremony
1947 ceremony
1954 ceremony
1954 ceremony
1968 ceremony
1968 ceremony
You can do better
Not bad
Great!
Think you know cinema? If you enjoyed these questions, look at our pages covering war movie history, the craft behind famous directors, and our cult classics collection.
