Instructions: Answer each question to the best of your ability. Once you select an answer, you will then find out if it is correct or not. There will also be an explanation to help you learn more about history. An orange “Continue” button will appear and allow you to move to the next question.
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Which of the following nicknames was commonly attached to Sinatra on account of his handsome appearance?
"Ol' Blue Eyes"
"Mr. Dapper"
"The Head-Turning Mr. Sinatra"
"Angel Face"
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Which of the following cities is Sinatra's hometown?
Albany, New York
Los Angeles, California
Hoboken, New Jersey
New York, New York
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What is the name of the group of enthusiastic young women who in the 1940s would passionately show support for Sinatra in all of his endeavors?
The Rockettes
The Fourth Army
Bobby Soxers
Glendale Gals
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What 1946 album was the debut solo album by Frank Sinatra?
The New Music of Frank Sinatra
Melodies from Frank Sinatra
The Voice of Frank Sinatra
Frank Sinatra Sings!
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What Frank Sinatra song features the legendary lyrics, "You're riding high in April, shot down in May"?
"London Bridge"
"That's Life"
"Brazil"
"Love with Me"
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In 1960, Sinatra founded which of the following record labels with which he would release most of his subsequent works?
Apple Records
Reprise Records
Soundboard Records
Hoboken Sounds
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What is the name of the legendary 1953 war drama film which Sinatra's performance in won him an Academy Award for Best Supporting Actor?
From Here to Eternity
Heartbreak Ridge
Swansong
Days of Memory
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What is the name of the song which Frank Sinatra wrote and performed as the theme for the Martin Scorsese movie New York, New York?
"The Concrete Jungle"
"Friends in Manhattan"
"The Big Apple Blues"
"New York, New York"
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What American President awarded Sinatra the Presidential Medal of Freedom?
Ronald Reagan
Gerald Ford
Bill Clinton
George W. Bush
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Sinatra's 1968 album Francis A. and Edward K. was a collaboration between him and what other notable artist?
Ella Fitzgerald
Louis Armstrong
Elvis Presley
Duke Ellington
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What Frank Sinatra song features the lyrics, "Let me see what Spring is like on Jupiter and Mars"?
"You and Me In Eternity"
"Stars Above"
"Fly Me to the Moon"
"Days in Night"
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What is the name of the supergroup that Sinatra formed with other contemporaries such as Sammy Davis Jr. and Dean Martin?
The Rat Pack
The Boston Willpowers
The Peacekeepers
Live and Love
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Sinatra performed a lauded role in what 1962 political thriller about Communist brainwashing of American soldiers?
Live and Learn
The Maltese Falcon
The Manchurian Candidate
Habeus Corpus
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To this day, Sinatra has sold around how many records?
50 Million
75 Million
120 Million
Over 150 million
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What Frank Sinatra song features the famous lyrics, "But what is a man if not himself"?
"Reflections"
"My Way"
"At the End"
"Opportunities"
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Also, be sure to try our Legendary Albums of the 1950s Quiz.
Writer / Quiz Creator
Andrew Nicholas is a passionate reader and writer on the subjects of history and mankind. He is a published author, critic, and poet who grew up in the friendly scenery of rural Ohio. He is a graduate of Wright State University and a regular student of historical curiosities.