The Rat Pack and the swagger
The saloon-singer swagger is the easy read. Rat Pack staples and brassy crowd-pleasers like 'Luck Be a Lady' and the up-tempo pop-soul of 'That's Life' are where casual players score before the deeper albums arrive.
Frank Sinatra Quiz: Guess the Song & Test Your Trivia
Test your knowledge of Frank Sinatra's biggest hits, deep cuts and iconic moments.
Top 5 Scores
- #1Sunny_Turtle_28847
- #2Hidden_Echo818
- #3Magic_Badger_18753
- #4Rapid Thunder 23710
- #5Royal_Falcon_17677
Scores are valid for 15 days.
Frank Sinatra at a glance
- Main genre
- Pop (traditional pop and swing standards)
- Real name
- Francis Albert Sinatra, known as Ol' Blue Eyes and the Chairman of the Board
- Best-known songs to guess
- My Way, Fly Me to the Moon, New York New York, Strangers in the Night, Come Fly with Me
- Deep cuts fans miss
- In the Wee Small Hours, Luck Be a Lady, I've Got You Under My Skin, That's Life, The Way You Look Tonight
- Eras in the quiz
- 1940s Columbia crooner, 1950s Capitol swing albums, 1960s Reprise and Rat Pack
- Rat Pack company
- Dean Martin, Sammy Davis Jr., plus duet partners Nancy Sinatra and Count Basie
- Related artists
- Nat King Cole, Ella Fitzgerald, Louis Armstrong
- Quiz difficulty
- Easy on the anthems, hard on the Capitol album cuts and the era-placing rounds
Guess the Frank Sinatra Song
'My Way', 'Fly Me to the Moon' and 'New York, New York' are the anthems players place fastest.
- 01
My Way
- 02
Fly Me to the Moon
- 03
New York New York
- 04
Strangers in the Night
- 05
Come Fly with Me
- 06
In the Wee Small Hours
- 07
Luck Be a Lady
- 08
I've Got You Under My Skin
Frank Sinatra Trivia: The Anthems and the Rat Pack
The French melody behind 'My Way', the Apollo playlist, and the Oscar on the mantel.
- 'My Way' (1969) set Paul Anka's English lyrics to the melody of the French song 'Comme d'habitude'.
- Sinatra's 1964 recording of 'Fly Me to the Moon', arranged by Quincy Jones, was played during NASA's Apollo missions. Quincy Jones's arrangements are a good tell when you guess the artist on a big-band round.
- He won the Academy Award for Best Supporting Actor for the 1953 film 'From Here to Eternity'.
- 'Somethin' Stupid' (1967), a number-one hit, was a duet with his daughter Nancy Sinatra. Duets like this one are ideal when you challenge friends in a multiplayer music quiz.
- 'Theme from New York, New York' came from Martin Scorsese's 1977 film of the same name before becoming his signature closer.
How Well Do You Know Frank Sinatra
The anthems are quick points; the label eras and album cuts settle the match.
'My Way' and the signature anthems
'My Way', 'New York, New York' and 'Strangers in the Night' are the anthems everyone can name. 'My Way' set Paul Anka's English words to the French tune 'Comme d'habitude', a favourite trivia curveball.
The Capitol swing albums
His Capitol run helped popularise the concept album. 'Come Fly with Me' and 'Songs for Swingin' Lovers!' swing hard, while 'In the Wee Small Hours' is a unified album of late-night loneliness, so the mood places the era.
The songs that went to the movies (and the moon)
'Fly Me to the Moon' travelled on the Apollo missions, 'Theme from New York, New York' came from a 1977 film, and Sinatra won an acting Oscar for 'From Here to Eternity'. The screen crossovers trip people up.
About Frank Sinatra
The phrasing and swagger that made him the Chairman of the Board. His anthem 'My Way' borrowed its melody from a French song, 'Comme d'habitude'.
Phrasing is the tell in a Frank Sinatra quiz: the way he leans behind the beat and bends a line is unmistakable. Guess the Frank Sinatra song from 'My Way' and 'Fly Me to the Moon' to 'New York, New York', 'Strangers in the Night' and 'Come Fly with Me', then test your trivia on the Rat Pack, the Capitol swing albums and the saloon ballads. 'My Way' set English words to a French melody, and 'Fly Me to the Moon' rode along on the Apollo missions. Swing and standards like these also anchor a music genre quiz. Find out how well you know Ol' Blue Eyes. Then head to a quiz on music by decade to see how his 1950s stack up against everything after.
Frank Sinatra Quiz FAQ
How does the Frank Sinatra quiz work?
You hear a snippet of a Frank Sinatra recording and name it, then answer trivia across his anthems, the Capitol swing albums, and the Rat Pack years.
Which Frank Sinatra songs are in the quiz?
Signatures like 'My Way', 'Fly Me to the Moon' and 'New York, New York', plus album cuts such as 'In the Wee Small Hours' and 'I've Got You Under My Skin'.
Why is the Frank Sinatra quiz tricky?
He re-recorded many standards across three labels and four decades, so telling the crooner years from the swing albums is where points are won.
Where does the tune for 'My Way' come from?
Paul Anka wrote English lyrics for Sinatra over the melody of the French song 'Comme d'habitude', which is why the anthem has European roots.
Who was Frank Sinatra?
Frank Sinatra, nicknamed Ol' Blue Eyes, was an American singer and actor who led the Rat Pack. He lived from 1915 to 1998.
Is the Frank Sinatra quiz free?
Yes. The Frank Sinatra quiz is free to play on Songtrivia, with no account and no Spotify needed. You can also guess the song with friends in a round.
Sources & methodology
Sources consulted
Wikipedia · AllMusic · Pitchfork · Billboard · Songtrivia editorial team.
Our methodology
Each topic is curated by a Quiz Master with category expertise. Selection crosses cultural impact, chart performance, recognition potential and era variety.