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Quizzes > Music

Frank Sinatra quiz: How Well Do You Know Ol' Blue Eyes?

Quick, free Frank Sinatra trivia quiz to test your knowledge. Instant results.

Editorial: Review CompletedCreated By: Lukas MarconiUpdated Aug 27, 2025
Difficulty: Moderate
2-5mins
Learning OutcomesCheat Sheet
Paper art collage of fedora microphone and musical notes for Frank Sinatra trivia quiz on dark blue background

This Frank Sinatra quiz helps you test what you know about his classic songs, film roles, and onstage moments. See your score in minutes and pick up a fact or two as you go. When you are done, try our singer quiz, tackle a music knowledge test, or switch eras with The Weeknd quiz.

In which city was Frank Sinatra born?
Hoboken, New Jersey
Hoboken, Alabama
New York City, New York
Newark, New Jersey
Frank Sinatra was born on December 12, 1915, in Hoboken, New Jersey, where his parents lived in a small apartment. He spent his early years there before the family moved to other parts of New Jersey. Hoboken's musical environment in the early 20th century provided a backdrop to his childhood influences.
What was Frank Sinatra's middle name?
Anthony
Arthur
Andrew
Albert
Frank Sinatra's full birth name was Francis Albert Sinatra. His middle name, Albert, honors his father, Anthony Martin Sinatra, and reflects his Italian heritage. This name appears on all official records and biographies.
Which nickname was Frank Sinatra famously known by?
The Voice of an Angel
King of Swing
Mr. Cool
Ol' Blue Eyes
Sinatra was widely known as "Ol' Blue Eyes," a reference to his striking eye color and charismatic persona. The nickname became synonymous with his image as a suave and sophisticated crooner. Fans and media alike used this affectionate moniker throughout his career.
With which big band leader did Sinatra gain his first major success?
Benny Goodman
Tommy Dorsey
Glenn Miller
Artie Shaw
Frank Sinatra joined Tommy Dorsey's orchestra in 1940, which catapulted him to national fame. His smooth phrasing and nickname were nurtured under Dorsey's direction. The band's hit "I'll Never Smile Again" marked Sinatra's first chart success.
Which song is often considered Frank Sinatra's signature tune?
My Way
Strangers in the Night
Come Fly with Me
New York, New York
"My Way" became synonymous with Sinatra's persona of self-assurance and reflection. Released in 1969, it topped charts worldwide and remains his most enduring recording. The song's lyrics about life choices resonate deeply with audiences.
In which decade did Frank Sinatra begin his solo recording career?
1960s
1940s
1950s
1930s
After leaving the Tommy Dorsey Orchestra in 1942, Sinatra launched his solo recording career in the early 1940s. His initial solo hits, such as "All or Nothing at All," were recorded for Columbia Records during that decade. This period marked his rise as a standalone star.
For which record label did Sinatra record his early solo hits, including "All or Nothing at All"?
Reprise
Decca
Capitol
Columbia
Sinatra's early solo recordings were made for Columbia Records, where he produced hits like "All or Nothing at All" in 1943. His tenure at Columbia lasted through the mid-1950s before he moved to Capitol. These sessions shaped his signature vocal style.
Which career role is Frank Sinatra best known for?
Guitarist
Composer
Singer
Saxophonist
While Sinatra dabbled in acting and production, he was primarily celebrated as a singer. His phrasing, timing, and emotional delivery set new standards in vocal pop music. He influenced generations of performers with his unique singing style.
What was the title of Sinatra's first solo studio album, released in 1946?
Songs for Young Lovers
The Voice of Frank Sinatra
In the Wee Small Hours
Where Are You
Sinatra's debut studio album was "The Voice of Frank Sinatra," released by Columbia in 1946. It was one of the first 10-inch LPs and solidified his reputation as a solo artist. The album showcased his smooth crooning style.
Teenage fans who adored Sinatra in the 1940s were nicknamed what?
Croonerettes
Swing Kids
Bobby Soxers
Blue Eyes Brigade
Young female fans of Sinatra in the early 1940s were popularly referred to as "Bobby Soxers" due to their fashion choice of wearing rolled-down socks over their shoes. These devoted fans contributed to the first teen idol sensation in American pop culture.
What is Frank Sinatra's birth date?
December 14, 1915
January 12, 1915
November 12, 1915
December 12, 1915
Frank Sinatra was born on December 12, 1915. His birthday is celebrated each year by fans worldwide, and December 12 is recognized in Hoboken as Frank Sinatra Day. The date is well documented in biographies and official records.
What color were Sinatra's eyes?
Brown
Green
Blue
Hazel
Sinatra's striking blue eyes earned him the affectionate nickname "Ol' Blue Eyes." His eye color became a key part of his public persona and was frequently mentioned in the press. The nickname persists in popular culture.
What was the first album Sinatra recorded on his own label Reprise?
Ring-a-Ding-Ding!
Strangers in the Night
My Way
Francis Albert Sinatra & Antônio Carlos Jobim
Sinatra founded Reprise Records in 1960 to gain artistic control over his recordings. His first Reprise album, released in 1961, was "Ring-a-Ding-Ding!", arranged by Johnny Mandel. It marked a new phase in his career as label owner and artist.
Which arranger collaborated with Sinatra on the album "Songs for Swingin' Lovers!"?
Count Basie
Billy May
Nelson Riddle
Quincy Jones
Nelson Riddle arranged and conducted the sessions for "Songs for Swingin' Lovers!" in 1956. His upbeat, swinging orchestrations perfectly complemented Sinatra's lively vocal style. The collaboration is often cited as a high point of both men's careers.
Which song was famously played aboard Apollo 11 and recorded by Sinatra?
My Way
That's Life
New York, New York
Fly Me to the Moon
The Apollo 11 crew played "Fly Me to the Moon" during their mission in 1969 as they orbited the Moon. Sinatra's version, arranged by Quincy Jones for the 1964 album "It Might as Well Be Swing," became closely associated with space exploration.
In what year did Sinatra win an Academy Award for Best Supporting Actor?
1954
1955
1953
1956
Frank Sinatra won the Academy Award for Best Supporting Actor in 1954 for his role as Private Angelo Maggio in "From Here to Eternity." This Oscar marked a triumphant comeback after a slump in both his recording and film careers.
Which bandleader collaborated with Sinatra on the album "It Might as Well Be Swing"?
Count Basie
Benny Goodman
Artie Shaw
Duke Ellington
"It Might as Well Be Swing", released in 1964, featured the Count Basie Orchestra arranged by Quincy Jones. The album showcased a dynamic fusion of Sinatra's vocals with Basie's swinging big-band sound. It remains a classic collaboration.
Which song earned Sinatra the Grammy for Best Male Vocal Performance in 1967?
My Way
That's Life
Something
Strangers in the Night
"Strangers in the Night" won Sinatra the Grammy for Best Male Vocal Performance in 1967. The song became a huge hit, topping the charts and reaffirming his popularity in the rock era. It features lush orchestration and memorable lyrics by Charles Singleton and Eddie Snyder.
Which film featured Sinatra singing "Witchcraft"?
Pal Joey
High Society
Some Came Running
Young at Heart
Sinatra performed "Witchcraft" in the 1954 film "Young at Heart" opposite Doris Day. The song, written by Cy Coleman and Carolyn Leigh, became one of his signature numbers. Its sultry melody and Sinatra's playful delivery made it a classic.
Which U.S. president counted Sinatra among his close friends?
Lyndon B. Johnson
Jimmy Carter
John F. Kennedy
Richard Nixon
Frank Sinatra developed a close friendship with President John F. Kennedy during the early 1960s. Sinatra helped with JFK's campaign fundraising and even hosted events at his Palm Springs home. Their alliance symbolized the intersection of entertainment and politics.
What was the title of Sinatra's 1965 television special that garnered critical acclaim?
Sinatra: Live at the Palladium
Sinatra Sings America
A Man and His Music
Sinatra at the Sands
"A Man and His Music", broadcast in 1965 on NBC, was Sinatra's celebrated television special featuring his greatest hits. It earned Emmy nominations and showcased his charisma and repertoire. The success led to sequels and cemented his TV legacy.
Which song did Frank Sinatra perform as a duet with his daughter Nancy?
Something Stupid
Bang Bang
Then Soon I'll Be On My Way
Somethin' Stupid
"Somethin' Stupid" was recorded by Frank and Nancy Sinatra in 1967 and became a number-one hit. Written by C. Carson Parks, it remains one of the most successful father-daughter duets in pop music history. The chemistry between their vocals made it iconic.
Which Las Vegas hotel's showroom was closely associated with Sinatra's performances in the 1960s?
Caesars Palace
The Flamingo
The Sands
The Desert Inn
Sinatra headlined regularly at the Sands Hotel and Casino in Las Vegas during the 1960s. His close affiliation with the venue and his fellow Rat Pack entertainers made the Sands synonymous with high-profile Vegas entertainment. These appearances are legendary in showbiz lore.
Which entertainer was NOT an original member of Sinatra's Rat Pack?
Sammy Davis Jr.
Johnny Carson
Dean Martin
Peter Lawford
The core Rat Pack included Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop. Johnny Carson was not part of this group of entertainers. The Pack was famed for its Las Vegas shows and films of the 1960s.
In which country did Sinatra's recording of "My Way" reach number one on the national singles chart in 1969?
Australia
United Kingdom
Canada
United States
"My Way" topped the UK Singles Chart in 1969, though it peaked at number 27 on the US Billboard Hot 100. The song resonated strongly with British audiences and has remained a staple in the UK ever since.
Who arranged the music for Sinatra's Grammy-winning album "Come Dance with Me!" in 1959?
Quincy Jones
Nelson Riddle
Billy May
Gordon Jenkins
"Come Dance with Me!", released in 1959, was arranged by Billy May. His brassy, dynamic orchestrations helped the album win the Grammy for Album of the Year and Best Vocal Performance, Male. The collaboration steered Sinatra toward a more upbeat sound.
Why is Sinatra's "In the Wee Small Hours" album considered groundbreaking?
It was the first concept album
It featured only his original compositions
It was recorded live in one take
It was his first stereo release
"In the Wee Small Hours", released in 1955, is widely regarded as one of the first concept albums in pop music, unified by themes of loneliness and introspection. Sinatra curated the song selection to tell a cohesive emotional story - a novel approach at the time.
For which film did Sinatra receive his first Academy Award nomination for Best Actor?
The Man with the Golden Arm
Guys and Dolls
High Society
From Here to Eternity
Sinatra earned his first Best Actor nomination for his role as Frankie Machine in "The Man with the Golden Arm" (1955). Although he did win a Supporting Actor Oscar for "From Here to Eternity," this was his first nod in a leading capacity.
Which Brazilian musician collaborated with Sinatra on a 1967 bossa nova album?
Sérgio Mendes
Gilberto Gil
Antonio Carlos Jobim
João Gilberto
In 1967, Sinatra released "Francis Albert Sinatra & Antônio Carlos Jobim," a bossa nova album featuring the Brazilian composer Antonio Carlos Jobim. Their collaboration blended Sinatra's vocal style with Jobim's sophisticated Brazilian arrangements.
How many solo #1 hits did Sinatra secure on the Billboard Hot 100 chart?
3
4
1
2
On the Billboard Hot 100 (established in 1958), Sinatra achieved two solo number-one hits: "Strangers in the Night" (1966) and "Somethin' Stupid" (1967, duet with Nancy Sinatra). Despite his extensive catalog, these were his only chart-toppers on that specific listing.
Which of the following songs did Sinatra help co-write?
This Love of Mine
New York, New York
All or Nothing at All
My Way
Sinatra co-wrote "This Love of Mine" (1941) with Sol Parker and Hank Sanicola. While "My Way" and others were written by different songwriters, "This Love of Mine" is one of the few in his repertoire he had a hand in composing.
In what year did Sinatra announce his initial retirement from live performances?
1971
1974
1977
1969
Sinatra announced his retirement in July 1971 after concluding a run of shows at the Oakland Arena. Although he returned to performing in 1974, this initial farewell marked the end of his first major career phase.
Which city is referenced in Sinatra's song "Chicago (That Toddlin' Town)"?
Chicago
Los Angeles
Boston
New York
"Chicago (That Toddlin' Town)" is a song Sinatra made famous in his 1957 album "A Swingin' Affair!" The lyrics celebrate the city of Chicago's vibrancy and music scene. The tune remains a popular anthem for the city.
Which civilian honor was bestowed upon Sinatra by President Reagan in 1985?
Congressional Gold Medal
National Medal of Arts
Presidential Medal of Freedom
Kennedy Center Honors
Frank Sinatra received the Presidential Medal of Freedom from President Ronald Reagan in 1985, recognizing his contributions to American music and culture. This is the nation's highest civilian honor. Sinatra's acceptance speech underscored his gratitude and career reflections.
Who was Sinatra's musical conductor during his Sands Hotel performances in Las Vegas?
Antonio Morelli
Quincy Jones
Bill Miller
Nelson Riddle
Antonio Morelli served as the musical conductor for Sinatra's live shows at the Sands Hotel in Las Vegas throughout the 1960s. His orchestra backed Sinatra and fellow Rat Pack members. Morelli's arrangements contributed to the high-energy Vegas nightclub atmosphere.
What is the title of the 1990 Capitol box set that collected Sinatra's 1953-1960 recordings?
The Capitol Years
The Columbia Chronicles
The Ultimate Collection
Sinatra 80
Capitol Records released "The Capitol Years" box set in 1990, compiling Sinatra's recordings from 1953 to 1960. This three-disc collection highlights his most celebrated Capitol sessions, including hits like "I've Got You Under My Skin."
Who was Sinatra's long-time pianist and conductor, serving as musical director for over 30 years?
Nelson Riddle
Bill Miller
Gordon Jenkins
Count Basie
Bill Miller joined Sinatra's orchestra as pianist and conductor in 1951 and remained his trusted musical director until Sinatra's final performances in the 1990s. Miller's sensitive accompaniments and solos became a hallmark of Sinatra's live shows.
What is the name of the album featuring Sinatra duets with Bono, Aretha Franklin, and Elton John, released in 1993?
Duets II
My Way
Sinatra 1993
Duets
Released in 1993, "Duets" paired Frank Sinatra with contemporary artists like Bono, Aretha Franklin, and Elton John. The album was recorded by overdubbing Sinatra's vocals with guest artists, creating cross-generational collaborations. It was a commercial success, going multi-platinum.
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Study Outcomes

  1. Understand Sinatra's Musical Milestones -

    Trace the evolution of Frank Sinatra's career, highlighting his breakthrough hits and their impact on 20th-century music.

  2. Recall Iconic Songs and Albums -

    Memorize signature tunes like "I've Got You Under My Skin" and "My Way," reinforcing key entries in classic crooner music trivia.

  3. Analyze Hollywood Achievements -

    Examine Sinatra's major film roles and awards, understanding how his acting career complemented his status as Chairman of the Board.

  4. Identify Personal and Professional Milestones -

    Recognize notable events and collaborations that shaped Sinatra's legacy, from his Capitol Records era to Las Vegas headlining shows.

  5. Navigate Our Sinatra Trivia Quiz -

    Use the intuitive Frank Sinatra quiz online format to answer varied questions, track your score, and challenge fellow fans.

  6. Evaluate Your Crooner Expertise -

    Reflect on your quiz results to determine how well you know Frank Sinatra and discover areas for further exploration.

Cheat Sheet

  1. Early Career Breakthrough -

    Sinatra first soared to fame in 1939 as the lead singer for Harry James's big band, scoring his first hit with "I'll Never Smile Again." Remember the year 1939 by linking it to the start of World War II for an easy mnemonic. These roots set the stage for all your frank sinatra trivia success.

  2. Signature Swing Classics -

    Frank Sinatra's swing era hits like "Come Fly with Me" and "Fly Me to the Moon" were arranged by Nelson Riddle and helped define the Great American Songbook. Use the mnemonic "MoonFly" to recall both titles easily during a sinatra trivia quiz. These tunes showcase his smooth phrasing and timeless style.

  3. Hollywood & Awards -

    In 1953, Sinatra won an Academy Award for Best Supporting Actor in From Here to Eternity, solidifying his status as a crossover star. Note the year by linking it to the end of the Korean War for easy recall. This achievement often appears in frank sinatra quiz online questions.

  4. Record Labels & Collaborations -

    Throughout his career, Sinatra recorded with three major labels - Columbia, Capitol, and his own Reprise Records - known as the "CCR" sequence for easy memorization. He also collaborated with jazz legends like Count Basie and Antônio Carlos Jobim, enriching his repertoire. Remember "CCR" to ace classic crooner music trivia.

  5. Legacy & Grammy Achievements -

    Sinatra earned nine Grammy Awards, including the Lifetime Achievement Award, and has several entries in the Grammy Hall of Fame, testimony to his enduring impact. His nickname "Ol' Blue Eyes" and countless covers of his songs keep his legacy alive. These facts are essential for how well do you know frank sinatra challenges.

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