Frank Sinatra - Quiz
Frank Sinatra
  • 1. Which album topped the Billboard chart in October 1960?
A) Nice 'n' Easy
B) Sinatra and Strings
C) Ring-a-Ding-Ding!
D) The Concert Sinatra
  • 2. With whom did Sinatra feud while at Capitol Records?
A) Don Costa
B) Nelson Riddle
C) Alan W. Livingston
D) Norman Granz
  • 3. What jazz label did Sinatra initially attempt to purchase?
A) Reprise Records
B) Verve Records
C) Columbia Records
D) Capitol Records
  • 4. Which of these arrangers did Sinatra work with after forming Reprise?
A) Billy May
B) Neil Hefti
C) Gordon Jenkins
D) Nelson Riddle
  • 5. What did Reprise Records guarantee its artists?
A) Complete ownership of their work
B) Guaranteed radio airplay
C) Automated royalty payments
D) Lifetime concert bookings
  • 6. For how much money did Sinatra eventually sell Reprise Records?
A) $50 million
B) $100 million
C) $25 million
D) $80 million
  • 7. What was the title of Sinatra's first album on Reprise Records?
A) Ring-a-Ding-Ding!
B) Softly, as I Leave You
C) That's Life
D) Sinatra-Basie
  • 8. Which album served as Sinatra's final contractual commitment to Capitol?
A) Nice 'n' Easy
B) Point of No Return
C) The Concert Sinatra
D) September of My Years
  • 9. Who arranged the 1962 album Sinatra and Strings?
A) Neil Hefti
B) Don Costa
C) Nelson Riddle
D) Quincy Jones
  • 10. With which jazz musician did Sinatra record the 1962 album Sinatra-Basie?
A) Sammy Davis Jr.
B) Count Basie
C) Ben Webster
D) Joe E. Lewis
  • 11. Where did Sinatra and Count Basie perform together in 1965?
A) Carnegie Hall
B) Hollywood Bowl
C) Newport Jazz Festival
D) Madison Square Garden
  • 12. Which album featured a 73-piece symphony orchestra and was recorded on 35 mm film?
A) Strangers in the Night
B) That's Life
C) September of My Years
D) The Concert Sinatra
  • 13. In which song did Sinatra "darken the hue" of his vocals?
A) Strangers in the Night
B) Ol' Man River
C) That's Life
D) My Kind of Town
  • 14. Which song was nominated for the Academy Award for Best Original Song in 1964?
A) My Kind of Town
B) It Was a Very Good Year
C) That's Life
D) Strangers in the Night
  • 15. What was the purpose of the collection America, I Hear You Singing?
A) A tribute to John F. Kennedy
B) A fundraiser for Reprise Records
C) Support for Mexican charities
D) A celebration of the Rat Pack
  • 16. Where was the Frank Sinatra International Youth Center for Arab and Jewish children dedicated?
A) New York
B) Nazareth
C) Los Angeles
D) Mexico City
  • 17. Which album won the Grammy Award for best album of the year in 1965?
A) September of My Years
B) That's Life
C) A Man and His Music
D) Sinatra and Strings
  • 18. Which single from September of My Years won a Grammy for Best Vocal Performance, Male?
A) My Kind of Town
B) It Was a Very Good Year
C) That's Life
D) Strangers in the Night
  • 19. Which 1966 album produced a Top Ten hit single of the same name?
A) September of My Years
B) A Man and His Music
C) Sinatra-Basie
D) That's Life
  • 20. Which song won the Grammy Award for Record of the Year?
A) That's Life
B) Strangers in the Night
C) My Kind of Town
D) It Was a Very Good Year
  • 21. How did Frank Sinatra learn music as a teenager?
A) Through formal conservatory training
B) By reading sheet music
C) By ear
D) From his father
  • 22. What was the name of the singing group Sinatra joined in 1935?
A) The 3 Flashes
B) The Secaucus Cockamamies
C) Hoboken Four
D) The Bayonne Bacalas
  • 23. Who arranged Sinatra's first solo studio recording of 'Our Love'?
A) Frank Mane
B) Hank Sanicola
C) Harry James
D) Tommy Dorsey
  • 24. In 1939, what was Sinatra's weekly salary under his contract with Harry James?
A) $75
B) $12.50
C) $125
D) $650
  • 25. Which band did Sinatra leave the Harry James group to join in November 1939?
A) The Hoboken Four
B) The Count Basie orchestra
C) Tommy Dorsey band
D) The Major Bowes orchestra
  • 26. What hobby did Sinatra adopt from Tommy Dorsey?
A) Collecting stamps
B) Horse racing
C) Playing saxophone
D) Toy trains
  • 27. Who did Sinatra ask to be the godfather of his daughter Nancy?
A) Tommy Dorsey
B) Hank Sanicola
C) Harry James
D) Willie Moretti
  • 28. Which song was Sinatra's first top-10 hit?
A) Our Love Affair
B) Imagination
C) Polka Dots and Moonbeams
D) I'll Never Smile Again
  • 29. What percentage of Sinatra's lifetime earnings did his contract with Tommy Dorsey require him to pay?
A) 50%
B) 10%
C) 43%
D) 25%
  • 30. Who did Sinatra hire as his personal arranger after leaving the Tommy Dorsey band?
A) Frank Mane
B) Hank Sanicola
C) Axel Stordahl
D) Buddy Rich
  • 31. Who was the drummer that was friends with Sinatra but also a rival for stardom in the Dorsey band?
A) Dick Haymes
B) Buddy Rich
C) Jack Leonard
D) Fred Tamburro
  • 32. What was the name of the radio show where the Hoboken Four won first prize?
A) Major Bowes Amateur Hour
B) The Sands Broadcast
C) Dance Parade
D) Jersey City Radio Hour
  • 33. Which singer replaced Sinatra in the Tommy Dorsey band?
A) Dick Haymes
B) Jack Leonard
C) Buddy Rich
D) Frank Mane
  • 34. Which artist did Sinatra feel an 'insatiable desire' to compete with?
A) Harry James
B) Tommy Dorsey
C) Count Basie
D) Bing Crosby
  • 35. In what year did Sinatra join the Harry James band?
A) 1946
B) 1939
C) 1935
D) 1941
  • 36. With which musician did Sinatra record an album in 1968?
A) Duke Ellington
B) Tom Jobim
C) Count Basie
D) Nelson Riddle
  • 37. What was the name of the anti-war drama directed by Sinatra in 1965?
A) None but the Brave
B) On the Town
C) The Detective
D) Tony Rome
  • 38. Which music critic called Sinatra the greatest singer of the 20th century?
A) Nelson Riddle
B) Harry James
C) Robert Christgau
D) Tom Jobim
  • 39. In what year did Frank Sinatra pass away?
A) 2001
B) 1988
C) 1998
D) 1995
  • 40. How many Grammy Awards did Sinatra earn in his career?
A) 10
B) 5
C) 20
D) 13
  • 41. Which song did Sinatra release in 1980?
A) The Voice
B) My Way
C) New York, New York
D) September of My Years
  • 42. Which film won Sinatra a Golden Globe Award?
A) Guys and Dolls
B) On the Town
C) High Society
D) Pal Joey
  • 43. On what date was Frank Sinatra born?
A) December 12, 1912
B) December 12, 1915
C) January 15, 1917
D) November 20, 1915
  • 44. What caused the scarring on Sinatra's left cheek and neck at birth?
A) A childhood accident
B) A fall from a staircase
C) Cystic acne
D) Forceps used during delivery
  • 45. Sinatra's father, Marty, was originally from which location?
A) Lercara Friddi, Sicily
B) Genoa, Liguria
C) Hoboken, New Jersey
D) Naples, Italy
  • 46. What was Sinatra's mother's name?
A) Barbara Sinatra
B) Natalina "Dolly" Garaventa
C) Dolly Hoboken
D) Maria Martino
  • 47. What religious upbringing did Sinatra receive?
A) Catholic Church
B) Greek Orthodox
C) Jewish faith
D) Protestant Church
  • 48. What was Marty Sinatra's profession before becoming a fire captain?
A) Journalist
B) Civil engineer
C) Bantamweight boxer
D) Riveter
  • 49. What instrument did Sinatra receive for his 15th birthday?
A) A piano
B) A ukulele
C) A guitar
D) A banjo
  • 50. Why was Sinatra expelled from A. J. Demarest High School?
A) Poor grades
B) Skipping classes
C) Fighting
D) General rowdiness
  • 51. What was Sinatra's first job after leaving Drake Business School?
A) Firefighter
B) Singer
C) Riveter
D) Delivery boy
  • 52. Where did Sinatra work as a riveter?
A) Stevens Institute
B) Tietjen and Lang shipyard
C) Jersey Observer
D) Hoboken Fire Department
  • 53. How long did Sinatra attend Drake Business School?
A) 2 years
B) 6 months
C) 47 days
D) 11 months
  • 54. Who provided money to Sinatra for clothes during the Great Depression?
A) His uncle Domenico
B) His mother, Dolly
C) His father, Marty
D) His godfather Frank
  • 55. What nickname was given to the subculture of teenage girl fans of Sinatra?
A) Paramount girls
B) Sinatratics
C) The Voice fans
D) Bobby soxers
  • 56. Who was the publicist responsible for depicting Sinatra as a vulnerable, shy, Italian–American?
A) Alec Wilder
B) Jack Benny
C) Bob Weitman
D) George Evans
  • 57. What was the name of the near riot that occurred outside the Paramount in 1944?
A) Bobby Soxer Riot
B) Columbus Day Riot
C) Paramount Theatre Riot
D) Sinatramania Riot
  • 58. Why was Sinatra rejected from military service during World War II?
A) He was already a famous entertainer
B) He paid $40,000 to avoid service
C) Physical health issues
D) Not acceptable from a psychiatric viewpoint
  • 59. Which comedian accompanied Sinatra on his USO tours?
A) Jack Benny
B) Bing Crosby
C) Bob Weitman
D) Phil Silvers
  • 60. On what date did Sinatra sign with Columbia Records?
A) October 12, 1944
B) January 1, 1946
C) June 1, 1943
D) December 30, 1942
  • 61. Which song reached number 2 on the charts after its re-release by Columbia in 1943?
A) The Coffee Song
B) Nancy (with the Laughing Face)
C) White Christmas
D) All or Nothing at All
  • 62. Who was hired as an arranger and conductor for sessions with the Bobby Tucker Singers?
A) George Evans
B) Harry James
C) Phil Silvers
D) Alec Wilder
  • 63. What record did Sinatra record with the Metronome All-Stars in 1947?
A) Sweet Lorraine
B) The Coffee Song
C) Day by Day
D) Mam'selle
  • 64. What was the maximum amount Sinatra was earning per week by 1946?
A) $40,000
B) $50,000
C) $10,000
D) $93,000
  • 65. What instrument did Nat King Cole play on the track 'Sweet Lorraine'?
A) Drums
B) Piano
C) Saxophone
D) Guitar
  • 66. Which actress was Sinatra involved in a highly publicized affair with during his career slump?
A) Natalie Wood
B) Grace Kelly
C) Ava Gardner
D) Nancy Sinatra
  • 67. Where did Sinatra make his Las Vegas debut in September 1951?
A) Desert Inn
B) Copa Club
C) Sands Hotel and Casino
D) Chez Paree
  • 68. Which executive at Columbia Records claimed he 'couldn't give away' Sinatra records?
A) Mitch Miller
B) Alan Livingston
C) Jack Entratter
D) Percy Faith
  • 69. What award did Sinatra win for his role in 'From Here to Eternity'?
A) Golden Globe for Best Actor
B) Grammy Award for Album of the Year
C) Academy Award for Best Supporting Actor
D) Billboard Favorite Male Vocalist
  • 70. Which song did Sinatra exclaim 'I'm back, baby, I'm back!' after recording with Nelson Riddle?
A) Young at Heart
B) I've Got the World on a String
C) My Funny Valentine
D) A Foggy Day
  • 71. Which album, released in 1958, was designed as a musical world tour?
A) Come Fly with Me
B) Close to You
C) Come Dance with Me!
D) Only the Lonely
  • 72. Which album won the Grammy Award for Album of the Year in 1959?
A) Come Dance with Me!
B) Frank Sinatra Sings for Only the Lonely
C) No One Cares
D) A Swingin' Affair!
  • 73. Who was the arranger for the 1957 album 'Where Are You?'?
A) Gordon Jenkins
B) Nelson Riddle
C) Billy May
D) Axel Stordahl
  • 74. Who conducted the music for 'Sinatra at the Sands'?
A) Quincy Jones
B) Johnny Hodges
C) Claude François
D) Paul Anka
  • 75. With which artist did Sinatra record a Grammy-nominated album in 1967?
A) Duke Ellington
B) Paul Simon
C) Antônio Carlos Jobim
D) Paul Anka
  • 76. Which song on 'The World We Knew' is a chart-topping duet with Nancy Sinatra?
A) Somethin' Stupid
B) Yesterday
C) My Way
D) Indian Summer
  • 77. Who wrote the lyrics for the song 'My Way'?
A) Ervin Drake
B) Claude François
C) Jacques Revaux
D) Paul Anka
  • 78. In what year did Sinatra record 'My Way'?
A) 1969
B) 1967
C) 1968
D) 1966
  • 79. According to NPR, what is 'My Way' frequently used for?
A) Weddings
B) Graduations
C) Funerals
D) Political rallies
  • 80. Which of these songs did Sinatra record in 1969 to maintain commercial viability?
A) Comme d'habitude
B) Somethin' Stupid
C) Yesterday
D) Indian Summer
  • 81. Which concept album did Sinatra release in 1970 with music by Bob Gaudio?
A) Trilogy
B) The Main Event
C) Watertown
D) She Shot Me Down
  • 82. What song did Sinatra sing at his 1971 retirement concert just before disappearing from the stage?
A) New York, New York
B) Angel Eyes
C) That's Life
D) My Kind of Town
  • 83. What was the name of the holiday home Sinatra designed near Palm Desert?
A) Palm Springs Retreat
B) The Sinatra Estate
C) Blue Eyes Manor
D) Villa Maggio
  • 84. Who did Sinatra reunite with for the 1973 television special Magnavox Presents Frank Sinatra?
A) Dean Martin
B) Count Basie
C) Gene Kelly
D) Jerry Lewis
  • 85. Which bandleader backed Sinatra for the 1974 Madison Square Garden concert?
A) Gordon Jenkins
B) Count Basie
C) Woody Herman
D) Don Costa
  • 86. With whom did Sinatra record for the last time on March 14, 1977?
A) Nelson Riddle
B) Vinnie Falcone
C) Don Costa
D) Gordon Jenkins
  • 87. What is the title of the 1980 triple album released by Sinatra?
A) Trilogy: Past Present Future
B) The Main Event
C) She Shot Me Down
D) Ol' Blue Eyes Is Back
  • 88. In what city was the 1972 rally held where Sinatra sang for Richard Nixon?
A) Las Vegas
B) New York
C) Chicago
D) Los Angeles
  • 89. Which term did Kelley use to describe Sinatra's voice in the early 1980s?
A) Loamier
B) Metallic
C) Brittle
D) Fragile
  • 90. Which president honored Sinatra at the 1983 Kennedy Center Honors?
A) Jimmy Carter
B) George H.W. Bush
C) Ronald Reagan
D) Richard Nixon
  • 91. What medical condition caused Sinatra to collapse on stage in 1986?
A) Pneumonia
B) Stroke
C) Diverticulitis
D) Heart failure
  • 92. Who introduced Sinatra at the 1994 Grammy Awards?
A) Quincy Jones
B) Bono
C) Dean Martin
D) Ella Fitzgerald
  • 93. How many concerts did Sinatra perform in 1992?
A) 73
B) 90
C) 84
D) 65
  • 94. What was Sinatra's best-selling album released in 1993?
A) L.A. Is My Lady
B) Duets II
C) Duets
D) The Reprise Collection
  • 95. Where were Sinatra's final public concerts held?
A) New York City
B) Fukuoka Dome, Japan
C) Palm Desert
D) Las Vegas
  • 96. When did Sinatra sing for the last time before a live audience?
A) January 1, 1996
B) December 20, 1994
C) February 25, 1995
D) June 6, 1988
  • 97. What color did the Empire State Building glow for Sinatra's 80th birthday?
A) White
B) Blue
C) Red
D) Gold
  • 98. In what year was Sinatra elected to the Gaming Hall of Fame?
A) 1995
B) 1983
C) 1997
D) 1994
  • 99. Who was Sinatra's personal favorite classical composer?
A) Puccini
B) Ralph Vaughan Williams
C) Alec Wilder
D) Antonio Jobim
  • 100. Who did Sinatra later believe was the best singer in the business?
A) Tony Bennett
B) Alec Wilder
C) Bing Crosby
D) Sammy Cahn
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