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