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