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