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01
After his vocal cords hemorrhaged in 1953, Sinatra briefly lost the ability to sing. When his voice returned, it had an extra dimension that many fans believed made his singing better.
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02
In 1963, his son Frank Sinatra Jr. was kidnapped. The kidnappers told Sinatra to call from pay phones; during one call he ran out of coins and feared it had cost him his son. He paid the $250,000 ransom, Frank Jr. was returned, and the kidnappers were caught. Sinatra carried a roll of dimes until his death.
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03
When Bela Lugosi died virtually penniless, Sinatra quietly paid for his funeral.
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04
Brad Dexter saved Sinatra and Ruth Koch from drowning during production of None But the Brave 1965 in Kauai, Hawaii. Dexter was later awarded a Red Cross medal for his bravery, and the two stayed close friends for life.
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05
Sinatra served as a mentor to Harry Connick Jr., whom he called The Kid.
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06
He and the other Rat Pack members were banned from Marilyn Monroe’s funeral by Joe DiMaggio.
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07
Sinatra refused to stay or perform at any hotel that would not allow Sammy Davis Jr. or any other African-American to enter.
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08
According to Mia Farrow’s biography, Sinatra offered to have Woody Allen’s legs broken after Allen had an affair with Farrow’s adopted daughter Soon-Yi Previn.
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09
Sinatra’s personality could be sweet one minute and nasty the next, leading some to theorize he was bipolar.
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10
Frank Capra believed Sinatra had the potential to be the greatest actor ever and urged him to quit music and focus solely on acting.
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11
A paparazzo snooping around Sinatra’s house found himself face-to-face with Sinatra and, terrified, jumped into a pool despite being unable to swim. Sinatra had to fish him out.
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12
Sinatra was generous with drivers, often tipping in excess of $100.
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13
His version of New York, New York is played at Yankee Stadium after every home win; Liza Minnelli’s version is played after every home loss.
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14
Weighing over 13 pounds at birth, Sinatra was delivered by forceps, nearly severing one ear. He appeared lifeless but was revived when his grandmother held him under cold running water.
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15
When he first met Mia Farrow in 1964, he was 48 and she was 19, prompting Dean Martin to quip that he owned a bottle of Scotch older than Farrow.
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16
By 1951, Sinatra was broke; Ava Gardner paid for his plane ticket to join her in Africa for Mogambo 1953.
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17
In 1966, given the song Strangers in the Night, Sinatra despised it after one read. It turned into one of his biggest hits, yet he still derided it at every opportunity.
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18
Sinatra was a fan of Magnum, P.I. and appeared as a guest star in 1986 at his own request, insisting on a fight scene. His expenses, including his jet and entourage, cost $300,000.
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19
He inspired the Johnny Fontaine character in The Godfather 1972.
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20
At his funeral, items placed in his coffin included ten dimes, Tootsie Roll candies, Black Jack gum, a roll of Life Savers, a ring engraved with Dream, a mini Jack Daniels bottle, a pack of Camel cigarettes, and a Zippo lighter.
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21
While filming a kidnapping scene for Robin and the 7 Hoods 1964, Sinatra learned his son had been kidnapped; the scene was never used.
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22
Sinatra and Paul Newman are the only people to win an Honorary Oscar, a Jean Hersholt Humanitarian Award, and a competitive Oscar.
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23
Despite criticizing rock music, Sinatra admired The Beatles’ Something, covering it in concerts, and offered to write a second stanza for Chicago’s Color My World.
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24
The epitaph on his headstone reads The best is yet to come.
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25
Sinatra had a longstanding dislike of Marlon Brando from their time in Guys and Dolls 1955; he nicknamed Brando Mr. Mumbles, while Brando called him Mr. Baldy.
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26
He reportedly kept a picture of Ava Gardner on his mirror long after their breakup.
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27
A forceps delivery at birth left permanent scars on his cheek and ruptured an eardrum, the latter often cited as the reason he was exempted from military service during World War II.
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28
While filming a fight scene in The Manchurian Candidate 1962, Sinatra permanently injured his little finger by breaking it through a solid wooden table; the footage was kept.
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29
Sinatra is one of only five actors to have both a #1 single and an Oscar for acting, alongside Cher, Barbra Streisand, Jamie Foxx, and Bing Crosby.
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30
He made no public appearances after suffering a heart attack in January 1997.
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31
While filming a funeral scene in Robin and the 7 Hoods 1964, Sinatra learned that President John F. Kennedy had been killed earlier that day.
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32
In 1960, Sinatra refused to pay a 50-cent parking fee at Capitol Records; the attendant had his car towed.
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33
Sinatra was instrumental in reuniting Jerry Lewis and Dean Martin after decades of estrangement. During Lewis’s telethon, Sinatra escorted Martin onstage, shocking Lewis.
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34
On his last day of life May 14, 1998, traffic was unusually light as many Americans were watching the finale of Seinfeld, allowing his family to rush him to the hospital.
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35
In 1974, after a tirade against Australian press, Sinatra was refused service by aviation unions. He was spirited away at night after intervention by a union leader.
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36
Sinatra did not want to record My Way, thinking it self-serving, but it became his signature closing song.
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37
His will includes a clause that anyone contesting it is automatically disinherited.
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38
Sinatra saw Steve McQueen in Wanted: Dead or Alive and requested him for Never So Few 1959. McQueen declined Ocean’s Eleven 1960 on advice of critic Hedda Hopper, ending their brief friendship.
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39
Sinatra was a strong supporter of Jewish causes, donating over $1 million to Hebrew University, which dedicated the Frank Sinatra International Student Center. His movies and records were banned in some Arab countries.
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40
He walked off the set of Carousel 1956 on the first day after learning each scene would be shot twice with different lens sizes, saying he was paid to make one movie, not two.
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41
Von Ryan’s Express 1965 was his most successful film of the 1960s, grossing over $17 million.
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42
Sinatra became estranged from Dean Martin after Martin quit The Together Again Tour.
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43
After President Kennedy chose not to stay with Sinatra due to his Mafia ties, Sinatra’s relationship with him soured.
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44
He divorced Mia Farrow after she refused to quit filming Rosemary’s Baby 1968 to co-star in The Detective; divorce papers were delivered to her on set.
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45
Sinatra was the first choice for Dirty Harry 1971 but broke his finger and had to drop out.
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46
He owned an extensive collection of electric toy trains, set up to weave through a replica of the Hoboken train station.
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47
Lee J. Cobb credited Sinatra with saving his life after Cobb’s HUAC testimony; Sinatra got him a role in The Miracle of the Bells and paid his hospital bills.
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48
Sinatra was named Entertainer of the Century in 2000.