- Briefly lost the ability to sing after his vocal cords hemorrhaged in 1953. When his voice returned it had an extra dimension which many fans believed made his singing better than before.
- In 1963 his son Frank Sinatra Jr. was kidnapped. The kidnappers told Frank Sr. to call them from pay phones. During one call he ran out of coins, and briefly feared that it had cost him his son (the kidnappers gave him another chance). He paid the $250,000 ransom, Frank Jr. was returned and the kidnappers were eventually caught. However, as a result of the incident, he swore never to be caught without dimes again and carried a roll with him until his death.
- Refused to stay or perform at any hotel that wouldn't allow Sammy Davis Jr. or any other African-American to enter.
- When Bela Lugosi died virtually penniless, Sinatra quietly paid for his funeral.
- On 5/10/1964, Brad Dexter (The Magnificent Seven (1960), among others) saved both Sinatra's life and that of Ruth Koch (wife of producer Howard W. Koch) during production of the World War II film None But the Brave (1965) in Kaui, HI. They were swimming at a beach when they were swept out to sea by the outgoing tide and nearly drowned in high, billowing waves. Dexter swam out and rescued them together, but they were not able to reach shore for nearly 45 minutes. In the waves, Sinatra reportedly became separated and murmured, "It's all over . . . please take care of my kids . . . I'm going to die . . . " Both Sinatra and Koch then fell unconscious for several minutes before two surfers arrived to help Dexter take them to shore. Dexter was later awarded a Red Cross medal for his bravery. Sinatra never forgot it and the two stayed close friends for the rest of their lives.
- Served as a mentor to Harry Connick Jr., whom he referred to as "The Kid".
- He and the other members of the Rat Pack were banned from Marilyn Monroe's funeral by Joe DiMaggio
- Weighed over 13 pounds at birth, and had to be delivered by forceps. As a result, one of his ears was nearly severed. Showing no signs of life, he was held by his grandmother under cold running water. He began to breathe and cry. His mother-- a practical nurse--and his father, a tavern operator, had been hoping for a girl and had already chosen the name Frances. So they gave him the masculine form of the name: Francis.
- According to Mia Farrow's biography, "What Falls Away", he offered to have Woody Allen's legs broken when it was discovered that he was having an affair with Farrow's adopted daughter, Soon-Yi Previn (whom Allen later married).
- Known for his mercurial personality, as all those who were close to him knew; he could be as sweet as a person could be one minute and equally as nasty and violent in the next moment. Some theorized that he was bipolar.
- He inspired the Johnny Fontaine character in The Godfather (1972).
- Had a longstanding dislike of Marlon Brando from the time they starred in Guys and Dolls (1955). Sinatra always felt he should have played Brando's part, with Gene Kelly in the other role. Sinatra nicknamed Brando "Mr. Mumbles" while Brando called him "Mr. Baldy".
- Frank Capra claimed that Sinatra had the potential to be the best actor there ever was. He once told Frank to quit his musical career and concentrate solely on acting and that if he did he would go down as the greatest actor who ever lived.
- Known to be very generous with drivers and often tipped in excess of $100, usually much more than they were making for driving him.
- At his funeral, friends and family members placed items in his coffin that had personal references. These are reported to include ten dimes, several Tootsie Roll candies, a pack of Black Jack chewing gum, a roll of wild cherry Life Savers candy, a ring engraved with the word "Dream", a mini bottle of Jack Daniels whiskey, a pack of Camel cigarettes and a Zippo cigarette lighter.
- Paparazzi were very aware of his legendary temper. One memorable account by Tina Sinatra has a paparazzi snooping around her dad's house, then suddenly finding himself nose-to-nose with Frank himself. Terrified, the photographer leaped into a pool (despite being unable to swim), requiring Frank to fish him out.
- His version of "New York, New York" is played at Yankee Stadium after every Yankee home win. Liza Minnelli's version is played after every Yankee home loss.
- The epitaph on his headstone reads "The best is yet to come."
- While visiting Capitol Records in 1960, he refused to pay the 50-cent entry fee at the parking garage. The attendant had his car towed.
- He was broke by 1951. Ava Gardner had to pay for his plane ticket so he could accompany her to Africa, where she shot Mogambo (1953).
- When he first met Mia Farrow in 1964, he was 48 and she was 19, a fact that prompted Dean Martin to quip that he owned a bottle of Scotch older than Farrow.
- While filming a funeral scene in Robin and the 7 Hoods (1964), he learned that his close friend and benefactor, President John F. Kennedy, had been killed in Dallas earlier that day.
- Was a fan of Magnum, P.I. (1980) and wanted to appear as a guest star. Through Larry Manetti a message was delivered to producer/star Tom Selleck for Selleck to give Frank a call. When hr called, Frank told him that he wanted to appear on "Magnum", but that Tom should not worry, because he did not want to be paid, he just wanted his expenses paid. Selleck agreed and asked Frank what kind of story line he wanted for his character. Frank said that he did not care, as long as his character was a tough guy, and that there be a fight scene where he knocks someone out. Selleck agreed to Frank's terms and concept for the character Frank would play, and he did appear on the show in 1986, in what would be his last, full acting, non-cameo role. His "expenses" turned out to be a problem for the producers and CBS (the network that aired the show during its original broadcast run), because Frank's expenses included the costs for his personal jet and his full entourage. The final tally was $300,000.
- He and Paul Newman are the only people to win an Honorary Oscar, a Jean Hersholt Humanitarian Award and a competitive Oscar.
- On 5/14/98, his last day of life, his family drove him to the hospital, frantically running stop signs and red lights. However, traffic was unusually light at that time, since many Americans were at home watching the final episode of the TV show Seinfeld (1989).
- While filming a kidnapping scene for Robin and the 7 Hoods (1964), he learned that his son, singer Frank Sinatra Jr., had been kidnapped from his hotel room in Lake Tahoe, NV. For obvious reasons, the scene was never used in the completed film.
- In 1966 he was given a song to record, and after reading it over once, he despised it. The song was "Strangers in the Night", which turned out to be one of his biggest hits. Even after its success, he still hated the song and took every opportunity to deride it.
- Reportedly kept a picture of Ava Gardner on his mirror long after their breakup.
- Although he criticized rock music on several occasions, he expressed admiration for several artists in the genre. He called "Something", written by George Harrison and performed by The Beatles, one of his favorite songs and covered it at his concerts. He was such a big fan of Chicago's song "Color My World" that he offered to write a second stanza to it. He also enthusiastically embraced the Irish rock band U2 when they visited the US.
- A forceps delivery at his birth left permanent scars on his cheek and ruptured an eardrum. The latter is the reason most often given for his being exempted from military service during World War II.
- Permanently injured one of his fingers while shooting a fight scene with Henry Silva in The Manchurian Candidate (1962). In the scene, Sinatra threw a karate chop and his hand went through a solid wooden table, breaking several bones in his little finger. The footage was left in the final cut.
- Throughout his life he was a strong supporter of Jewish causes. He stepped forward in the early 1940s, when big names were needed to rouse America into saving Europe's remaining Jews, and he sang at an "Action for Palestine" rally (1947). He sat on the board of trustees of the Simon Wiesenthal Center; and he donated over $1 million to Jerusalem's Hebrew University, which honored him by dedicating the Frank Sinatra International Student Center. As a result of his support for the Jewish state, his movies and records were banned in some Arab countries.
- One of only five actors/actresses to have both a #1 single and an Oscar for acting. The others are Cher, Barbra Streisand, Jamie Foxx, and Bing Crosby.
- Made no further public appearances after suffering a heart attack in January 1997.
- Was originally signed on to play Billy Bigelow in Carousel (1956), but walked off the set on the first day of filming after he found out that they were going to shoot each scene twice, using two different lens sizes, and was quoted as saying, "I was paid to make one movie, not two".
- Was instrumental in reuniting Jerry Lewis and Dean Martin after their decades of estrangement. During an appearance on Lewis' annual telethon for Muscular Dystrophy, Sinatra said that he had a friend who wanted to say hello; then, he escorted Martin onto the stage to a flabbergasted Lewis. The two remained reunited until Martin's death.
- While on a tour in 1974 which included Australia, Sinatra became enraged by his treatment by members of the Australian press. After a brief scuffle at the airport, he appeared on stage and delivered a hateful tirade against the press, calling them "bums and parasites," and calling the female reporters "buck-and-a-half hookers." In retaliation, the aviation union refused to refuel or otherwise maintain his private jet until he apologized. He never did. He was spirited away in the night after intervention by a high-level union leader.
- A provision in his will is that if anyone contests it, they are automatically disinherited.
- Although he is most associated with the song "My Way", he didn't originally want to record it because he thought it was "self-serving and indulgent". Although he disliked the song, his persona became so associated with it that he ended every concert with it. It was famously parodied for a 1978 single by the British punk rock band Sex Pistols.
- He saw Steve McQueen in his western TV series Wanted: Dead or Alive (1958) and requested him to take Sammy Davis Jr.'s role in Never So Few (1959). Davis had said in an interview he thought he was bigger than Sinatra in the entertainment world at that time. Since Davis' role in the film was originally written as a sidekick, it had to be re-written somewhat for McQueen. During filming, they got along so well that Sinatra wanted McQueen to appear in Ocean's Eleven (1960) as the cowboy Louis Jackson. McQueen was all for it but was convinced otherwise by critic Hedda Hopper, who told him it would not be a wise career move to be known as a Sinatra flunky. McQueen passed on the film, and although there were no hard feelings his brief friendship with Sinatra came to an end.
- Was the first choice to play the title role in Dirty Harry (1971), but broke his finger before shooting started and had to bow out of the production.
- Divorced his third wife Mia Farrow after she refused to quit filming Rosemary's Baby (1968) in order to co-star with him in the "Rat Pack" crime drama The Detective (1968). He had the divorce papers delivered to her on set.
- He owned an extensive collection of electric toy trains. He had coveted electric trains as a boy and set up a track that wove through the path of his career. The train started at a replica of the Hoboken train station.
- Lee J. Cobb credited Sinatra with saving his life after his career was nearly ruined by his defiance of the House Un-American Activities Committee investigating Communist "subversion" in the film industry. Cobb had defied HUAC for two years, after being named as a supposed Communist by Larry Parks in 1951. During those two years, Cobb's once-flourishing career floundered and his wife had to be institutionalized after having a mental breakdown. Finally,he agreed to testify as a "friendly" witness, appearing before HUAC in 1953. At the conclusion of his testimony, he praised the committee. Soon after his appearance there he had a massive heart attack. Sinatra--who barely knew Cobb--got him a part in his film The Miracle of the Bells (1948) when no other studio would hire him. In addition, knowing that Cobb was broke, Sinatra paid his hospital bills, then had Cobb stay with him before renting him a luxurious apartment. Cobb believes that Sinatra identified with him as a troubled artist down on his luck, as Sinatra's own career had been in a severe tailspin before he resurrected himself by winning an Oscar for From Here to Eternity (1953). Cobb later said that if it wasn't for Sinatra, he didn't think he would have come through that period alive. Sinatra told Cobb he thought that he was "robbed" when he failed to win the Oscar for his performance as Johnny Friendly in On the Waterfront (1954) (ironically, Sinatra originally had been scheduled to star in the picture, which was filmed in his hometown of Hoboken, NJ, but producer Sam Spiegel gave the role to Marlon Brando when he realized he could raise $1 million in financing for the picture by using Brando versus $500,000 if Sinatra was the star).
- Was the leader of the "Rat Pack"--Dean Martin, Frank Sinatra, Sammy Davis Jr., Peter Lawford and Joey Bishop. All appeared in Ocean's Eleven (1960) and Sergeants 3 (1962).
- Became estranged from Dean Martin during the final years of their lives after Martin quit "The Together Again Tour".
- Was a great admirer of John F. Kennedy, campaigning for him in the 1960 presidential election and organizing his inauguration ball on 1/20/1961. In August 1962 Kennedy decided not to stay with Sinatra in Palm Springs, CA, due to recent revelations of Sinatra's longtime ties to various Mafia crime bosses, instead stayed with Bing Crosby--Sinatra's original rival and an active Republican.
- Von Ryan's Express (1965), was his most successful film of the 1960s, grossing over $17 million (US) in 1965.
- He died in the same month as Phil Hartman, who often impersonated him on Saturday Night Live (1975).
- He was a big supporter of racial equality and the civil-rights movement, at a time where segregation was still a very real and dominant presence in the US. He performed numerous concerts to support activists like Martin Luther King.
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