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5 classic Frank Sinatra moments


Friday, December 11, 2015, 4:11 PM

Joe DiMaggio and Frank Sinatra at Yankee Stadium in 1949.New York Daily News/KRT

Joe DiMaggio and Frank Sinatra at Yankee Stadium in 1949.

He once crooned, “Each time I find myself flat on my face, I pick myself up and get back in the race.”

And Frank Sinatra did just that — relaunching his career after he lost his audience, the movie deals and his second wife, Ava Gardner.

A role in the 1953 film, “From Here to Eternity,” resurrected his career — and began his ascension to one of the most popular entertainers of the 20th century.


Along the way, Sinatra had several defining moments that exposed him as an enigma of a man that included traits of loyalty, generosity, toughness and supreme talent.

Here are a few of the biggest moments of Sinatra’s life:

Consoles Mia Farrow in an unusual way

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Frank Sinatra with his 21-year-old bride Mia Farrow, shown here after their marriage in July, 1966,

Sinatra married Mia Farrow in 1966.

The marriage was short-lived, and ended in divorce less than two years later.

Despite the breakup, they remained close friends for the rest of Sinatra’s life.

It was this friendship that caused his less-than-friendly reaction to Farrow’s public breakup with Woody Allen 1992.

According to Farrow, Sinatra attempted to comfort her after it was revealed that Allen was having an affair with the then-22-year-old daughter she had previously adopted.

His consolation?

Offering to have Allen’s legs broken.

Farrow, who didn’t take Sinatra up on the proposal, testified in a deposition that the offer was “a joke.”

Takes offense to Sinead O’Connor’s anti-Pope stance


Frank Sinatra took offense to Sinead O’Connor’s antics on “Saturday Night Live.”

In October 1992, Irish singer Sinead O’Connor, whose song, “Nothing Compares 2 U,” was an international hit, was hosting “Saturday Night Live.”

In an effort to protest the sexual abuse in the Catholic Church, O’Connor held up a picture of Pope John Paul II and said, “Fight the real enemy,” before tearing up the photo.

But her antics did not sit well with the Chairman of the Board.

At a concert in New Jersey following O’Connor’s stunt, Sinatra went off on the singer.

“This must be one stupid broad,” he said, according to the Tom Santopietro book, “Sinatra in Hollywood.”

“I’d kick her ass if she were a guy. She must beat her kids to stay in shape.”

Busted for “Seduction”

Frank Sinatra was arrested by the Bergen County Sheriff's Department in 1938 for "seduction."

Frank Sinatra was arrested by the Bergen County Sheriff’s Department in 1938 for “seduction.”

Considering the company he often kept — Sinatra was friendly with high-ranking mobsters from New York to Los Angeles — it’s no surprise that the FBI kept an extensive file on the singer.

One of the more interesting notes details his 1938 arrest by authorities in Bergen County, N.J., for “seduction.”

According to the file, “On the second and ninth days of November 1938 at the Borough of Lodi and under the promise of marriage (Sinatra) did then and there have sexual intercourse with the said complainant, who was then and there a single female of good repute.”

After the woman was discovered to be married, the charge was dropped, but Sinatra was then charged with “adultery.”

Shortly after, all charges were dismissed.

Battles Marlon Brando on the “Guys and Dolls” set

Sinatra was known for being an opinionated and passionate man — not the type to feign respect or admiration for someone whom he did not like.

So when he and Marlon Brando were both cast in the film “Guys and Dolls,” there was tension from the outset.

With Brando cast as the romantic lead, Sinatra’s jealousy began to show, according to Turner Classic Movies, with Sinatra refusing to perform the ballad, “Adelaide,” in character.

Instead, he used his romantic charm, which was in contrast to his character, Nathan Detroit.

Brando, whose ego rivaled Sinatra’s, allegedly complained to the director that there could only be one romantic lead.

The hostility continued throughout the shoot, and Brando allegedly declared he would never work with Sinatra again (he never did).

Later, Sinatra told Newsweek, “I wanted to play Masterson. I mean nothing disparaging about Marlon Brando, but Masterson didn’t fit him, and he knew it.”

Speaks out against racial intolerance in 1945

When he heard about white students in Gary, Indiana, walking out of their high school to protest the admission of black students, Sinatra traveled to the school.

He spoke to the students of Froebel High School about bigotry, telling them to “knock it off, kids.”

The boycott ended a short time later.

Some argue that Sinatra’s views on racial equality were a contributing factor to his career taking a dive in the 1940s.


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