Frank Sinatra captivated the world through music, movies & sheer magnetism

Frank Sinatra's career and life story at Click Americana

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For decades, Frank Sinatra seemed to be the patron saint of show business, reigning over an impressive kingdom of music, movies, television — and even a bit of politics.

Hailing from Hoboken, New Jersey, Sinatra began his journey to stardom as a skinny kid with big dreams… and oh boy, did he succeed.

Classic classy Frank Sinatra with a cup of coffee

First appearing on the music scene in the late 1930s, Sinatra sang his way into people’s hearts. His voice was more than skillful — it powerfully conveyed universal human emotions, and was a compelling blend of robust strength and tender vulnerability.

It wasn’t all about the singing, though. Sinatra had a certain charisma. From the flick of his fedora to the way he held the microphone, every move oozed charm.

This very magnetism led him to become a formidable figure in Hollywood, starring in over 60 films, and even winning him an Academy Award for Best Supporting Actor in From Here to Eternity.

Everybody loves Frankie as Johnny Concho (1956)

Sinatra was often depicted as the epitome of cool, but he also had his share of rough edges. His relationships were, shall we say, complex tapestries woven with the threads of love, betrayal, and reconciliation. His infamous connection with the underworld often made headlines, turning him into a tantalizingly controversial figure.

And who can forget about the Rat Pack? Sinatra, along with his talented pals — Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop — created a brand of entertainment that was filled to the brim with charm, talent, and unforgettable moments. To say they were the life of the party would be an understatement.

Sammy Davis Jr with Frank Sinatra (1958)

Despite the tumultuous waves of his personal life, Sinatra’s professional journey was a triumphant one. His music, a cocktail of jazz, swing, and traditional pop, reinvented the concept of popular music. His timeless hits like “My Way,” “Fly Me to the Moon,” and “Strangers in the Night” continue to serenade the ears of listeners, both old and young, proving that good music never fades.

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With his rich legacy, Sinatra continues to be an inspirational figure for aspiring artists worldwide. A powerhouse of talent, charisma, and determination, “Frankie” was not just an entertainer, he was a phenomenon. But more than that, he was an artist who understood the human heart, and its longing for a tune that feels like home.

How Frank Sinatra became America’s singing heartthrob (1943)

By Jerry Franken in the Des Moines Register (Iowa) October 17, 1943

One night last February, during Frank Sinatra’s engagement at the Riobomba nightclub in New York, a bizarre and significant event took place.

Sinatra had finished his act — he had just sung “Night and Day” — and was walking off the floor when a woman sitting at a ringside table left her escort, ran after the singer and asked him for his autograph.

Young Frankie ( around the early 1940s)

As he nodded assent and reached for his pen, the woman, obviously prepared and seemingly sober, zipped down the bodice of her dress. “Write it here,” she said, indicating her brassiere.

Although Sinatra politely said no and walked away, the episode marked Sinatra’s emergence into full stature as an American heartbreaker, on a par with the late Rudolph Valentino and with Rudy Vallee when Rudy was at his peak.

1940s Frank Sinatra with Gene Kelly

The effect Sinatra has on women is incredible and cataclysmic. Not since Valentino’s funeral have the women of America so willingly, so hysterically, so publicly fallen in love with one man.

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The most dramatic demonstration of Frank’s devastating hold on females of all ages was furnished in the four-week run at the Paramount Theater. His salary was $2,500 a week, but business was so good that a grateful management gave him a bonus of $1,000 weekly. One typically ardent Sinatra fan, a high school girl, confessed to having seen the show 34 times in four weeks, representing more than one full week’s cut of school classes.

Suave Frank Sinatra with a bow tie (1943)

The outward manifestations of the feminine reaction to Sinatra are given at every Sinatra recital. As he walks out on the stage, he is greeted by applause, screams, whistles, hoots, whimpers, sighs, and a not-too-gentle lowing.

Before he starts singing, Sinatra studies the audience, waiting for the unrestrained joy to subside. As his small voice croons through the microphone, his rapt fans are silent, except for occasional outbursts of heartfelt sighing.

With music arranger Alex Stordahl (40s)

Sinatra is an astute showman. He sings as much with his head, his eyes, and his hands as he does with his voice. He cocks his head to one side, looks softly dewy-eyed — no small trick with a bright spotlight shining into his face — and punctuates the more poignant lines of his corny lyrics by spreading his arms wide and wearing a dewy bovine expression which his followers interpret as one of great emotion. As he breathes the last notes, pandemonium breaks loose.

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Fans follow Frank everywhere

Not content with seeing him on the stage, Sinatra’s fans pursue him everywhere. They trail him to his hotel, the Astor, to his barber, his manager’s office, and to his home in Hasbrouck Heights. They steal his handkerchiefs, yank and saw at his tie, cut swatches from his jacket.

If the crush permits, he signs autographs; when it doesn’t, fans seize his hand, press it on an ink pad, and impress his handprint on other autograph books.

40s fans freaking out about Frankie

While the younger Sinatra fans are by far the least inhibited and the most exhibitionistic, Frank’s hold on other women seems equally secure. Of the 2,500 to 3,000 fan letters he receives weekly, at least half, judging from the handwriting, come from women long past their teens.

All of this adulation, while burdensome and demanding, pays off handsomely. In the first six months of the year, Sinatra earned between $40,000 and $50,000. He’s not quite sure just how much. But whatever the amount is, it’s just a sip of what the gravy train has in store for him in the future.

Young Frank Sinatra (1940s)

A New Jersey childhood

Frank Sinatra was born in unromantic Hoboken, New Jersey, on December 12, 1915. He is the only child of Martin and Natalie Sinatra. His parents were born in America, his grandparents in Italy. Pop Sinatra is a member of Hoboken’s fire force.

Frank’s boyhood was marked by no out-of-the-ordinary events except that he did more than the usual amount of street fighting. He’s not belligerent, but even today, he still gets into a good share of scraps. His Hoboken boyhood put him in touch with all kinds of people, and he is neither a snob nor a discriminator.

Although he is slight and weighs only 130, Frank handles himself well, partly as a heritage from his Hoboken street fights and partly because he has trained. He likes to box and used to work out in a gym at home.

Frank with boxer Tami Mauriello (1944)

It was while Frank was attending Hoboken’s Demarest High School that he first felt like singing. He liked popular music and wangled himself the job of booking bands for school proms. This meant he could get on the stand and sing whenever he wanted to, which was quite often.

He forgot about singing after he graduated in 1936 and went to work for the Jersey Journal, first as a copy boy, then as a helper on a delivery truck, and finally as a cub in sports. Meanwhile, he had become engaged to a Hoboken girl named Nancy Barbato.

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Frank’s big break

One fateful night, he took her to hear Bing Crosby at a Jersey City vaudeville house. Bing’s singing inspired Frank to give up journalism and start looking for singing jobs.

Singers Frank Sinatra and Bing Crosby in the 40s
Singers Frank Sinatra and Bing Crosby in the 40s

Nothing much happened until 1937, when he appeared on a Major Bowes’ amateur program with a quartet called the Hoboken Four. They won first prize and were booked for a vaudeville unit. This lasted six months.

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Back in Jersey after a cross-country tour, he sold himself to five New York stations and sang on some 18 programs a week, starting at 7 in the morning. The only station that “paid” him was WOR, which allowed him 70 cents for carfare. He quit radio for a $15-a-week job as headwaiter and singer in a Jersey roadhouse.

When he got a raise to $25 a week, he and Nancy Barbato were married. That was on February 4, 1939. Frank sang at the roadhouse for five months, and nothing big happened, so in July 1939, he gave notice.

Frank Sinatra in the 1930s with Tommy Dorsey's Pied Pipers

Two days before he was to leave, a musician called and asked if he wanted a job as a vocalist with his band. The musician was Harry James, who was just then leaving Benny Goodman to branch out on his own.

Frank sang for James for six months at $75 a week. When Tommy Dorsey offered him $150 weekly, James gave Frank his release gladly, even though their contract had six months to run.

Frank Sinatra with Bill Henri's band in 1938

James knew that Dorsey’s band was then, and still is, one of the most popular in the country. He knew that Sinatra could go places with Dorsey. As the Dorsey band toured the country and played on the air, swing fans got to know Sinatra’s name.

Young Frank Sinatra as Tommy Dorsey's vocalist

Time right to go it alone

Just a year ago, purely on a hunch, Sinatra told Tommy he wanted to go it alone. “I don’t know why, but I felt the time was right. Something told me. I can’t explain it,” Frankie said. “I did feel that I had gone as far with the band as I ever could. So I blew.”

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People who try to account for Sinatra’s overnight success frequently attribute too much to his publicity build-up. Actually, the publicity came afterward.

Sinatra himself credits his success to a combination of circumstances, the most fortuitous of which was that he left Dorsey at just the right moment to get a five-time-a-week sustaining program of his own on the Columbia Broadcasting System, with an audience of millions. This led to his contract with Lucky Strike and Riobomba bookings.

Young Frankie in a chair that said THE VOICE

In one respect, Sinatra differs from idols who have preceded him. Men don’t resent him the way they did Valentino and Vallee. Soldiers stationed in all parts of the world send him tokens. He has a good collection of campaign ribbons.

One, a yellow pre-Pearl Harbor ribbon with a bronze star, was mailed at the request, so the story goes, of a dying marine. This sort of allegiance explains why he is one of the performers who make records regularly to be sent by the office of war information to servicemen abroad.

Sinatra on the cover of Modern Screen magazine (1944)

Although he has never formally studied music, can’t play an instrument, and can’t read music, Sinatra nevertheless maintains that he knows music and the art of singing, certainly as it applies to himself. He thinks he’s a good singer, not in the Crosby class, as his friends persist, but a guy who knows what he wants to do with a song and how to do it.

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His technique

He credits his singing technique to two major influences, the trombone playing of Tommy Dorsey and the trumpeting of Ziggy Elman, one of the greatest swingsters of the day, who’s had his own band and has starred with both Benny Goodman and Dorsey.

From Dorsey, generally recognized as one of the finest “slush pumpers,” Sinatra says he learned the art of “sliding” his notes. “I sort of ‘bend’ my notes,” he says. “gliding from one to another without abrupt breaks. The trombone is a great example of that.”

Frank Sinatra on TV in the 50s

By studying Elman’s trumpet technique, Frank learned to inject a slight quaver into his phrasing, similar to the technique used by cantors. That sort of wail or quaver, Sinatra says, gives his song a plaintive quality. It adds to the emotional sincerity of his singing.

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No popular singer ever got anywhere without convincing his listeners that he really believed the sentiments that he was mouthing. Proof that Frank’s style convinces his audience may be observed at any performance. When, for instance, he does George Gershwin’s “Embraceable You,” opening his arms wide and crooning, “Come to papa, come to papa, do,” the audience hollers, “Oh, daddy!”

Vintage 50s portrait of Frank Sinatra (1957)

“That’s a lot of kids for one fellow,” he says softly into the microphone and goes on singing. I asked Sinatra about critics who maintain he’s usually a half note or so off key. “Nuts,” he said. “If they knew music, or at least knew enough to realize what I’m doing when I sing, they’d never say it. Those characters just don’t know.”

Since quitting Dorsey, for whom he sang both ballads and rhythm songs, Sinatra has done only ballads. His voice is small, and he thinks it’s best adapted to a slower tempo; he’s not afraid that this unvaried diet will tire his listeners.

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Suits and bow ties

Sinatra today is a healthy, tanned specimen. He has blue eyes and brown hair, which looks as though it were carefully and studiously tousled.

His clothes — made by a Hoboken tailor, De Sento — make him look bigger and broader than he is. He is 5 feet 10. He pays $75 for a suit and $40 for a sports jacket. His singing of the last year has increased his neck size from 14 to 15. He favors bow ties.

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Frank Sinatra's first wife Nancy with one of their babies (1940s)

In manner, Sinatra is quiet but cocky and supremely self-confident. As much as his calling allows him to be, Frank is a home man. Before he reached stardom, he spent his spare time tinkering around his house or at sports. His home in New Jersey has a practice golf range, a makeshift gym, a badminton court, and an archery range.

1940s Sinatra with daughter Nancy and wife Nancy

He seldom goes home without a trinket for his wife, Nancy, and their daughter, also Nancy. Mrs Sinatra keeps house and does the cooking, a maid coming in two or three times a week. The Sinatras expect a second child. Frank says December.

DON’T MISS: See his daughter Nancy singing her hit “These Boots Are Made For Walkin'”

1950s Sinatra with kids Frank Jr and Nancy (1957)

About three years ago, Sinatra went long-hair, musically, and began acquiring a collection of recorded classics. He goes for Debussy, Wagner, and Sibelius and says he has “just got to savvy Wagner.” His desire to know the classics is not purely cultural. He hopes to learn from them and see what made the famous composers tick.

The one fear of Frank’s is that something will happen to his voice. At least several times a month, he goes to the same throat specialist who treats Kate Smith and many other singers, paying $10 a visit.

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How high school girls feel about Frank

What high school girls think about Sinatra is symbolized in this quotation from a follower as she waited in a long line outside New York’s Paramount Theater to get in to hear her idol: “When I hear him I don’t know what struck me. I look at him and my heart stops.

“He’s the only man that ever thrilled me. I get goose pimples all over. Then when he starts singing, I feel suddenly cold. I feel small. To me, it’s like he’s the only one living in this world — singing, singing.

From the movie Anchors Aweigh (1945)
With Gene Kelly and Dean Stockwell in the movie Anchors Aweigh (1945)

“My hands get sweaty. I bite my nails, and I grab ahold of my girlfriend’s arm and squeeze it tight. I do the same when I’m with a boy. I feel more romantic with the boy I’m with. They like it when they’re with me and I hear Frank Sinatra. When he sings ‘Night and Day,’ ooh, that really gets me. I could listen to him singing that forever.

“How lucky. No, I never talked to him, but I always wanted to meet his wife — to tell her how lucky she is. Every Saturday night, I and my friends listen to Frank Sinatra on the radio. Honest, he just swoons me. What a swooner he is. It’s hard putting into words. I feel like — like kissing him.”

Youg singer Frank Sinatra head shot (c1940s)

Sinatra at 50 aims for more fun and money

By James Bacon in the Charlotte Observer (North Carolina) December 12, 1965

The daughters of the teen-aged girls who used to swoon over Frank Sinatra have long since turned to the Presleys and the Beatles. But the indestructible Sinatra goes on and on. Just now turning 50, the youthful idol of 25 years ago is making more money and having as much fun as ever before.

Frank Sinatra through the years (until 1975)

HOLLYWOOD — Frank Sinatra hits 50 today, still making money and whoopee — and as ready as the rich sybarite that he is to make more of both.

“I look upon it as the halfway mark,” says the skinny one from Hoboken, NJ, who has been called the top pop vocalist of his time. “I expect to swing for 50 more. You only live once, and the way I live, once is enough. I stole that from Joe E Lewis, who is Dean Martin’s drinking coach.”

Dean Martin, opera star Robert Merril and Frank Sinatra on Sinatra and Friends (1970s)

Coincidentally, it’s also the 25th anniversary of Sinatra’s career as a recording star. The industry calls him the top album seller of all time. He estimates his records have grossed $100 million. Even albums recorded more than a decade ago net him $60,000 a year.

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“Sinatra is so rich he even hires Crosby,” cracks comedian Bob Hope. There is as much truth as humor to the remark. Bing, his greatest rival as a crooner, now records on Frank’s Reprise label.

Sinatra single Stay With Me and Talk To Me Baby (1964)

And, true to his reputation as a sharp businessman, Sinatra is using the occasion of his 50th birthday to rake in a little stray cash. His newest album, which probably will be another bestseller, is called “September Of My Years.”

The Sinatra birthday celebration will be mostly a family affair, hosted by his first wife, Nancy, and the couple’s three children. Frank, Jr., may not be able to make it. He’s on the road band-singing just as his father did 25 years ago.

Frank with late night talk show host Johnny Carson on the Tonight Show (1970s)

“As I look back, I consider myself an overprivileged adult who had a lot of help from a lot of wonderful people along the way — especially from the public who still buy my albums out there in Beatle-land.

“For the future, I’ll go on pretty much as I have in the past. I may direct more pictures and produce others, but I’ll act too. And, of course, I’ll play the saloons. There’s nothing like that live audience to keep your pipes in tune.”

Young Sinatra in 1943 and at age 50 in 1965

Sinatra is now a giant in Hollywood. A favorable nod from Sinatra can zoom a career. But the road to success out of Hoboken wasn’t an easy walk. Sinatra says sometimes he acts as if he hasn’t been an unhappy man possessed. His moods are varied as his songs. When he’s charming, Cary Grant couldn’t take lessons from him. When he isn’t, watch out!

Interviewing comedy legend George Burns - guest host on the Johnny Carson show (1970s)
Interviewing comedy legend George Burns – guest host on the Johnny Carson show (1970s)

To his credit, nowadays he is charming much more than he is belligerent. “I have a Sicilian temper,” he explains, “but over the years, I have admired people with restraint. I guess I’ve wanted to be more like them. I feel I’ve mellowed.”

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Frank is never alone. Chicago can be a very lonely town — unless you want every night to be New Year’s Eve. Frank drinks. Frank swings. Yet, he finds time to run a huge enterprise with a business acumen that would do justice to a Wall Street banker.

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Sinatra single The World We Knew (1967)

As a musician, he can’t read a note, but he is an uncanny editor of music. He knows what is best for him. When he sings a new song, it is tailor-made for him.

Jimmy Van Heusen and Sammy Cahn, two of Frank’s favorite songmakers, admit that they write for the Sinatra style. “Even if Frank doesn’t like it, there are so many Sinatra imitators that the song is bound to be a hit,” says Cahn.

Recording session at Reprise with Frank Sinatra, Bing Crosby, Sammy Davis and Dean Martin (1965)

Sinatra’s first big hand job was with Harry James in 1939. Then came the famous early war years with Tommy Dorsey. Bobby Burns, Dorsey’s band manager, watching women melt at Sinatra’s singing, figured it was time for Sinatra to go on his own — and the big publicity buildup began.

Recalls Jack Keller, one of the publicists: “We outfitted Frank with breakaway suits and hired girls to scream when he sexily rolled a note, but we needn’t have. What happened was a lot more than even a press agent had envisioned. This was early in the war years, and a lot of girls were without men — and romance. The girls we hired to scream swooned, and hundreds more we didn’t hire swooned with them.”

Frank Sinatra and Lana Turner (1944)

The Ed Sullivan Show was a launchpad for legends (1948-1971)

A punctured eardrum made Frank 4-F in the draft, and he became the stay-at-home romantic idol of girls pining for their boyfriends overseas. The fact that he had married his high school sweetheart, Nancy Barbato, and had fathered three children by her made no difference in his appeal to the bobby-sox set.

He married Nancy in 1939. They were divorced in 1951. They are still the best of friends, and Nancy is included in many of Frank’s parties. Says the attractive ex-wife: “No father could be more devoted or kinder to his family than Frank. And no family could love their father more.”

Frank Sinatra with granddaughter on cover of Ladies' Home Journal magazine (1974)
Frank Sinatra with granddaughter on cover of Ladies’ Home Journal magazine (1974)

Frank is also on good terms with his other ex-wife, Ava Gardner. The two had a stormy romance, a stormier marriage. But whenever Ava needs help, be it in Spain or in town, Frank is the first person to get a phone call.

Frank Sinatra with Ava Gardner (1952)

Close friends believe he will marry Mia Farrow, the 20-year-old daughter of actress Maureen O’Sullivan and the late director, John Farrow. “But only,” says one buddy, “if she gives up her career to be Frank’s wife.”

Juliet Prowse got as far as the engagement ring, but chose career over Frank. No wedding ring.

Sinatra's love life - a look back from 1965

The low point in Sinatra’s career came during his marriage to Miss Gardner. Heartthrob singing idols no longer sang to lonely women, because the GIs were home and the girls weren’t lonely anymore. In his last years with Columbia Records, his average single sales dipped to 30,000 a record — hardly enough to pay the band. Columbia dropped him, his agents dropped him, and his studio dropped him.

When his career seemed at an end, Sinatra sought and got the role of Maggio in “From Here to Eternity” — receiving only $750 a week for eight weeks. It also won him the Academy Award for the year’s best actor in support. It catapulted him into tycoon status among stars.

From Here to Eternity movie (1953)

No one knows for sure what Frank grosses a year, and he isn’t saying. One business associate who should know puts it between $1 and $5 million a year, depending on the box office returns of his movies, which usually gross well.

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He has a big office-bungalow at Warner Bros., which Jack L. Warner built just to entice Frank’s production company. The red carpet treatment has led to speculation that Sinatra is the heir-apparent to Warner’s throne when the latter retires.

Frank with Ella Fitzgerald and Count Basie in the 70s

Some of Sinatra’s temper tantrums have occurred after he has enjoyed liquid refreshments. But sometimes he gets mad when he’s sober.

“I can’t stand people grabbing on my arm,” he moans. And since he is a giant in the industry, a lot of people grab on his arm.

There has been much controversy over the years about Sinatra’s personal behavior and his friendships. But one thing uncontroversial about Frank is his singing. Most everybody agrees on that.

Frank Sinatra concert audience at Madison Square Garden in New York City (1978)

Crosby recently paid him a rare compliment. “I’m a crooner. Frank is a singer, and a much better one than I. He’s certainly the greatest of our time, and probably the greatest entertainer, too.”

Then, as a tag line, the Ol’ Groaner adds: “He’s the type of singer who comes once in a lifetime, but why did he have to come in my lifetime?”

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See Ol’ Blue Eyes, Frank Sinatra, through the years

Baby Francis in 1916

Baby Frank Sinatra

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2-year-old Frank Sinatra and his mother on a boat trip off the Jersey shore (c1918)

2-year-old Frank Sinatra and his mother on a boat trip off the Jersey shore (c1918)

As an adult with his mom, Natalina (Dolly) Sinatra

Frank and his mom, Natalie Sinatra

Antique portrait of toddler Frank Sinatra at age 3

Antique portrait of toddler Frank Sinatra at age 3

Young Frank Sinatra as a child (around age 12)

Young Frank Sinatra as a child about 12 years old

Teenage Frank Sinatra photo

Teenage Frank Sinatra photo

Vintage Frank Sinatra mirror selfie from 1938

Vintage Frank Sinatra mirror selfie from 1938

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Frank Sinatra with his first wife and their family (c1950)

Frank and his family around 1950

Frank Sinatra with his two oldest kids (1954)

Frank Sinatra with his two oldest kids (1954)

Frank & second wife Ava Gardner at the theatre (1950s)

Frank Sinatra and Ava Gardner at the theatre in the 50s

Frank’s wedding to 3rd wife, actress Mia Farrow (1966)

When Frank Sinatra and Mia Farrow got married (1966)

Frank with wife Barbara Sinatra (1970s)

Barbara was his fourth and final wife, who was with him until he died. It was her third marriage — and her second husband was Zeppo Marx of the Marx Brothers.

Frank with wife Barbara Sinatra

Frank singing onstage in the late 70s

Frank singing onstage in the late 70s

As the highlight of Chicagofest on August 10, 1982
Sinatra in 1982
(Photo by Laurence Agron/

He did it his way (1915-1998)

The legendary Frank — who had been born Francis Albert Sinatra — died on May 14, 1998, at age 82.

Frank Sinatra's gravesite - headstone in California (1915-1998)
Sinatra’s original gravesite/headstone at Desert Memorial Park, Cathedral City, CA (Danielschreurs/Dreamstime)

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