Frank Sinatra’s Mystique Stands the Test of Time

Singers and entertainers come and go all the time, but rarely will you run across one with the same mystique as Frank Sinatra.

Just think for a minute about his career. Nightclubs, concerts, radio shows, and television shows allowed Sinatra a chance to showcase his immense talents. You can’t talk about him without mentioning “The Rat Pack,” made up of Sinatra, Sammy Davis Jr., Dean Martin, and a few others.

It seemed like “The Chairman of the Board” always had the best producers and musicians around. Recording sessions were usually held at night. That was the time he felt more alive for making his records. Frank Sinatra wasn’t always the nicest guy to be around. He could be testy, tough, and aware of his enemies.

Still, what is it about his mystique? Generations grow up hearing songs like My Way, Nice and Easy, The Girl from Ipanema, Strangers In The Night, Fly Me to the Moon, and hundreds more. His romantic life has been written about over time. Women, Jack Daniels, and a good time played big roles in many Frank Sinatra stories. It’s been mentioned over the years that Sinatra could be abusive with his female companionship.

Keeping Trusted People Close By Mattered To Him

Frank Sinatra, Chairman of the Board, Ol' Blue Eyes, Jilly Rizzo, 1960s Songs, 1970s Songs

Of course, Sinatra surrounded himself with people he trusted. There was no other close confidant than Jilly Rizzo, who oversaw Jilly’s Saloon in New York City. It was a place Sinatra frequented often. After leaving the saloon business, Rizzo became even closer with Frank Sinatra. Rizzo was killed by a drunk driver in 1992, sending Sinatra into seclusion.

Trust was a big issue for Sinatra. If you weren’t one of Frank’s close friends or entertainment buddies, then you might be out of luck. He didn’t always open up with everyone. Fans can go out on YouTube and see a few interviews Frank Sinatra did while alive.

One of the better ones is his interview with famed CBS newsman Edward R. Murrow. In this one, Sinatra looks relaxed and engaging. He’s not holding back from Murrow or his viewers. Sinatra had a toughness about him, probably from his youth.

Tough and arrogant at times, he also could be soft and kind. There have been stories shared over the years about Sinatra’s heart of charity. Nancy Sinatra, one of Frank’s daughters, sat behind a microphone for her weekly show Nancy for Frank on SiriusXM. She especially shared with fans so many magnificent stories about her father. In doing so, the Frank Sinatra mystique grew and grew.

Let’s talk a little more about his music. He started singing in Big Bands led by Tommy Dorsey and Harry James. From there, Sinatra performed in front of screaming fans at places like the Paramount in New York City. He became a “must-see” singer in the 1940s. Radio and the early days of television gave him places to shine.

As Frank Sinatra grew in popularity, so did his music. He would sing songs that were chart toppers at the time. Over time, though, songwriters eventually found their work in Sinatra’s hands. His phrasing, style, and voice became very recognizable.

Frank Sinatra Turned Himself Into a Movie Star

Sinatra picked up work in movies, getting some lead roles where he could sing. Fans who might not have been able to see him live could get an on-screen experience. He added to his mystique with musicals, solid acting roles, and playing a private investigator.

Nevertheless, it was music and live appearances that made Frank Sinatra a fan favorite. His appearances at the Sands Hotel with Count Basie and his Orchestra were legendary. Great music, solid songs, and a little rap with the crowd had their place in his shows.

In 1971, Sinatra surprised many people by retiring from his career. Yet this didn’t last long, and he returned to perform in 1973. In 1974, he got a televised concert titled Sinatra: The Main Event lined up on ABC. This concert was held at a sold-out Madison Square Garden. It allowed millions of people to experience a Sinatra concert in the comfort of their own homes.

Later in-person appearances gave live audiences in the United States and around the world time with “Ol’ Blue Eyes.” But like all entertainers, Frank Sinatra reached the end of his performing road. His ability to perform all of his famed hits slipped away. So, it was time to leave the road. Sinatra, with his band, did one final private concert in 1995. He didn’t stand in front of a band again.

“And now, the end is near…” as the song goes. It sure was for Frank Sinatra, who died of a heart attack in 1998 at 82 years old. Sinatra had many albums to his name, including those in the Duets series. While those recordings allowed Sinatra to share his voice with other musicians, they weren’t like earlier albums.

The Frank Sinatra mystique, though, is alive and well. Fans can tune in 24 hours, seven days a week, to Siriusly Sinatra, his very own SiriusXM channel. You probably have your own Sinatra songs that you hum here and there. It’s not surprising because how can you not love his music? It lives through young and old alike.

You better believe Frank Sinatra still matters to this very day.

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Joe Rutland is an author, writer, and editor whose work has appeared on numerous large-scale digital platforms. Among them are Entrepreneur, The Good Men Project, The Huffington Post, Thrive Global, and Elite Daily. Rutland is on X @JosephRutland5.

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