Raise A Glass for Crooner Frank Sinatra on the Anniversary of His Death

frank sinatra
Everett Collection

The “Chairman of the Board” and New Jersey Native, Frank Sinatra, was not only a charmer with the ladies, but he was also a double threat when it came to his acting abilities (he won an Oscar for his performance in From Here to Eternity) and singing (11 Grammy awards). In honor of the 26th anniversary of his passing on May 14th, 1998, let’s take a look back at some of his most iconic songs and movies.

Sinatra’s Best Known Movie Roles

Guys And Dolls

GUYS AND DOLLS, Marlon Brando, Jean Simmons, Frank Sinatra, Vivian Blaine, 1955

Courtesy Everett Collection

Since Sinatra could both sing and act, it makes sense that he was featured in several musical films. One of these was the 1955 film Guys and Dolls, where Sinatra played a gambler opposite Marlon Brando. Sinatra actually didn’t really like this film but the audience loved it and made it one of his classics.

Choreographer Michael Kidd, Johnny Silver, Frank Sinatra, Stubby Kaye, in rehearsal, 1955
GUYS AND DOLLS, choreographer Michael Kidd, Johnny Silver, Frank Sinatra, Stubby Kaye, in rehearsal, 1955

Courtesy Everett Collection

High Society

HIGH SOCIETY, from left: Bing Crosby, Grace Kelly, Frank Sinatra, 1956

Everett Collection

A year later, Sinatra starred in another musical in 1956’s High Society with Bing Crosby and Grace Kelly. It is actually a musical adaptation of the 1940 film The Philadelphia Story. Sinatra plays a tabloid reporter that is tasked to cover the upcoming wedding of Tracy Lord and George Kittrredge. This was Kelly’s last film before her retirement from acting. You can’t miss Crosby and Sinatra’s duet “Well, Did You Evah.”

From left: director Charles Walters, Bing Crosby, Grace Kelly, Frank Sinatra, producer Sol C. Siegel on set, 1956
HIGH SOCIETY, from left: director Charles Walters, Bing Crosby, Grace Kelly, Frank Sinatra, producer Sol C. Siegel on set, 1956

Courtesy Everett Collection

Pal Joey

PAL JOEY, Rita Hayworth, Frank Sinatra, Kim Novak, 1957

Courtesy Everett Collection

Pal Joey (1957) showcases Sinatra’s acting chops as a womanizer named Joey Evans and also stars the beautiful Rita Hayworth. The movie focuses on how Joey meets a sweet girl named Linda, played by Kim Novak, who is too smart for his usual boyish charms, and how he eventually wins her over and changes his ways.

Frank Sinatra on set of Pal Joey, 1957
PAL JOEY, Frank Sinatra on set, 1957

Courtesy Everett Collection

 

The Manchurian Candidate

THE MANCHURIAN CANDIDATE, Frank Sinatra, 1962

Everett Collection

1962’s The Manchurian Candidate was definitely different than his usual musicals. It was a political thriller that is often considered one of his best onscreen performances, based on the novel by Richard Condon. Sinatra plays Major Bennett Marco, an Army veteran of the Korean War. Sinatra was reportedly very excited about a different kind of role and showed that he could do it all.

Frank Sinatra and John Frankenheimer (director) on the set of The Manchurian Candidate , 1962
Frank Sinatra and John Frankenheimer (director) on the set of THE MANCHURIAN CANDIDATE, 1962

Courtesy Everett Collection

Oceans 11

OCEAN'S ELEVEN, (aka OCEAN'S 11), from left, Frank Sinatra, Sammy Davis, Jr., Dean Martin, Peter Lawford, Joey Bishop, 1960

Courtesy Everett Collection

The entire Rat Pack including Sinatra, Dean Martin, Sammy Davis Jr. (the anniversary of his death is coming up on May 16th), Joey Bishop, and Peter Lawford starred in Ocean’s Eleven (1960). Shirley MacLaine also makes an unscripted appearance, reportedly because she just wanted to hang out with her Rat Pack friends. Sinatra stars as Danny Ocean who recruits his old Army friends to pull off the heist of the century. The movie was so popular that it spawned a remake in 2001.

Dean Martin, Sammy Davis Jr., Danny Thomas, Lucille Ball, Frank Sinatra stand around a cake for the eleventh anniversary of the Sands Hotel in Las Vegas. On the extreme left is Sands President Jack Entratter
Dean Martin, Sammy Davis Jr., Danny Thomas, Lucille Ball, Frank Sinatra stand around a cake for the eleventh anniversary of the Sands Hotel in Las Vegas. On the extreme left is Sands President Jack Entratter

Bettmann/Getty

 

No ‘Witchcraft’ needed for his singing career

Ol’ Blue Eyes got his start singing as a teenager in the 1930s and growing his voice in the big band era. Throughout his long career, he had many hit songs and is one of the top-selling musicians worldwide. Let’s look back at some of our favs.

Perhaps one of the most covered Sinatra songs, “Come Fly With Me” is about a musical trip around the world and was his first collaboration with arranger Billy May. It is one of those perfect Sinatra songs that are so easy to sing and just puts you in a good mood.

“Love and Marriage” is a bop that many know as the theme song from the show Married… With Children.

Sinatra certainly had a lot of love songs and inspired countless romances over the years. “The Way You Look Tonight” is one of those that is perfectly jazzy and a beautiful way to say “I love you” to that special someone. It is one of the most popular wedding songs of all time.

The ’50s brought “I’ve Got The World on a String” which is a perfect example of an out-of-tempo introduction before the big band sound kicks in.

“Fly Me to the Moon” and “New York, New York” might be tied for the most iconic Sinatra songs.

The first was originally titled “In Other Words” and meant to be a waltz. However, it was repurposed by arranger Quincy Jones who gave us the song we know and love today. The latter is a love letter to New York City and became one of his signature songs. It was originally written for Liza Minnelli to perform in a film of the same name.

Lastly, “The Best is Yet to Come” was released by Sinatra in 1964 and became the last song that he ever performed in public. The title lyric is on his gravestone located in California. What is your favorite Sinatra song? Favorite film? There are so many classics that it was hard to narrow it down for this list!

Frank with his fourth and longest wife, Barbara Sinatra, in 1990
LOS ANGELES - 1990: Singer Frank Sinatra and Barbara Sinatra pose for a portrait in 1990 in Los Angeles, California

Harry Langdon/Getty Images

 

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