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The Best of Frank Sinatra

Updated on May 22, 2012

What can you say about a legend, a classic? Someone who defined the music industry and still remains unforgotten, even more than a decade after his death?

Frank Sinatra has become more than an icon. His music is still loved and sells by the millions. Highly successful modern artists have built whole careers on his songs, imitating the inimitable style that only he could ever fully possess. The smooth voice, the effortless charm, the blue eyes and boyish grin are all part of his aura. Frank Sinatra has become a genre to himself, and here are ten of his best, most famous, and loved songs ever recorded.

The Way You Look Tonight

This song has become a standard recorded by many artists of every style in pop, jazz, or just about any other genre you could think of. Frank's recording has an upbeat, casual swing that makes it likeable, listenable and always a favorite. It was first heard sung by Fred Astaire in the 1936 film Swing Time and won an Academy Award for Best Original Song that year but it wasn't recorded by Sinatra until 1964. He created a standard by which many have since made their own recording.

Come Fly With Me

Written by Sammy Cahn and Jimmy Van Heusen specifically for Frank Sinatra, Come Fly With Me became a Sinatra standard. After using it as the title number of a 1958 album it was such a hit that it became a standard part of his concert repertoire. There was even a movie made by the same name in 1963 that featured Frankie Avalon singing the theme song, and more recent artists have brought back it's popularity.

The Lady is a Tramp

Witty and sarcastic, mocking and funny, The Lady is a Tramp has been a large part of many artist's repertoires. Sinatra sang it in the film Pal Joey and often during his career, and in 1968 Sammy Cahn rewrote the lyrics for Frank to record a special version for he Beatles. The master recording and all duplicates were destroyed, making the single surviving recording is quite possibly one of the most valuable records in the world.

My Way

It's the song most often identified with Frank Sinatra's persona, but he himself disliked it, calling it "self-serving and indulgent." But if any man ever truly did it his way it was Frank Sinatra, whether it was working his way up through the musical industry from a very humble beginning in Hoboken, New Jersey, or coming back from a vocal hemorrhage that should have ended his singing career forever. The tune is based on a French song and Paul Anka wrote the lyrics with Sinatra in mind and though it's considered one the most covered songs in history it will be forever linked to the image of Sinatra.

Somethin' Stupid

One of the many duets Sinatra recorded includes the hit Somethin' Stupid with his daughter Nancy. The original recoding in 1967 shot to the top of charts and stayed there for a long time, eventually selling over a million copies and becoming one of Sinatra's biggest hits.

Fly Me To The Moon

Originally title In Other Words, the song was made popular in cabarets in the early 50s with a waltz rhythm, but was arranged by Count Basie for Sinatra in the now-traditional 4/4 swing. Astronauts on Apollo 10 played his 1964 recording while in lunar orbit and again on the moon as Buzz Aldrich was landing in Apollo 11.

Night and Day

It's slow and romantic, with a smooth jazz background to support Frank's silky voice. Cole Porter claimed that the song was inspired by an Islamic call to worship while he was traveling in Morocco and especially the opening has a Middle-Eastern sound to it. Sinatra first recorded in in 1942 but went on to record it at least four more times during his career with the most unique being a disco version from 1977. Even Frank Sinatra had to keep up with musical trends.

You Make Me Feel So Young

The upbeat tune and catchy lyrics make this song a definite sing-along. Who can help but swing along with "You and I/Are just like a couple of tots/Runnin' across the meadow/Pickin' up lots of forget-me-nots!" Perfect for people of any age who find themselves in love.

Don't you wish you knew what he was singing right there?
Don't you wish you knew what he was singing right there?


A love song that joyfully delights in the prospects of a happy marriage and a lifetime of bliss to ensue. Like Come Fly With Me, Ring-a-ding-ding! was written for Sinatra by Cahn and Van Huesen as the title number of a 1961 album of upbeat swing numbers. The record was on best selling charts in the U.S. for 35 weeks, and in Europe for nine weeks. Talk about a show-stopper!

As Time Goes By

The beautiful, haunting song most famous from the 1942film Casablanca never sounded so wistful and longing as when Frank gives it an interpretation. Originally from a 1931 Broadway play called Everybody's Welcome, As Time Goes By was given it's best remembered rendition by Dooley Wilson in the film. But Sinatra's is an unusually tender and vulnerable rendition for him, showing a side to his talent that all of the upbeat swing could never reveal.

These songs are some of Sinatra's most famous, but they are also the ones that I love best. I hope you enjoyed the list and take a minute to share some of your own favorites with me. Cheers to Old Blue Eyes, who gave us nothing but the best.

Which of These Songs is Your Favorite?

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    • Kenja profile image

      Ken Taub 

      5 years ago from Long Island, NY

      Very reassuring to see someone pay homage to Sinatra in 2012. I think his songbook and his voice will still be appreciated 100 years from now, probably longer. The great ones hold up. Nice.

    • collegatariat profile imageAUTHOR


      6 years ago

      Thank you so much for your kind comment epigramman, and I appreciate your sharing it on Facebook! I would love to join your group-- I found it and have sent a request to join.

      I didn't know that about Frank giving the wrong song credit for the song Something-- just proves that even the best of us can make mistakes. ;) It's always fun to realize that no matter how much you know about someone, there's always something to learn from others. Thank you for stopping by!

    • epigramman profile image


      6 years ago

      I can't believe no one has left a comment here - shame on the so called hip hub crowd because this is truly a labor of love and everyone's dream of what a music tribute should look like -needless to say I love Frank in all of the stages in his career and songs like That's Life, It was a very good year and his sessions with Jobim and even singing Harrison's Something in which Frank credited it to Lennon/McCartney - lol - I will post this marvel to my FB music cinema group with a direct link back here and will invite you to the group if you are so inclined - there is lots of classical music too and everything else - the group is called Let's just talk music or cinema and I am sending you warm wishes and good energy from lake erie time ontario canada 2:09am


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