3 Legendary Frank Sinatra Songs That Remain as Iconic Today as the Day They Dropped

Known as “The Voice,” Frank Sinatra had a strong grip on the ears of the masses for the vast majority of his life. Born in 1915 in Hoboken, New Jersey, Sinatra crooned his way to the top of American—and, really, global—pop culture. Presidents wanted his influence, men and women all over wanted to be in his audience. (Side note: this video remains incomparable when it comes to the passing of the torch between Sinatra and Elvis Presley as modern icons.)

Of course, along the way during his career, Sinatra released incredibly well-known hit songs, many of which have stood the test of time thanks to his golden voice and nonchalant delivery. Here below, we wanted to explore a trio of such songs that continue to influence the radio waves and minds of listeners around the world. Indeed, these are three eternal Frank Sinatra songs.

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[RELATED: Six Artists You Didn’t Know Covered Frank Sinatra]

“New York, New York” from Trilogy: Past Present Future (1980)

Though he was from New Jersey, New York City was home for Sinatra for some time. And he showed his passion for the region on this track. Originally recorded in 1977 by Liza Minnelli and released for the soundtrack for the Martin Scorsese film of the same name, Sinatra took a stab at the track a few years later and released it for the 1980 triple album Trilogy: Past Present Future. On the song, he sings with love and confidence,

Start spreadin’ the news, I’m leavin’ today

I want to be a part of it

New York, New York

These vagabond shoes, are longing to stray

Right through the very heart of it

New York, New York

I wanna to wake up, in a city that doesn’t sleep

And find I’m king of the hill

Top of the heap

“My Way” from My Way (1969)

Perhaps the quintessential Sinatra song, this track is about living life how you want—your way or the highway, so to speak. The lyrics were written by Paul Anka and set to the music of the unrelated French song “Comme d’habitude.” On the English-language offering from Sinatra, the crooner, reflecting on his years, talks about how his time on Earth came with few regrets. With big swings and lots of success. For a man known for his confidence and his grip on the world, it remains an iconic track. On it, he sings,

And now, the end is near

And so I face the final curtain

My friend, I’ll say it clear

I’ll state my case, of which I’m certain

I’ve lived a life that’s full

I traveled each and every highway

And more, much more than this

I did it my way

Regrets, I’ve had a few

But then again, too few to mention

I did what I had to do

And saw it through without exemption

I planned each charted course

Each careful step along the byway

And more, much more than this

I did it my way

“Something Stupid” from The World We Knew (1967)

Sinatra’s version of this song was recorded with his daughter, Nancy. And while many have rightly raised an eyebrow at such an amorous track being recorded by father and daughter, if you remove that from the equation, the tune is one of the best love songs of all time. The lyrics put the idea of love on its ear; instead of taking the subject earnestly, the song looks at it with humor and a wink. On the song, Sinatra sings,

I know I stand in line

Until you think you have the time

To spend an evening with me

And if we go some place to dance

I know that there’s a chance

You won’t be leaving with me

Then afterwards we drop into a quiet little place

And have a drink or two

And then I go and spoil it all

By saying somethin’ stupid like, “I love you”

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