Top 10 Best Frank Sinatra Songs

With a career spanning more than half a century, Frank Sinatra bestowed upon the world a treasure trove of melodious gems that continue to resonate with audiences of all ages.

What makes Sinatra's catalog so special is its rich variety. From heartfelt ballads to swinging jazz numbers, Sinatra's unique voice and unrivaled phrasing breathed life into every lyric he crooned. Whether he was singing about the highs and lows of love or providing his own twist on the American Dream, Sinatra's songs have the uncanny ability to transport listeners, making them feel as if they're part of the story he's weaving.

The best Sinatra songs? That's subjective, of course, since his music appeals to different people for different reasons. Some may lean towards his softer, more romantic ballads while others may be more drawn to his lively, foot-tapping tunes. No matter your preference, the one common thread that runs through all Sinatra's best work is his uncanny ability to connect with the listener, sharing a piece of himself in every track.
The Top Ten
1 My Way

I really like this because it's him celebrating life for not just him but everyone else listening. I feel that it's a song full of emotion and I really really like it.

One of my favorite songs by Sinatra. And unlike some people my age, it has nothing to do with the fact that Jon Bon Jovi name drops it in "It's My Life"

I love this song it's one of my top 5 songs and it's about life and to remember the ones you loved the most.

2 New York, New York

It's kind of ironic that both New York City and Chicago both are an inch away from being called wastelands. Still, good song.

One of the best, this song is a classic.

I wanna wake up in a city that never sleeps and have this song playing in the background. One of Sinatra's best, besides Under My Skin and My Funny Valentine.

3 Fly Me to the Moon

This belongs #2. The argument can most definitely be made for #1 though. An very amazing song. Always impresses me when I heard it!

Best Frank Sinatra song, and one of the greatest songs of all time.

It's so relaxing and calm yet wonderful.

4 The Way You Look Tonight

Just the fact if you sing this to a chick and she'll instantly love you should put this at number 1.

The song that got me into Frank Sinatra. Definitely the best of his songs

5 Strangers in the Night

Its best song ever

I love this song!

6 Come Fly with Me
7 That's Life

The best Sinatra song

The best of the best

8 You Make Me Feel So Young

This is one of Sinatras songs that I sing And imitate perfectly. He was the best of all time in my opinion. I was lucky to see him twice in concerti like and can sing all of these

My personal favorite Sinatra song (along with Fly Me to the Moon), I'm surprised it only made #35.

I'm the guy who said the last comment, and I'm very glad it's gone up to 17.

9 Summer Wind

His songs are timeless, like artfully carved masterpieces, each and every one. Summer Wind is a movie of sound...

I love this song so much. It's absolutely perfect for this time of year.

Just love the melody and words. One of my all time favorites.

10 I've Got You Under My Skin
The Contenders
11 My Funny Valentine

Best song ever!

12 Let It Snow! Let It Snow! Let It Snow!
13 Something Stupid

Great duet with his daughter.

My personal favorite

14 The Best Is Yet to Come

Get this song higher up on the list.

15 It Was a Very Good Year

What a beautifully realized song. Francis revealing your emotions through his own. Listen to the lines, you were there. This is a gift to us all. Another timeless moment captured, from youngster to maturity. Worth a million listens... And then some.

Unforgettable in fact.

16 All of Me
17 In the Wee Small Hours of the Morning

A truly beautiful song--a rendition that is unsurpassed, full of an achingly gorgeous melancholy--the opening salvo on one of the greatest albums ever made (eponymously titled).

His voice at it's peak!

18 Luck Be a Lady

James Bond here? No, better. Bigger. Cooler. We're in Franks world now, baby! Tux and Tie, so listen up! Tunes like this only come along once in a thousand years! Best of Francis Albert!

His road Manager Dick Curtis said Mr Sinatra's personal top favorite to sing live. I would this he would know!

19 Night and Day

I Get a Kick Out of You should be in the top ten, as well as Come Dance With Me. Night and Day should be higher.

20 I Get a Kick Out of You
21 Somewhere Beyond the Sea
22 The Lady Is a Tramp

A beautiful song about the meaning of true class. Genius.

It just got better over the years - amazing!

Not the very best, but at least the top ten.

23 Softly, As I Leave You
24 I'll Never Smile Again
25 Let Me Try Again

Story of my life in four words.

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