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, not just for him but for 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 five songs, and it's about life and remembering the ones you loved the most.

2 New York, New York

One of the best. This song is a classic.

I want to 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.

Number one in my opinion. And I'm not even a New Yorker. Followed by Feeling Good.

3 Fly Me to the Moon

This belongs at #2. The argument can most definitely be made for #1, though. A very amazing song. Always impresses me when I hear 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 that if you sing this to a chick, she'll instantly love you should put this at number one.

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

5 Strangers in the Night
6 Come Fly with Me
7 That's Life
8 You Make Me Feel So Young

This is one of Sinatra's 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 concert. I 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.

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
12 Let It Snow! Let It Snow! Let It Snow!
13 Something Stupid
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 reveals your emotions through his own. Listen to the lines - you were there. This is a gift to us all. Another timeless moment captured, from youth to maturity. Worth a million listens, and then some.

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. It's the opening salvo on one of the greatest albums ever made (eponymously titled).

18 Luck Be a Lady

James Bond here? No, better. Bigger. Cooler. We're in Frank's 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 think he would know!

19 Night and Day
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 in the top ten.

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