12 Most Sensational Songs by Frank Sinatra

12 Most Sensational Songs by Frank Sinatra

I  fell in love with Sinatra at the age of 20, and it’s been a life-long romance for me. He’s kept me company during the tough moments and helped me celebrate the wonderful ones. His catalog of music is staggering, his range is remarkable, and there’s no one, but no one who can turn a phrase of music into a magical moment the way he could. He was a storyteller, and seducer, and a legendary performer.

To add a little romance and spice to your Valentine’s Day, let me share with you 12 of his most memorable, and timeless tunes. Mr. Sinatra’s closing line at his shows was often, “May you live to be a hundred, and may the last voice you hear be mine.” It doesn’t get more romantic than that!

1. The Way You Look Tonight

I may be a bit biased, as this was the first dance at my wedding 22 years ago, but the slow start, the perfect diction, the build up in the middle with the horns coming up underneath the strings… and then the quiet ending — well, it’s pretty fabulous.

2. Young at Heart

A bit on the sweet side, but lovely nonetheless. This was Sinatra’s comeback song after being off the charts for many years, and it defines his attitude and his view on life — never stop having fun, never stop enjoying it all.

3. I’ve Got You Under My Skin

Classic Sinatra, with everything you could want from him. Romance, desire, passion, with that old-fashioned feel that makes me weak in the knees. I dare you to not fall in love with this voice after listening to this one.

4. One for My Baby (and one more for the road)

Sinatra had a bit of a rough patch during the late forties. His career was on the downswing, his marriage to Ava Gardner was ending, and there was a time when he was thought to be finished. He proved all of the doubters to be wrong, as some of his best songs were recorded after these difficult times. This song brings all of his pain, his angst, and suffering to a beautiful musical conclusion. You can just see him sitting in a saloon somewhere, crooning to the bartender.

5. I get a Kick Out of You

Was there ever a more perfect pairing than Sinatra and Cole Porter? The pure joy of Porter’s lyrics, as interpreted by the shoo-be-do-be-do of Sinatra — it’s a fizzy concoction of loveliness.

6. Send in the Clowns

There have been dozens of recordings of this song, one more beautiful than the next. But when Sinatra sings it you can really feel his wistful, nostalgic state of mind. This video was recorded in the mid-sixties, when he was turning the corner to the young side of old, but wow was he handsome.

7. Love Me Tender/Witchcraft with Elvis Presley

I had to sneak this in, even though it’s not pure Sinatra. The combination of these two legends, singing two great songs, and having such a blast doing it is so charming, and a visual affirmation of the charisma Sinatra and Elvis both oozed in their prime.

8. Fly Me to the Moon

The orchestra really makes this song soar. Its a classic, and yet another example of the skill Sinatra had with phrasing. You can just imagine sitting in a nightclub, sipping a martini and smoking a Pall Mall, watching beautiful couples all dressed up and dancing. Mad Men, anyone?

9. Night and Day

Oh the drama, the passion, the ooh la la you can feel… this song is one of the most romantic Sinatra ever recorded. Play this and swoon.

10. Come Fly with Me

Jimmy van Heusen and Sammy Cahn were a wonderful song-writing team, and Sinatra sang many of their songs over the years but this one is the best. Up, up, up we go with him, as he urges us to take off to Peru. Who wouldn’t?

11. The Lady is a Tramp

What does this song really mean, anyway? It doesn’t matter. If you listen to the words, it makes no sense — but it’s so much fun, who cares?

12. My Way / New York, New York

In my younger days, when the bars closed at 2 am, one of these songs was always played. I can’t remember the last time I was in a bar that late, but these two songs always signaled the end of a good night to me. If I never heard “New York, New York” again, it would be ok with me — but hey, it’s a love song to my hometown — and hey, it’s Sinatra!

Share your favorite Sinatra tune if it’s not on this list. Because there are so many more fabulous songs to listen to from Old Blue Eyes, the Chairman of the Board — Frank Sinatra.

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Featured image courtesy of Epiclectic via Creative Commons. 

Sharon Greenthal


Sharon Greenthal is a former stay-at-home mom, now empty-nester. She lives in Orange County, CA with her husband Peter and their perfect dog, Lambeau. Her two children are away at college. Sharon blogs about her observations the world around her, from the important to the inconsequential.

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@NurseLovesWine so great, my dad will love this!


#1 - #3 are a few of my all-time favorites, Sharon. I especially love it that my 18-yr and 17-yr old daughters love Sinatra/Rat Pack - passing the love of good music to the next generation!

Peg Fitzpatrick
Peg Fitzpatrick

Great list @sharongreenthal — I loved Frank in Guys & Dolls. My mom used to listen to that record over & over again. She loves him!


@V_N_O J'adore Sinatra, surtout les périodes Capitol et Reprise


@jodiokun I saw Frank in Tahoe years ago! He will always be the Chairman of the Board!


Nice list, Sharon. Frank was THE MAN.

If this list went to 15, I'd have to add: 'I Won't Dance', 'For Once In My Life' and 'Summer Wind'


@dbvickery one of my favorite memories of my daughter was when she was 4 years old, singing along to "The Lady is a Tramp" at full volume. Funniest thing ever!


@deleted_2698155_BruceSallan1 I too love Dean Martin and Sammy Davis Jr. They were both such talented and charismatic singers.

I saw Sinatra twice, but by the time I did he was way past his prime and was a little too old to still be doing his swingin' thing.


@Peg Fitzpatrick Guys and Dolls is my all-time favorite musical. Sinatra was by far the best thing about the film - Brando was horribly miscast - but I know that soundtrack by heart from beginning to end . Your mom has good taste!