TOP 5 SINATRA TRACKS OF ALL TIME (RANKED)
Dear Readers/Subscribers,
Well, it looks like my Sinatra obsession isn’t waning one bit, and though I’m less of a zealot about converting those immune to his musical charms, I still like to do my bit for the cause when I can.
Those who know me well will understand just what an impossible task I’ve set myself here: selecting a mere five Sinatra tracks and whittling them down into a concise list of his best recorded songs ever. It would be easy enough to knock up a quick top 25, 50, or even 100, but I decided I didn’t want to bore anyone (including myself). Besides, the stringent challenge of choosing a zen five feels like a far more interesting proposition to my mind.
So, with no further ado, here are my top five Frank Sinatra tracks (ranked).
And for the easiest way to access the video links while reading (if I can be so presumptuous as to believe you might), you may prefer to view in browser (see above, just below the blog title heading).
Yours, come rain or come shine,
Digital Renegade
5. Come Rain or Come Shine (1962) - Reprise Records
This track is remarkable for the way it builds to a near-operatic climax, as Don Costa’s epic orchestration matches the full range of Sinatra’s vocal and emotional expression—from understated, mono-legato dismay to snarling, cymbal-clashing defiance. Though there have been a few great versions (including Ray Charles, who is synonymous with it), Sinatra elevates the song to new heights, ascending its mountainous peaks while honouring the depths of its Depression-era sentiment.
4. She’s Funny That Way (1960) - Capitol Records
The first time I realised this was a special song was when Radio 2’s Benny Green spoke in awe-filled reverence about the perfect two-octave descent Sinatra delivers toward the end of this version of She’s Funny That Way, originally made famous by Billie Holiday. Sinatra was a huge fan of Holiday and even paid for some of her rent and medical bills when she was strung out on heroin.
What is so sublime about Frank’s rendition here is the weary, resigned tone that captures the entire sentiment of the song—somewhere between resignation and appreciation of a love that won’t let go, despite the protagonist’s self-confessed flaws.
3. I Thought About You (1956) - Capitol Records
There are so many classic swinging tracks in Frank’s discography that it seems almost blasphemous to choose just one, but there’s something so cool about the way this infectious swinger creeps up on you—like a memory from the past catching you when you’re least expecting it, which is exactly what the lyrics are all about.
I took a trip on a train
And I thought about you
I passed a shadowy lane
And I thought about you
Coming from one of the most famous albums of his Capitol 1950s era, Songs for Swingin’ Lovers!, the fact that this track sticks in my mind even more than I’ve Got You Under My Skin or You Make Me Feel So Young should give you some indication of its enduring greatness in my estimation.
I don’t take this stuff lightly.
2. In the Wee Small Hours (1955) - Capitol Records
Given that it’s the 70th anniversary of what I believe is the greatest album of all time, it was inevitable that the gorgeous, nocturnal title track would feature high on this top-five list—so here it is, at number two in the ranking of the best Sinatra songs of all time.
Though there are so many masterpiece tracks on this entire album of post-midnight heartbreak, this is the one that sets the tone for the whole project. It puts you in that Edward Hopper place: a lonely street scene where it’s just you, your broken heart, and a lamppost.
Sweet sorrow has never been more heartfelt, magical and cinematic.
1. Young at Heart (1954) - Capitol Records
King of the hill in this top five is Young at Heart, probably the first Sinatra track that ever caught my attention, while I was watching the final scene of Woody Allen’s McCarthy-era comedy The Front.
Since that fateful moment, the song has become a kind of credo for life, promoting the optimistic idea of staying young at heart so that you can fend off the inevitable demons of aging—those that can eat away at your self-worth and taint your worldview.
Here, the answer is simple: find joy where you can to preserve the youth in your spirit and in your heart. That way you’ll at least be a little happier, if not entirely free of the inherent suffering of existence that we all must endure.
Sinatra’s ability to sing carefree vocals for a song like this on the one hand, and a torch song of suicidal despair on the other, points to his incredible emotional range—the American Songbook equivalent of a great Shakespearean actor.