To say Frank Sinatra is one of the most famous singers in the world is an understatement. He has been immortalized, known by all folks ranging from eight to ninety-eight and for good reason. With a career spanning over sixty years, his talent and original sound has made Time Magazine’s collection of “The 20th Century’s Most Influential People” include him, even when faced with controversies.
Frank Sinatra’s career skyrocketed in the 1940s and the effect he had was comparable to “Beatlemania” of the sixties, but instead of girls in miniskirts and turtlenecks screaming and fainting…his fanbase was bobby soxers. Sinatra had a tougher time winning the approval of men of the early forties as their resentment for him grew. From not serving in World War Two due to his inadequate weight or swooning their women to a point of violence, he had many obstacles to overcome as for PR.
But the point of this article is not to give you insight into Sinatra’s personal life, we are focused on the art! The music! The indisputable talent of Frank Sinatra and his best songs! No, I will not be listing his greatest hits such as “Fly Me to the Moon” or “My Way” (although they are classics). I am homing in and focusing on songs from his early career that struck a chord with Americans of that time and led him to become one of the greats. These songs are intimate in feel yet euphoric. Sinatra’s tone brings out the intricate subtext of these heart wrenching lyrics and the composition of the music tops the many versions performed by others- no one does these songs justice like Frank Sinatra.
Get ready to expand your taste in music and expose yourself to Sinatra’s genuinely best songs.
5. “All or Nothing at All”
Starting off in Harry James Orchestra fashion, the trumpets cascade as a grand announcement to the listener, rather than just an intro, that a musical experience is about to begin. Twenty-five-year-old Sinatra uncovers the distressing lyrics written by Jack Lawrence as he sternly sings his way through, yearning for a love as equally unwavering as his. This no-nonsense theme of wanting someone to fully commit or leave you alone is contrasted by the softness of the romantic music backing Sinatra’s vocals. Composed in 1939 by Arthur Altman, the arrangement combined with Frank Sinatra’s indisputable voice, paints a beautiful picture of a self-assured man who struggles to want a deep connection yet knows solitude is a more favorable outcome for him.
In the age of social media and hook-up culture, this single is more relevant than ever. “All Or Nothing At All” is about not playing games and wanting your interest to communicate clearly their desires. This is the purest form of unapologetic! The way Sinatra firmly draws his boundaries right at the beginning in a confident manner then slowly shifts to desperately pleading with his lover not to cross them because he knows he would fold, tragically shows the beauty of someone who knows that they could not handle a casual affair. This version reissued by Columbia Records in 1943, sold over a million copies. Eighty years later, this song is still guaranteed to strike a chord with all you “old fashioned” souls out there.
Best line: “If it’s love, there is no in between.”
4. “You’ll Never Know” (With the Bobby Tucker Singers) 78-rpm
If there is one song that screams 1940s, this is it. Based off a poem written by Oklahoma war bride Dorothy Fern Norris, Sinatra’s version (recorded in 1943) brings tears to my eyes every time I hear it. Originally transcribed into a song by Harry Warren and Mack Gordon for musical “Hello, Frisco, Hello,” this song won an Academy Award for Best Original Song. Frank Sinatra’s version spent two weeks at number two on Billboard’s Charts.
Accompanied by the Bobby Tucker Singers, the arrangement by Alec Wilder bellows gently and exudes the feeling of weeping. Bone deep sorrow comes across in Sinatra’s voice as he professes his love. Lyrics like “I speak your name in my every prayer,” and “If I tried, I still couldn’t hide my love for you,” would typically be taken in a romantic way, but there is a sense of discouragement to this song. He continues to state that it is hopeless if that person can’t understand how strong his love is and he swears that he has tried everything to show his love. The listener is stuck with a pit in their stomach and a lump in their throat due to this sobbing tune of unreciprocated love.
Best line: “You went away and my heart went with you.”
3. “Polka Dots and Moonbeams”
In most of Frank Sinatra’s songs, singing purely about his feeling towards someone takes precedent over a storyline. In his first hit with Tommy Dorsey, Sinatra holds our hands as he guides us through the narrative tale of love at first sight. This 1940 song composed by Jimmy Van Huesen and written by Johnny Burke takes a creative approach to a meet cute. Instead of pointing out the beauty of the person Sinatra bumps into at this country dance, he states that all he saw was “polka dots and moonbeams,” reflecting the unexpected frenzy and bewilderment you feel when a per chance encounter hits you.
Sinatra perfectly expresses the nervousness of dancing with a stranger you don’t want to lose. As the song progresses, he leaves us sitting on the edge of our seat as he continues to push the envelope of the relationship. From holding his breath to ask for another dance to ending the song, living with this person, seeing “polka dots and moonbeams” for the rest of his life, this is a great happily ever after story that expresses how frightening love can be when you put yourself out there. With a perfect tempo, this song makes you want to put on a polka dot dress and go swing dancing- even if it’s just in your kitchen.
Best line: “There were questions, but my heart knew all the answers and perhaps a few things more.”
2. “These Foolish Things (Remind me of you)”
Time to get nostalgic- I must boldly say this is Frank Sinatra’s most bittersweet song. He swoons us with enchanting lines like “the winds of March that make my heart a dancer” or “a fairground’s painted swings,” then smacks us with the harsh reality of “these foolish things remind me of you.” Throughout the song, Sinatra continues to state romantic scenarios only to verify that they are just memories now. In this ballad with music by Jack Strachey and lyrics by Eric Maschwitz aka Holt Marvell, Sinatra’s version best showcases the haunting effect of every experience reminding him of the person he still loves.
Maschvitz’s strategic choice of describing these experiences as “foolish” captures the need to patronize the heartbreak we feel. In this arrangement by composer Axel Stordahl, the deep-rooted hurt is projected through the strings, rather than the upbeat, earlier version performed by Carroll Gibbons (which I still love.) Frank recorded this beauty in 1945 with Columbia Records and still has us thinking about the lasting effects and torment of a carefree, youthful love.
Best line: “A cigarette that bears a lipstick traces. An airline ticket to romantic places.”
1. “I Fall in Love Too Easily”
Let’s end this by clarifying…the Chet Baker version is a cover. Yes, this song was originally sung by Frank Sinatra himself in the 1945 film “Anchors Aweigh” starring him and Gene Kelly. This song is undoubtedly iconic for many reasons. This tune was ironically known by his wife as Sinatra’s theme song to his personal life. With many versions following, nothing beats the cinematic experience of Sinatra’s performance. Being a Southern California native, there is something amazing about watching Frank Sinatra play piano at the Hollywood Bowl in 1945 and express his troublesome heart as a “sailor” that finds himself flustered. His execution of this song is too believable and that is what makes it top the rest.
Composed by Jule Styne and lyrics by Sammy Cahn, “I Fall in Love Too Easily” was nominated for Best Original Song. The grand arrangement builds exquisitely as the lyrics remain simple, giving each line more weight than the former. Many of us have been in that position of self-realization and know the feeling of taking responsibility for a romance falling short. Human nature is highlighted and patronized at the same time in this ballad. Sinatra expresses how no matter how much wisdom he obtains, he will still fall hard and hap hazardously- plain and simple. This song sums up the basic understanding of that at the end of the day, we will follow our hearts over logic every time.
Best line: “My heart should be well-schooled ‘cus I’ve been fooled in the past.”
Happy listening! Be careful though, these songs may lead to the side effect of hopeless romanticism.
If you liked this song lists, reach out to me!
What a great article.