Melany Perez

If I traveled back in time to have dinner with one individual, I would sit in a cornered booth at Patsy’s on 56th Street in New York City. Across from me would sit a man with a cigarette perched between his lips, a tuxedo accented stylishly by a cautiously fixed bow tie and a fedora angled rebelliously on his brow over his iconic blue eyes. In short, I would share a meal with Frank Sinatra. 

Over the past few weeks, I found myself barraged by icebreaker questions as a first-year here at Yale. Beyond the requisite questions concerning my name, residential college, hometown and intended major came the wild card questions, and these wild cards seemed to escalate in creativity. One question came up over and over again: “If you could go back in time to meet anyone and have dinner with them, who would it be and why?” 

As someone who has responded to this query throughout my life, my answers have changed and ranged. My passion for political science has prompted me to answer with the likes of Abraham Lincoln, while my inner journalist has argued a compelling case for Edward Murrow. However, upon closer introspection, I decided to entertain the hypothetical with greater seriousness and, after much deliberation, found my resolute answer in Frank Sinatra. 

In terms of music taste, I have always been an outlier. Growing up as a young kid in the San Francisco Bay Area, all my friends listened to hip-hop and pop while I spent hours listening to my father’s Sinatra records. Even now, I find myself a preacher for the Great American Songbook among my friends who are lovers of country, listeners of pop and advocates of rock.  

My fascination for Sinatra’s craft and artistry is as nuanced as his life. And, like his life, it cannot be summarized in a humble reflection. My reasons for choosing to have dinner with Sinatra are far-ranging, but I choose to concentrate on one: his ability to deconstruct the complexities of emotion into relatable and timeless reflections on the nature of life through his repertoire of torch songs—ballads that concentrate on themes of lost and unrequited love. 

To those who know him little or even to those who know well as a vocalist, the first and most recognizable image is the Sinatra that swings — the crooner that effortlessly charmed his listeners with the playful sensuality he infused in Cole Porter’s “I’ve Got You Under My Skin,” the indefatigable bravura he exuded in “Fly Me to the Moon” and the unbridled charisma he carried in “I Get a Kick Out of You.” Other immediate associations direct our attention to the sentimentality he wove with “The Way You Look Tonight” or to “My Way,” an anthem of individual perseverance and grit, two qualities not altogether too distant from the story of his life. 

But the Sinatra that I came to appreciate as I got older was the lonely Sinatra, the one who enveloped himself in his torch songs. With every torch song that passed through his lips, Sinatra brought passion and sincerity in the way he carried a lyric, delivered a phrase and held a note. Whereas some singers concentrated on vocal perfection and musical accuracy, Sinatra was different because he focused on emotional accuracy. And this approach is best heard in his 1956 album In the Wee Small Hours

Countering the typified image of strong and masculine men of his era, Sinatra offered a realistic image — one with its share of natural weakness, vulnerability and loneliness at the heels of lost love. In his recording of Rodgers and Hart’s “It Never Entered My Mind,” he mournfully dwells on dashed dreams born of a broken heart. In Carmichael’s “I Get Along Without You Very Well,” he explores the difficulty in presenting a facade that conceals internal sorrow. In contrast to the confident and energetic Sinatra we are accustomed to, the playful Sinatra of the Rat Pack or the “Come Fly with Me” jet-setting bon vivant, his torch songs offer a deeper and more nuanced side to his artistry and his character. 

In the Wee Small Hours captures Sinatra’s unmatched and exceptional dedication to the songs he recorded. In his album A Man and His Music, he said, “I respect every record as if it’s the last song I’ll ever sing.” That meticulous mentality and sheer reverence for his work allowed him to infuse an element of himself to all his torch songs. With the lyrics and melodies of great songwriters and Nelson Riddle’s arrangements by his side, one can palpably feel Sinatra’s heart ache with every breath and his voice that was ever on the verge of cracking. He would hold a note dramatically as if he were freeing himself from a net of sorrow, or start a lyric a second late as if he were caught in the fleeting reverie of a love that was gone and past. His sobs did not take the form of tears rolling down his cheek but of the melancholy pining wrapped within every phrase he blanketed in blue. 

In his musical explorations of disconsolation, he gave consolation to the downhearted. In his songs of solitude, he offered his company to the downcast. In all, Sinatra delivered more than his stylish craft in In the Wee Small Hours. He shared his heart, the recesses of his innermost feelings and a palette of emotions that created, in the place of sorrow, artistic beauty. 

I have listened to In the Wee Small Hours many times in my life, and it took heartbreak of my own to realize the full scope of Sinatra’s talent, the breadth and depth of his repertoire and the incomparable ability he had in making that which is incomprehensible to some understandable to the empathetic many. For the first time in my life, not only were my feelings captured perfectly by the sentiments of popular lyrics but understood to the tee by someone so distant from me as Sinatra — but as close to me as any other individual who has ever loved would be.  

In many respects, to label Sinatra merely as a singer is—if not a gross understatement—a misnomer. He was more than a singer — he was a translator of the emotional spectrum, a storyteller of the human condition and a companion his listeners could lean on.

It is hard to find a contender for an artist who can speak to the human heart and all its complexity than Frank Sinatra. His songs are for those with hearts beating and hearts aching, for those who have fallen in love or fallen out of love and for those hopeful and hopeless romantics. With this emotional range in his artistry, his relevance has transcended generations due to the universal applicability of his songs to many aspects of human life. In short, Sinatra accomplished what only a small cadre of artists have done in the history of music — immortality.

So, if I were to travel back in time and have dinner with one individual, I, without hesitation, would share a meal with Ol’ Blue Eyes. I would not ask for a song or performance. I would not ask him to dissect his technique or style. I would not ask for a photograph or autograph. All I would do is offer my thanks and gratitude to someone who was, and indeed remains, extraordinary.