Sinatra Was Cool

My father was strong and healthy most of his life. Though a heavy smoker for nearly sixty years, it wasn’t until he turned eighty that he began to fail. But once that decline began, it was mighty. When he died at eighty-five, Dad had spent five years of medical hell, trying to fight a myriad of ailments:  stroke, collapse of his kidneys, throat cancer, congestive heart failure. He never gave up until the very end, when he refused the dialysis treatments that were keeping him alive.

During Dad’s final years I did my share of taking him to doctor appointments and seeing to his medical needs. Though it was hard to watch a parent slowly pass away, I found that our time together helped us grow closer. For most of my life, Dad and I had a cordial relationship at best, never discussing personal matters that impacted our lives.  Conversation was limited to topics such as the rising cost of gasoline or the decline of our hometown. When I told Dad, some twenty-five years before he became ill, that I was gay, he couldn’t accept it and neither of us ever mentioned it again. Still, I loved my father—but from a distance.

There was one thing he and I agreed on, though: a love of music. Unlike me, Dad never owned a high-quality stereo or collected every album by a favorite singer, but when I stopped in to visit I’d often find him listening to music while playing solitaire on the computer. Before heading off to a doctor, Dad would already have the car radio tuned to his favorite station.  It was always big band music, with their star vocalists: Tony Bennett, Al Martino, Steve Lawrence—and Frank Sinatra.

As Dad’s passing drew near, he was transferred to his hospital’s palliative care room, which provided many comforts of home, including a CD player. Maybe your father has some music he’d like to hear, his nurse suggested. We brought in a few CDs, and as Dad slipped into a coma, and as one empty day became the next, Frank Sinatra provided some respite.

In those years of Dad’s decline I wrote a lot about him and our relationship.  They were quick poems, dashed off in between hospital visits and ambulance rides, and they became a kind of stress relief as I watched my father die. One of those poems was about listening to Sinatra in that palliative care room and how so many of his songs seemed to define Dad: “My Way,” “It Was a Very Good Year,” “That’s Life,” “New York, New York.” It was as if Frank was singing my father’s life story.

There hadn’t been time to reflect on those poems while Dad was so sick, but about five years after he passed I was ready to give them a closer look. I began spending time with each poem, searching for the right words to define our complicated father-son relationship. I brought them to writing classes, where, as it’s said in literary circles, I “workshopped” them. But actually, I was workshopping myself. Spending time with those written memories of my deceased father helped me come to terms with our lifetime of differences.  

Whenever I’m immersed in a writing project, I surround myself with resources to support my work. To help me think about Dad I bought some Frank Sinatra music, splurging on a 100-song set of his classic tunes. For months I had those songs on continuous play, becoming intimately familiar with them. I started by analyzing the songs’ lyrics, thinking they would reveal truths about my father. But it was something beneath the words that helped me better understand Dad and, as I was to discover, me.

It was how Sinatra sang those songs. He made each one his own, often recording the definitive version of timeless tunes from the Great American Songbook. After repeated listenings, I began to see (or, better yet, hear) what made Frank’s singing so special: The guy was smooth. He was classy. And he was in control. Take a listen. (I’ve suggested several songs that illustrate Sinatra’s suave style, but if you’re in a hurry, just one will do.)


Click here for “Nice N’ Easy”  

Click here for “They Can’t Take That Away From Me”

“I’ve Got You Under My Skin”

For a lot of years, Frank ruled the world of popular music. Before Elvis, or John and Paul, women wanted him and guys dreamed about being him. One of those guys was my father.  As I worked on Dad’s poems, looking for clues of what made him tick, I was bewildered by the difference between Frank’s swagger and my father’s more reserved, almost reclusive, nature. Why was Sinatra so important to Dad? My big breakthrough in understanding the link between the two men came when I began to notice a shift in my self-perception. After several months of listening to Sinatra singing, I’d started to think of myself as a confident writer.  When with a group of people, my normally quiet nature became more animated. I felt in control of my life. Frank’s cool demeanor, it seemed, had rubbed off on me.

If Sinatra’s singing style could have boosted my confidence in just a few months, what might he have done for my father, who admired him for decades? Did listening to his musical hero help Dad feel more self-assured? Had Sinatra helped ease my father’s pain as he privately shouldered life’s challenges?

I’ll never know for sure if Sinatra altered my father’s self-perception, just like he and I will never get to try to resolve our many differences. But I did figure out one more way that my father and I were in agreement: Of all the singers in the world, Frank Sinatra was the coolest. Though we came to that conclusion separately, whenever Sinatra sings, it feels like Dad and I are enjoying him together. Thanks, Frank.


Is there a song or singer that reminds you of your father or mother?