One for My Baby (and One More for My Dad)

The silky sounds of Sinatra and weighty wordlessness of male bonding echo among three generations of my Italian-American family.

Illustrations by Vinnie Neuberg

I. Flying to the Moon

Driving in the car with my father, he reaches over to turn on the radio, steering with his left hand. He puts on “The Imaginary Ballroom,” a program that plays Sinatra, Martin and Bennett.

Sinatra’s voice emerges warmly from the speakers.

“Yes, It’s alright with me,” Sinatra sings sweetly. The song is not full of bravado; it’s tender and hesitant. He’s telling a woman that she looks like his previous lover; she has sweet lips, too, like his old lover. He says that if she’s lonely one night, it’s alright if she kisses him with those lips. We never hear her response.

I hate to admit that it’s a great song and that Sinatra sings it dramatically and convincingly. I don’t want to like my father’s music — he desperately wants me to like it.

I look over at my dad; he makes the music louder.

There are parts of the song that Sinatra whispers. He’s pleading with the woman. This is not the Sinatra I had despised: a braggart, a gangster. This is the …