I was still a kid, working at the college radio station in Hempstead, New York. I was a little older than the other kids, because I was recently back from my short stint in the Marine Corps. I don’t remember who provided my entrée for that interview, but I remember the night. How could I forget?

As a kid, I listened to big band vocalist Sinatra on “78” records. He was special even then. By the early 60’s, Sinatra was an entertainment institution. Music, movies, television and the subject of myriad publications which alluded to political and criminal intrigue.

How many romantic evenings have all of us had — candles, cocktails and Sinatra playing? He was a legend, America’s most iconic celebrity.


Heady stuff for a young reporter invited to one of Sinatra’s hangouts. The story was about Jilly Rizzo. He ran a famous night spot in New York. “Jilly’s Saloon” (everybody just called it Jilly’s). It catered to lots of celebrities, but most notably Frank Sinatra and his “rat pack”. My primary focus that night was Jilly himself. We did a low-key chat about his club. Jilly did the talking. About his youth, how hard he worked to make his club a success. I let him talk, which he appreciated. He was fascinating. A real life Damon Runyon character.

The interview wrapped. I figured my night was over. Wrong. Jilly kept referring to me as “Kid”. As I prepared to leave with my engineer, Jilly tugged at my sleeve and motioned for me to follow him.

“Kid”, he said in his raspy voice, “I want you to meet some pals”. Jilly led me to a table filled with lots of cigarette smoke, profanity and laughter. I was a little nervous.

I had cause to be nervous. I made eye contact, my brain began to register and I began to smile blankly. Sinatra, Dino, Sammy, Joey Bishop and other familiar faces looked at me. My brain kept shifting gears. Apparently Jilly had introduced me as “Kid”, a newbie who was okay. That turned out to be my access card.

I realized I had a big glass of scotch in my hand. Frank Sinatra was talking to me, a big glass of scotch in his hand, a cigarette dangling from his mouth. I think I still had a glazed smile on my face.

“So, Kid”, he asked, “What the hell do you do that makes Jilly like you?”

I told him I had been listening to Jilly and found his back story fascinating. I told Sinatra I enjoyed listening rather than talking. It was easier, I volunteered. “You’re on radio and you like to listen rather than talk?”, he asked.

“Yes”, I said. I just stared at him.

He stared back, then said, “Kid, you’re okay”.


I slid into some questions about his childhood, about his weight, the difference between his singing and his conversational voice. Sinatra was off and running. The anecdotes had little to do with celebrity and lots to do with the guy behind the legend. I kept listening.

He noticed the tape recorder wasn’t running. Puzzled. I said this was social time. He looked even more puzzled, then shook his head and smiled. Sinatra said he wasn’t used to such treatment. I smiled. An easier smile.

I talked a little about my hearing problems, diction problems. My determination to get things right. Now Sinatra was listening. He said he too had diction problems during regular conversation which he tried to cover up with sarcasm and bluster. I realized he was leaning in as if to confide with me. I also noticed the other celebs had backed away, giving Sinatra privacy.

The conversation continued for another half hour, maybe 45 minutes. Jilly kept checking to make sure our drinks were fresh. I knew other people were staring at us. I figured they were wondering who the hell was this kid chatting up Sinatra. Actually, we were talking about music and radio. I told him about how I loved doing tight segues blending solo vocals, chorals, and instrumentals. He began giving me tips about how to segue some of his music. In a couple of cases, I was already doing it. He loved it.

We talked a little about sports. I told him I was a Brooklyn Dodgers fan and Duke Snider was my favorite player.

Sinatra said Joe DiMaggio and the Yanks were his favorites. I gave him a look and he smiled. Casey Stengel was our peace broker. Earlier that year, I’d spent time with Casey who was managing the fledgling New York Mets. Sinatra laughed at my recollection of conversation with Casey.

“Diction”, we both said and laughed.

Jilly Rizzo finally broke up the chat saying Sinatra was needed elsewhere. Sinatra grumbled, gave me a card and said there would be another time. There would be. Another story for another day.


Categories: Anecdote, Celebrities, Entertainment, Garry Armstrong, Humor, Show Business

Tags: , , , , , , , ,

43 replies

  1. I enjoyed living vicariously through your exciting nights with Frank Sinatra. The first one, here, really got your foot in the door. Being patient, listening and later, your second night knowing lines and impersonations, those really bonded you snd he. Thanks, Marilyn for sharing this space snd time with us, the readers with their slacked jaws hanging open. 😀


    • Oh, and of course the first comments were meant for Garry. Sometimes I write and don’t proofread.
      The thanks to Marilyn was meant to let her know that I realize how all of us may seem rapt in our attention to Garry, we very well know you are exciting to know, too.

      Liked by 1 person

      • I knew that 🙂 When Garry turns his computer on tomorrow morning, I bet he’ll know it too.


      • Thanks for the very kind comments. I’m double checking comments posted by folks who went to the link with my first Sinatra piece. Those Sinatra stories seem to have involved another me, long ago when our world was very young. I enjoy the memories.


  2. I don’t believe Frankie was all that easy to get inside of. So that’s quite a feather in your cap.
    Yet another.
    When I’ve met celebs I never think of anything smart to say?!
    Later I think of lots of stuff I could have said. ??

    Liked by 1 person

    • Marilyn and I were just discussing Sinatra, again, last night. I’d just watched his “The Detective” again for the first time in many years. Good film, great Sinatra. If you haven’t seen that film, you should check it out. Made in 1966, it’s a very true picture of the NYPD in those days .Anyway, back to Sinatra. He wasn’t the easiest or nicest guy around people. We just hit it off and I LISTENED. That seems to have been the key with those “legends” I’ve encountered.


  3. What a story, priceless bit of history, Garry. Thanks for sharing it with us.

    Liked by 1 person

  4. Dean Martin and I have an ongoing love affair, one he doesn’t know about. His music plays in my kitchen, when I cook an Italian feast…and everybody knows it. I think my husband and my friends would call the ambulance if I would cook an Italian meal without him. Frankie boy is in my workroom, when I have the need to sway 🙂

    Liked by 1 person

  5. You need to hurry up with the next story.

    Liked by 1 person

  6. Well…I think that qualifies as a MEMORY. 🙂

    Liked by 1 person

  7. Ah geez, this is in my top ten list of dreams – hanging with the “pack.” What an amazing story, what a gilded memory for you to treasure.
    Just for the record also on the list hanging with Hemingway, Mario Lanza and all early Impressionists in Paris:)

    Liked by 1 person

  8. Oh, to have had a video camera to film that chat….but Sinatra probably wouldn’t have been as relaxed. I absolutely loved his performances in “High Society” and “Guys and Dolls”.

    Liked by 1 person

    • I wish he’d at least have gotten a few stills, but he didn’t think about it, so he doesn’t have pictures. A few, but VERY few.


    • Most of my “hanging out times” happened because there were no cameras, microphones or tape recorders. I think that’s why those “legends” relaxed and shared personal time. In hindsight, I wish I did have photographic records but then I wouldn’t have these stories to share.


  9. Another great tale for the memoir, Garry. Nag, nag.

    Liked by 1 person

  10. Exiting experience Marilyn for you in such a young age 😀



  2. HAPPY BIRTHDAY OLE BLUE EYES – GARRY ARMSTRONG | Serendipity Seeking Intelligent Life on Earth

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