Frank Sinatra is Not Amused: Letters from the King of Swing


20th Feb, 2013

Our first letter comes from Frank in 1976, addresed to the Chicago Daily News writer, Mike Royko, who had just published an article questioning the special treatment Frank had received from the Chicago police while in town for a concert. Here is how Sinatra felt about the piece and its writer…

1. “Quite frankly, I don’t understand why people don’t spit in your eye three or four times a day”.

via Stupefaction

The article was printed in the Chicago Daily News Writer the next day by Royko, along with an apology from the columnist, admitting it was a thrill to get a letter from Sinatra, as he was actually a fan of the singer, “even if he did call me a pimp.” Royko concluded that Sinatra’s extra police protection must have come from a politician trying to impress the singer and added, “If you say you have no flunkies, I take your word and apologize. I’ll even apologize to the flunky who delivered the letter.”

The letter was auctioned off the same year and won by a lady from Wisconsin for $400. It stayed hanging on her wall for more than 30 years until she discovered at an antiques roadshow that it was worth upwards of $15,000.

2. “Come on George. Loosen up. Swing, man.”

Our next letter was written as an open letter to George Michael in 1990 after the former WHAM singer announced his plans to get out of the lime light in an interview with the LA Times, stating he would not be doing any interviews, music videos or going on tour for his third album. Fans were not happy and Frank Sinatra was not amused…

3. Nobody puts Sinatra in the Corner

In what seems a rather protective fatherly note to his daughter Nancy, here is one Frank wrote in the late 1960s.

And unless you have superhuman eyesight, the typed transcript is below…

Chicken — a thought.

Strange, but I feel the world we live in demands that we be turned out in a pattern which resembles, in fact, is a facsimile of itself. And those of us who roll with the punches, who grin, who dare to wear foolish clown faces, who defy the system — well, we do it, and bully for us!

Of course, there are those who do not. And the reason I think is that, (and I say this with some sadness) those up-tight, locked in people who resent and despise us, who fear us, and are bewildered by us, will one day come to realize that we possess rare and magical secrets, and more — love.

Therefore, I am beginning to think that a few, (I hope many) are wondering if maybe there might be value to a firefly, or an instant-long roman candle.

Keep the faith



Hope you enjoyed today’s snooping session!

PS. Here’s an old photo of Sinatra’s doorbell.

Sources: Letters of Note, Stupefaction,




You might also like


More in Conversation StartersEditor's PicksInspiration VaultLife is MessyMovie / Music / Book Junkie

Hot Off the Press

Editor's Picks

Processed with VSCOcam with s3 preset

Your Office on Cloud 9 in Paris

I remember moving to Paris and not really knowing where to start. In fact, I probably took a lot longer than I should have to rev my engines because I just didn't have a place to go and plan worl...

Trending 2,682

The Messy Nessy Chic Holiday Book List

Don’t count on me as a book critic here and I’m certainly no literary connoisseur, but one thing you might be able to rely on is that I’m not bad at sniffing out a good story. And by now, I th...

Trending 3,332

The Fashion World’s Best Kept Secret

If you asked me to name three fashion photographers off the top of my head, I would probably say, Mario Testino (easy one), Annie Leibovitz ... and does that guy who photographs everyone on the st...

Trending 3,542