‘Michael Kay Show’ caller sings Frank Sinatra deep cut on air

Someone named “Richard from Manhattan” started out just like any other ordinary caller on The Michael Kay Show Thursday, talking about the New York Knicks.

But within 90 seconds he was schooling Kay and co-host Don La Greca on Frank Sinatra.

And then he began singing an old Sinatra song.

“You were talking about Sinatra songs. I am a Sinatra expert,” the caller said. “And his greatest song, and the song that should be sung after Yankees losses, is ‘Cycles.’ 1968 … he sings about how life, one day you’re up, the next day you’re down. I think it’s the greatest Sinatra song ever.”

“I have never heard that song, I’m going to have to listen,” Kay said.

“I’m sure I’ve heard it,” La Greca said.

“Fellows, I can give you a quick verse,” Richard said.

“Oh please, sing it,” Kay told him.

And so “Richard from Manhattan” sang some of Sinatra’s “Cycles.”

There isn’t much that I have learned

Through all my foolish years

Except that life keeps runnin’ in cycles

First there’s laughter, then those tears.

Kay’s first impression: “A little pitchy, dude. A little pitchy.”

La Greca got in a jab at co-host Peter Rosenberg, who was off Thursday.

“All I have to say is Peter, I hope you enjoyed your day off, because you missed that,” La Greca said. “We’re going to talk about being here live for that.”

“Forever,” Kay said. “For as long as this show goes on, ‘Where were you when?'”

La Greca asked producer Anthony Pucik if he’d known the caller planned to sing.

“Anthony, did you know that he was going to sing?” La Greca asked Pucik, joking the caller came “dangerously close to the whole ASCAP thing,” meaning the show would have owed royalties for using the song.

Then Pucik cued up Sinatra’s version of the song. Without warning, “Richard from Manhattan” started singing along, drawing hysterical laughter from Kay and La Greca.

“Sometimes, it’s so fun to do this show,” Kay concluded.

[The Michael Kay Show]