The Time I Made Sinatra Smile

The mission was so impossible, not even Tom Cruise would have accepted it.

“I just got off the phone with the client at Hiram Walker. I told him we’d try and get Frank Sinatra to endorse Canadian Club.” That was how James Michelson, president of SMZ Advertising, announced the 1985 Christmas ad campaign to the account group.

“But Jim,” someone chuckled, “the whole world knows that Sinatra’s choice of whiskey is Jack Daniel’s. He’s probably never even tasted CC.”

Sinatra Daniels 2

“Well, I said we’d do our best,” Jim said. Then he looked at me—his senior writer/producer for more than seven years—and I began pinching my leg under the table.

“Jon, we’re leaving for Atlantic City on Wednesday.”

In fact, there were three reasons why we thought we could get close enough to the Chairman of the Board to pitch this outrageous idea.

First, the agency had a long history of creating ads for Hiram Walker brands, many of which (like these) featured celebrities.

As for me, I’d already written and produced four award-winning videos for HWI’s pre-holiday sales meetings. The most recent featured the extraordinary talents of singer/impressionist Fred Travalena, whose take on Sinatra was considered the best in the business. One of the meetings was scheduled for Atlantic City on October 10.

Fred Travalena in full makeup.

Second, Jim Michelson was an old college buddy of Steve Wynn, owner of The Golden Nugget in Atlantic City and maybe half of the Las Vegas strip.

And third, Sinatra was set to perform at The Golden Nugget October 9-13, generating tremendous excitement for his first New Jersey appearance in over a year.

The stars certainly seemed to be in alignment. But would the biggest star of them all shine for us?

On the plane to Atlantic City, I thought about my four previous projects, so highly successful and entertaining. 

Gunther PDVD_108
Famed animal trainer Gunther Gebel-Williams customized his signature pose for us. The leopard behaved well: he only ate two cameramen.

In 1982, we’d linked up with The Ringling Brothers and Barnum & Bailey Circus. We won a medal at the International Film and Television Festival of New York, and my career writing commercials had added an exciting new dimension: long-form video.

Joe Namath wasn’t comfortable singing and dancing, but he found four reasons to rehearse.

The following year, we reached those hard-boiled liquor salesmen with a hard-boiled athlete—football’s greatest character, Broadway Joe Namath. Joe was an enthusiastic spokesman. And in screenings around the country, the film got standing ovations.

Fred as Reagan with Jon and Willie
Fred Travalena’s dead-on impressions included Ronald Reagan (posing with me on the right) and Willie Nelson.

We then hit back-to-back home runs with our 1984 and 1985 Hiram Walker holiday presentations. Fred Travalena, starring in both videos, was incredible as Richard Nixon, Ronald Reagan, Rocky, Clint Eastwood, Johnny Mathis, Johnny Cash, Sammy Davis Jr., Willie Nelson and many more.

Julie Miller
Julie Miller as Marilyn Monroe and Carol Channing.

For the 1985 video, Fred was joined by the terrific Julie Miller impersonating Marilyn Monroe, Carol Channing, Cyndi Lauper and Dolly Parton. Julie had recently been named Atlantic City’s Entertainer of the Year. [Author’s Note: See a video of Julie in the KatzTale “The Time I Slept with Miss December.”]

But it was Fred Travalena as Ol’ Blue Eyes that provided both videos with a fabulous finish. Here’s a brief sample:

We screened “We’ve Got Excitement”—the theme of the 1985 Holiday Presentation—for New Jersey distributors on October 10. It was a phenomenal hit, with several minutes of applause and whistles. Jim Michelson and I stood in the back beaming, along with Jim’s teenage son Jamie (who would later become the third generation of SMZ Advertising principals).

The next morning, we played the Sinatra segment for Steve Wynn. He was impressed. But when asked about Sinatra’s endorsing Canadian Club, Wynn was quite “frank.”

“Not a chance, fellas. But look, he’s got two shows tonight. You guys pick the one you want, and I’ll take care of you. In between, you’ll join us for dinner. You can talk to Frank yourself.”

I put in for the early show; Jim and Jamie preferred the after-dinner performance. And so, in a few hours, I would do what my mother had done forty years before at the Paramount Theatre in New York—see Frank Sinatra live onstage.

This was a much-anticipated homecoming for the Hoboken-born crooner. And one that many thought might never happen—mainly because Sinatra had said so.

Almost two years earlier—December, 1983—he was appearing at the same Atlantic City hotel. Later one night he was at the blackjack table with wife Barbara and pal Dean Martin. At one point, Sinatra confronted the dealer—a Korean-born female—and demanded that she give them cards from a single hand-held deck, instead of the standard six-deck “shoe.” In this way, it would be much easier for them to keep track of the cards already dealt.

When the dealer explained that his request was illegal in New Jersey (though legal in Nevada), Sinatra allegedly shouted, “You don’t want to play one deck, go back to China.”

Regarding the blackjack incident in his hotel, Steve Wynn (c.) said his pals Dean and Frank “were just out to have a little fun.”

The New Jersey Gaming commissioner publicly called Sinatra an “obnoxious bully.” Sinatra announced in response that he would no longer perform in the state … ever.

Some months later, a state assemblyman pleaded for him to “return to New Jersey, the home of your parents Dolly and Marty. Come back to your roots, Frank. Come home.”

It touched a nerve, and Sinatra agreed. He said, “It is time to place an unfortunate incident behind us … and time for me to return and perform in New Jersey.”

And when he did, I was there.

Presenting myself at the showroom, I was led to one of the long tables that run perpendicular out from the stage. There was one empty seat in the front row. I took it.

Comedian Tom Dreesen warmed us up, and then it was post time. The Voice was back.

Sinatra performing

Looking fit and masterful, Sinatra glided through “All or Nothing at All,” “It’s All Right with Me” and “Autumn Leaves.” His fifteen-song set included favorites like “Mack the Knife,” “Where or When,” and a Sinatra-esque treatment of George Harrison’s “Something.”

Midway through, he had the lights turned up to acknowledge friends in the audience, most notably a New Jersey resident transplanted from St. Louis: Yogi Berra, with wife Carmen.

Coming down the homestretch, he slowed the pace with a melancholy “It Was a Very Good Year,” turned it back up with “The Best is Yet to Come,” and closed with his favorite saloon song, “One for My Baby (And One More for the Road).”

Sinatra seemed to truly appreciate the standing ovation. He knew that everyone knew the circumstances that led to his homecoming. He basked in the adulation, and then was gone.

Sinatra Concert - retouched

I twisted out through the crowd and in a few minutes found the main dining room. I was escorted to the back, to a smaller private area with several tables set for four and one larger, rectangular table for eight—where Francis Albert Sinatra was already seated at the head chair.

To Sinatra’s right was a businessman-type to whom I don’t recall being introduced. Steve Wynn was to Sinatra’s left. In the two other seats on the right were Jim and Jamie Michelson. Adjacent to Wynn was Barbara Sinatra. I took the seat next to her, and we proceeded to have dinner like old friends. Show biz people are like that.

Frank seemed fatigued, understandable having just come off the first of two shows, and two months shy of his 70th birthday. But that wasn’t it, as Sinatra himself described.

In the previous five days, Frank had lost three of his closest friends. On October 6, composer/arranger Nelson Riddle died. Then, on October 10, Yul Brynner and Orson Welles passed away. Frank was godfather to one of Welles’ daughters.

The tone of the meal became rather glum. At one low point—and we were now clearly out of high points—Steve Wynn turned to my boss and said, “So Jim, tell us why you’re here.” His timing was lousy.

“Well, Frank, we were just wondering if you’d be interested in doing an ad for our client, Canadian Club.”

“What! And have the Jack Daniel’s people cut me off?”

Frank got a laugh from the table, and it was a nice relief for everyone but the Michelsons.

“I appreciate the offer,” Frank continued, “but I have a real long affiliation with those guys in Tennessee, and I’d hate to lose it.”

And that was that.

As if on cue, the waitress brought over a dessert tray, with a scrumptious selection of tarts, mousses and cheesecakes.

Now bear in mind: I hadn’t said more than six words all evening. Jamie Michelson and I had sat there smiling and eating, smiling and eating. But the meal was winding down, and I decided not to leave the table emptyhanded (we were in a casino, remember?). I pointed at the tray and spoke directly to Sinatra.

“So which do you think they sell more of—the cheesecake or the strudel?”

The table went silent. It seemed like the whole room did the same. And then Sinatra smiled. He smiled.

“It’s a line from Guys and Dolls,” I explained to everyone but Frank. In the 1955 film, as gambler Nathan Detroit, he’d said the very same words to Marlon Brando. I smiled back and said to him, “I played Nathan Detroit—in Detroit. In community theatre.”

“Sue me, sue me, what can you do me.” As Nathan Detroit in a local production of Guys and Dolls, I had at least that much in common with Frank Sinatra.

I don’t remember who spoke next, but it didn’t matter. Frank Sinatra got it. And he smiled.

Soon after, he said he had to get ready for the second show. He pushed back his chair. As he rose, so did four customers—two men at the tables on either side of us. But as I instantly realized, they weren’t customers at all. They were big. They were burly. They were bodyguards. And in seconds, they were all out a private door leading backstage.

Evening over. There were no photographs, no autographs, no proof it ever happened. But I know it did. And now, so do you.

Ron DavidMy dear colleague Ron David wrote about the many notable people he’d encountered during his own years in advertising and marketing. He called his book, But, I Never Met Sinatra.

Well Ron, I did meet him. I ate with him. I even made him smile.

And I did it … myyyyyyyyy waaaaaaaaay!

7 thoughts on “The Time I Made Sinatra Smile

Add yours

    1. Thanks so much once again for your wonderful support! Start spreadin’ the news! Share with your friends using the social media SHARE buttons at the end of each story. Up Next: Billy Crystal.


    1. Thank you, HR for your great support. Start spreadin’ the news! Use the SHARE buttons at the end of each story to tell your friends on social media about KatzTales! And come back soon to learn about the Billy Crystal connection.


Leave a Comment

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Create a website or blog at

Up ↑

%d bloggers like this: