An Evening of Laughter and Stories of Sinatra

Legendary comedian Tom Dreesen's captivating one-man show

Tom Dreesen, the legendary stand-up comedian who opened for Frank Sinatra for 14 years, entertains with an evening of stand-up and stories you won't hear anywhere else. The Los Angeles Daily News says it best: “Only a guy who traveled with Sinatra for 14 years and stood in the wings watching him work his magic night after night to packed houses could pull off a show like this."

This totally entertaining show has something for everyone. The Chicago Tribune calls the show "brilliant, funny, poignant!"

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The Remarkable Backstory

The story sounds like creative fiction, but incredibly it‘s true. With his family almost penniless, a young boy shines shoes in a bar in a gritty industrial town on the outskirts of Chicago while the juke box plays Frank Sinatra singing Come Fly with Me. Fast forward as the boy grows up to co-create a ground-breaking comedy duo, takes The Tonight Show Starring Johnny Carson by storm (the first of 61 appearances on the show), opens for Sammy Davis, Jr., and three years later gets the offer of a lifetime: fly away with Frank Sinatra, criss-crossing the country and opening for him for the next 14 years.

"He’s a great story teller. And nobody could tell this story better than Tom."

This is the remarkable story Tom Dreesen shares as the backdrop to his captivating show, An Evening of Laughter and Stories of Sinatra. For well over a decade, Tom saw it all — and experienced it first hand. This performance captures the essence of what it was like to share the stage — and the offstage moments — with the incomparable Frank Sinatra.

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On the Road with Sinatra

Traveling with Frank Sinatra was like being in another world, from the magic of watching backstage as Sinatra thrilled audiences night after night in sold-out shows in New York, Las Vegas, and Atlantic City, to personal moments talking about life and family into the late hours with the Chairman, who rarely went to sleep before the sun came up.

"An Evening of Laughter and Stories of Sinatra is brilliant... funny... poignant!”

— Rick Kogan, The Chicago Tribune

Tom often was a guest at Sinatra’s estate in Palm Springs, where he hung with Dean, Sammy and countless others. In An Evening of Laughter and Stories of Sinatra Tom shares one memorable story after another in rich detail — punctuated with the humor that has made Tom a comedy legend.

What advice did Sinatra give Tom before he went on stage as his opening act? What about the time Frank offered to sing for a woman after hours in a deserted bar — and she turned him down? And the time it seemed the Chairman might be nearing retirement, only to astonish the standing room-only audience in an unforgettable moment.

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Book this Celebration Today

Frank Sinatra often quipped that he was a "saloon singer," and he characterized Tom Dreesen as a "saloon comedian." Sinatra would say to Tom, "We’re a couple of neighborhood kind of guys." An Evening of Laughter and Stories of Sinatra is a personal story of those guys, a story as entertaining as it is touching.

"It was amazing how much material Tom had. It was excellent."

For any audience — Sinatra fans, customers, employees, club members — and for any event (corporate gatherings, celebrations, conferences, special galas), An Evening of Laughter and Stories of Sinatra is the perfect performance, praised for its laughter, tears and personal reflections on life. Celebrating Frank Sinatra’s 101st birthday, An Evening of Laughter and Stories of Sinatra is available now for bookings.

To book this remarkable, one-of-a-kind event, call 888.428.4646 or complete this form. We’ll promptly answer any questions you have and get your special performance of An Evening of Laughter and Stories of Sinatra with Tom Dreesen on the calendar.