Dean Martin, Bing Crosby & Frank Sinatra – The Oldest Established: When Legends Shared the Stage for a Laugh

About the Song

When Dean Martin, Bing Crosby, and Frank Sinatra joined forces, it wasn’t just music—it was magic. And in their spirited performance of “The Oldest Established (Permanent Floating Crap Game in New York)”, they brought Broadway flair, Vegas timing, and old-Hollywood wit into one unforgettable moment.

Originally from the 1950 musical Guys and Dolls, “The Oldest Established” was never intended as a solo showcase. It’s a character-driven show tune—fast-paced, playful, and filled with tongue-twisting lyrics about the backroom dealings of New York gamblers. But when you hand that kind of material to three of the most charismatic entertainers of the 20th century, it becomes something even better: a masterclass in charm, timing, and camaraderie.

Dean plays it cool, Bing delivers with that effortless baritone warmth, and Frank—always the ringmaster—drives the rhythm like a seasoned bandleader. There’s banter, there’s laughter, and above all, there’s joy. You can tell they’re having fun, not just performing a number, but poking fun at each other, leaning into the rhythm, and turning a Broadway novelty into a Rat Pack-style celebration.

While this rendition may not be the most polished recording from any of their catalogs, it doesn’t need to be. Its value lies in the chemistry—three old friends sharing a stage, a joke, and a moment in time. For audiences who remember the golden age of variety shows, or who grew up watching these gentlemen in black and white on TV screens, this performance is pure nostalgia.

“The Oldest Established” might be about a “floating” crap game, but what’s really on display is something solid and lasting: the timeless appeal of three legends who never took themselves too seriously—and always knew how to leave a crowd smiling.

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