Dean Martin: Effortless charm

I never got to see most of the legendary crooners live, but ever since I caught the crooner virus, I’ve spent hours watching footage of the greats: Frank Sinatra, Sammy Davis Jr., Mel Tormé, Nat King Cole, and Dean Martin.

In those videos, Dean Martin always seemed like he was just chatting with the audience. With a glass of whiskey in one hand, a relaxed stance, and a twinkle in his eye. He sang as if he was making it all up on the spot. Casually, often half-singing, always with a joke nearby. But don’t be fooled. Behind that laid-back charm was a razor-sharp sense of timing, musicality, and showmanship.

What made Dean Martin so special was his ability to not take himself too seriously. While many performers work hard to impress, Dean’s magic lay in doing the opposite. He laughed at himself, put the audience at ease, and could say more with a single raised eyebrow than others could with an entire vocal crescendo.

His style was relaxed, but never sloppy. Lighthearted, but always on point. He could half-sing, half-speak a line, and it still landed. You believed him. Dean trusted his charm, his spontaneity, and his intuition. And that disarming ease is what made him unforgettable. He had the talent to make entertainment feel human and pure.

During his years with The Rat Pack, alongside Sinatra and Sammy Davis Jr., his looseness became his signature. On stage, they joked, played with each other and the audience, and broke the rules on purpose. They proved that class and fun didn’t have to be opposites.

Dean’s songs like “Ain’t That a Kick in the Head”, “That’s Amore”, and “Everybody Loves Somebody” mix humor and romance, two of life’s greatest gifts, if you ask me. And that’s exactly why I still admire him so much today. The video below shows Dean Martin at his best: witty, playful, and musically flawless.

Dean Martin at his best: humor, self-mockery, and beautiful music.

In my own shows, I’m always looking for that same balance between humor and emotion. Not because I want to imitate Dean, but because I truly believe people need to be able to laugh and relax, before they’re ready to be moved in. If you can make them smile, they’ll naturally open up to the rest. You can see this in today’s crooners too. Michael Bublé, for example, has that same twinkle, that same warmth. And in my opinion, that’s his greatest strength.

That combination of humor and heart is pure magic. After shows, people often say, “You made me laugh, but you also touched me.” That’s exactly what Dean Martin mastered. I honestly don’t think it’s something you can learn. You either have it—or you don’t. And Dean? He had it in spades.

Want to hear my version of “Everybody Loves Somebody”? You can pre-order my upcoming album now, featuring some of the greatest crooner songs of all time. The album will be released later this year, but is already available for pre-order in my webshop.