Frank Sinatra: where the love began

In January of this year, I was in New York City, searching for musical souvenirs from the golden age of crooners and big bands. With its rich history and still-thriving jazz scene, New York felt like the perfect place to ask every jazz musician I met one simple question: “What comes to mind when you hear the word ‘crooner’?” And every single one of them answered: “Sinatra.”

It’s no coincidence. Frank Sinatra set the standard—not just with his voice, but also through his style, timing, stage presence, and even his way of life. The one and only Frank Sinatra is where my love for crooners truly began. He was the ultimate role model for Robbie Williams, whose album Swing When You’re Winning infected me—permanently—with the swing virus. What followed was a lifelong journey through the rich musical history of the crooner genre.

These days, the only way to take a picture with Frank Sinatra is next to his statue in Hoboken, New Jersey.

Sinatra was born just across the Hudson River, in Hoboken. It’s a place I visit religiously every time I’m in the Big Apple. And his spirit is still alive there—through Sinatra Park, Sinatra Drive, the Blue Eyes Restaurant, murals, statues, and even an old-school Italian diner called Leo’s Grandevous, covered wall-to-wall with Sinatra photos, clippings, and artwork. The man’s presence lingers.

He began his career in the 1930s and grew into a global cultural icon in the decades that followed. Inspired by Bing Crosby, he discovered the power of singing intimately. By using the microphone as a close companion, he invited you to hang on to every word. Sinatra brought intimacy to an era of grandeur. He didn’t shout for your attention—he whispered. And that’s exactly why people listened—then and now.

His music is a masterclass in phrasing. Listen to I’ve Got You Under My Skin or One for My Baby, and you’ll hear how every word is carefully placed. Even in live renditions of Send in the Clowns or All or Nothing at All, you hear his brilliant timing and his deep understanding of what the song is truly about. He wasn’t just a singer—he was a storyteller. A man who, with full confidence and authority, could pull an audience into an emotion, a mood, a scene. That gift is why so many people across the world still love him to this day.

What makes Sinatra so unique is how timeless he remains. His influence is audible in every modern crooner—from Michael Bublé to Harry Connick Jr.—and even in artists outside the genre. Whenever I’m in the studio, I sometimes ask myself: “How would Frank sing this?” The answer? “The way he felt it.” Conclusion: follow your heart in everything you do—and do it your own way. That’s what Frank did.

Want to hear more from the man who started it all? Check out my Spotify playlist 'The Return Of The Swing', filled—of course—with plenty of Frank Sinatra.