From TV Screens to Times Square: Kurt Decker Finds New Life in Sinatra’s Legacy

For Kurt Decker, a nine-time Emmy-nominated television producer, life after television wasn’t a neatly charted path. It took a nudge from an old friend and a love for Frank Sinatra’s timeless music to set him on an unexpected journey. Today, Decker captivates audiences at The Playwright Tavern in Times Square, transforming Sinatra’s classics into personal and heartfelt performances.

“I wasn’t sure what my next move would be after leaving television in 2017,” Decker admits. “A friend of mine who owns a bar in Midtown suggested I do my ‘Frank Sinatra act,’ as I was known to busk at the bar. That conversation changed everything.”

Decker’s transition to music wasn’t entirely surprising given his upbringing in a musically inclined family. “Growing up in a music family gave me my legs for singing,” he says. “Although I ventured into photography and television, returning to music felt natural once the opportunity presented itself.”

Breathing New Life into Sinatra’s Legacy

In his residency at The Playwright Tavern, Decker brings a fresh energy to Sinatra’s catalog, blending iconic standards with his own unique style. His song selection process is both personal and collaborative. “Frank recorded over 1,200 songs,” he explains. “If someone requests a song I’m not familiar with, I’ll listen and see if it connects with me emotionally. When I perform, I imagine myself as the lyricist, making the songs my own.”

Decker also complements his Sinatra repertoire with hits from Elvis Presley, Billy Joel, and Tony Bennett, adding depth to his performances. “These artists round out my setlist and resonate with audiences who love more than just Sinatra,” he says.

Creating Memorable Moments

For Decker, the joy of performing comes from the connections he forges with his audience. “People often share that Sinatra’s music reminds them of moments with their parents or grandparents,” he shares. “Seeing their emotional reactions is incredibly fulfilling.”

Performing in an intimate venue like The Playwright Tavern allows Decker to engage directly with his audience. “With a wireless mic, I can walk right up to tables or even sit down and sing to someone. It creates a special, unforgettable experience,” he says.

Decker’s ability to tailor his performances extends to private and corporate events, where he reads the room and adjusts his setlist to suit the atmosphere. “Making people feel comfortable and at ease is key,” he says.

A Career Rooted in Creativity

Decker’s Emmy-nominated career in television, including stints on The Tonight Show and Saturday Night Live, has profoundly influenced his music. “Working with directors, actors, and musicians taught me invaluable lessons about live performance and connecting with audiences,” he says.

Looking ahead, Decker embraces the uncertainty of life with open arms. “The only constant is change,” he muses. “I’m ready for whatever comes next, and I truly believe that ‘the best is yet to come.’”

As Decker continues to sing Sinatra’s timeless tunes, his performances serve as a reminder of the enduring power of music to connect generations, evoke memories, and inspire new beginnings.