Jamaica to New York: Monty Alexander's Wild Ride

Performances and Artists

It took two encounters to seal the deal, but the deal changed Monty Alexander’s life. Those two meetings, with Frank Sinatra and Ermenigildo "Jilly" Rizzo, brought Alexander, Jamaican-born pianist, into a new world of music among show business giants. And that new world, Jilly’s Saloon in New York City, was the East Coast court of Sinatra.

Here’s how it happened: Alexander had moved to Miami Beach as a teenager and began playing a local club in a lounge next to the room where Duke Hazlett, a Frank Sinatra tribute artist, was performing. Sinatra, Jilly and Jilly’s wife came in to see Hazlett and saw Alexander. Jilly’s wife told Alexander he should come to New York and perform at Jilly’s, but nothing came of it.

“About six months later, I happened to be in Las Vegas playing in an old-time band, led by a man named Art Mooney, and in walks Frank Sinatra and Jilly again and they saw me. Two days later I got an airline ticket,” remembered Alexander.

He performed at Jilly’s for three years (and frequently at the Playboy Club) and expanded his world to include jazz giants Milt Jackson and Ray Brown. He became part of the New York music scene and jazz world and was accepted by other greats, including Duke Ellington, Count Basie, and Miles Davis.

Alexander’s growth and versatility are the keys to his success for decades, with collaborations that span multiple genres, styles, and generations. He has worked with Natalie Cole on her Grammy-winning tribute album to her father, Nat “King” Cole, performed George Gershwin’s “Rhapsody in Blue” under the direction of Bobby McFerrin at the Verbier Festival in Switzerland, and recorded a Christmas album as the featured pianist with Tony Bennett.

But it is Sinatra and the nights at Jilly’s that remain one of the integral threads in Alexander’s life. Sinatra was always “very generous, very kind,” Alexander recalled. He is bringing his sense of that time and place, performing interpretations of Sinatra’s songs and sharing memories in “A Night At Jilly's, Sinatra At 100 With Special Guest Clint Holmes,” May 13-14 at Cabaret Jazz.

Jilly's Saloon was located at 256 W. 52nd Street in New York City. The Smith Center’s Cabaret Jazz is located at 361 Symphony Park Avenue in Las Vegas. But for two nights in May, thanks to Monty Alexander, both addresses (and both worlds) are in one spot.