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Sinatra at 100: How the crooner helped launch Monty Alexander's career


Monty Alexander's SINATRA AT 100

News | Jan, 26th 2016

Ask Monty Alexander about his connection to Frank Sinatra, and he'll tell you: "Lightning struck twice."

And this Feb. 12-13, when the acclaimed Jamaican-born pianist performs Sinatra at 100at Jazz at Lincoln Center's Rose Theater with help from friends including GRAMMY® Award-winning singer Kurt Elling, he'll explain exactly what he means.

The short of it: it took two meetings with the legendary crooner for Alexander to make his way to New York and begin performing in the same after-hours nightclubs that Sinatra haunted for much of the 1960s.

The first encounter took place in 1961, when Alexander was a teenager newly arrived in Miami from Kingston. Alexander was playing piano at a Miami Beach bar when Sinatra stopped by with his good friend Ermenigildo "Jilly" Rizzo.

Rizzo owned his own club—Jilly's Saloon, at 256 W. 52nd Street—that was Sinatra's primary hangout in Manhattan. But while the New Yorkers complimented Alexander's playing, nothing came of that first meeting. 

It was later, in Reno, Nevada, that Alexander made a more meaningful connection. Rizzo and Sinatra checked out Alexander's set at the Thunderbird Hotel and encouraged the young player to come play for them in New York. 

A few days later, Rizzo bought Alexander an airline ticket and soon the pianist was a regular at Jilly's, playing for a who's who of entertainers and musicians. As Alexander describes it, he had entered “a brand new world, a brand new life—and I’m making it with music.”

Alexander met Miles Davis and Count Basie at Gilly’s. He quickly became a fixture on the New York scene, playing frequently at the Playboy Club as well as Jilly's.

Alexander and Sinatra were friendly for years, last seeing each other when Mike Tyson fought Mitch Green at Madison Square Garden in 1986. Sinatra was always “very generous, very kind,” Alexander says. 

The pianist will try to create a similarly genial vibe with Sinatra at 100.He wants the show to feel like it's "Jilly’s at Jazz at Lincoln Center.”

And as the shows will attest, it might not have been so much about luck or lightning striking as it was about innate talentfor Alexander and his career's ascent to perhaps the most swinging musical testing ground of the early 1960s.


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