Monty Alexander, nominated for best reggae album for ‘Harlem-Kingston Express Live!,” arrives at the 54th annual Grammy Awards in Los Angeles, California, February 12, 2012.

It all started happening for Jamaican pianist Monty Alexander in 1961 when he moved to Miami.

In1962 he started playing in the clubs, bars and saloons.

“To some very colourful folk, as you might say,” he said.

“It was one night that Frank Sinatra and his good friend Jilly Rizzo come into the club to just hang out and have a few drinks.

“They heard me play and one thing led to another and I ended up going to New York. In the summer of 1963 I was playing at Jilly’s*, definitely the most ‘in’ place to go to because Sinatra used to hang out there when he was in New York City, being ‘The Chairman of the Board’ and all the showbiz people and celebrities used to come there.

“I was one of the pianists who used to play, and on some occasions I had the great pleasure of accom- pany ing him. I was a kid – 19, 20, 21 – but somehow I was capable.

“It was a most memorable time and I have such fond memories of being at Jilly’s.”

I asked if he was nervous.

“Absolutely, but I had a great bass player, Bob Cranshaw. I don’t read music so I have to use my ears. I knew the songs of Sinatra such as I’ve Got You Under My Skin and I Get a Kick Out of You, but Bob was leaning over and saying: ‘G, D, B flat’, and I pulled it off because I’m instinctive.

“All I know is Sinatra turned around with a big smile. That was it. He was one of those people who inspire you, he would come over and say things like: ‘Keep swinging kid’ or ‘You’re swinging’ or ‘ You’re grooving’.

“I met Miles Davis at Jilly’s. Miles dug my playing and he had me come over to his place and hang out. It taught me confidence because half of the stuff is being confident so that when you play ‘that’ note on the piano or trumpet, it’s the right note, not another note, but ‘that’ note, which comes only from a sense of security, and it really helps when your heroes tell you to ‘keep going’.”

What was it like playing at Jilly’s?

“Well, I thought life would end, because it can’t get better than this.”

What about Joy of Jazz and coming to South Africa?

“I am so looking forward to coming to South Africa. I will be bringing my combo, which I call the Harlem-Kingston Express, which is one way to describe what I’m doing.

“I incorporate a classic rhythm section of great players and it includes the fantastic bassist Hassan Shakur – we’ve been playing together for 35 years – and a wonder- ful swinging drummer, Obed Calvair, who is of Haitian descent, plus a rhythm section from my native Jamaica – out-and-out reggae masters who play the rhythm.

“This combination interacts with each other and I trade up with them. The piano is indeed the centre of everything because I’m talking as we go. It’s never less than an exciting musical experience for all of us. We come there to make it feel good and we hope the audience will enjoy it just the way we do.

“I am embracing my love of American classic music such as Ellington, Basie, Charlie Parker and Erroll Garner with my native Jamaican rhythms, reggae and ska. So we just have a big ’ole party.

“My greatest hero was Louis Armstrong. I’m a messenger of goodwill. When I play I try and make it right for me and everybody else, from straight ahead trio jazz to a combination of Jamaican music.

“It’s a great moment in time, this is my 50th year as a professional musician, and Jamaica is cele- brating 50 years of independence. I’m so thrilled to be invited to South Africa to share my music and to bring this new 2012 version of what I’m doing.

“I looking forward to playing for the people there and taking them uptown and downtown, meaning Harlem and Kingston, and making a statement of all things good about life.”

* Jilly’s, the famous watering hole, was on 52nd Street and owned by Jilly Rizzo. Only Sinatra records were in the juke-box and the walls were plastered with pictures of Ol’ Blue Eyes and memorabilia. I have a Jilly’s glass I pinched from there.