‘Upliftment’ from Jamaica to Jilly’s: An interview with the irrepressible jazz icon Monty Alexander

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Jazz great Monty Alexander.

“The pride in playing a song and making people happy was the most powerful thing I could imagine because the gift of changing people’s minds and attitudes is so powerful. We are just entertainers and we have a way to affect people in a positive way. That is what I do when I play. My gift is to turn negative into positive.” – Monty Alexander 

There is talent, and there is a force of nature. Jamaican-born jazz great Monty Alexander  is among the latter. In his implausible ascent to the top as an international jazz icon, the award-winning and Grammy-nominated Alexander, decidedly chose the road less traveled. With more than 70 albums to his credit, Alexander has performed alongside a dizzying number of fellow prolific musical artists including Jamaican producers Sly and Robbie, master guitarist, and composer Ernest Ranglin, vibraphonist Milt Jackson, as well as The Chairman of the Board himself, by personal request, Frank Sinatra.

Being an avid fan of jazz is of no consequence. Alexander’s progressive chords transcend classification. Calypso, ska, reggae, gospel, blues, boogie-woogie, classic R&B, and even a little funk for good measure. An array of multi-genre musical masters long past, copiously channel through his fingers. But, it’s not only listening to Alexander perform, it’s watching him tap into his unending personal reserve of infallible inspiration that underscores his musical aptitude. 

Alexander’s rendition of Fungii Mama backed by the Harlem Kingston Express conjures images of blue skies, languid palm trees, white-sand beaches, and curvaceous barefoot, brown-skinned women with sparkling wide smiles and fluid bodies, instinctively facing the sun, clenching their cotton skirts in unabashed hip-swaying surrender. Count on Alexander, an avid classic film fan, to intertwine Gershwin’s “I’ve Got Rhythm” into its calypso composition, then seamlessly return to the song’s origin. His translation of  “Bob Marley classics” are refreshing, some immediately identifiable, some injected with gospel undertones and blues idioms, others with a slant of Rachmaninov or Chopin -but it was his unique jazz “swing” that caught the ear of fellow musicians allowing for his inconceivable journey. As Alexander states, “The piano became my passport.”

Jilly Rizzo and Frank Sinatra.

It’s no wonder that at the age of 19, after Frank Sinatra and Jilly Rizzo witnessed Alexander’s performance for the second time, Alexander found himself performing where the underworld met the elite, at New York’s inner sanctum, Jilly’s saloon. Notoriously frequented by gangsters, Jilly’s was a favorite hangout of Frank Sinatra, exclusive musicians, and Hollywood’s Golden Age celebrities including members of the Rat Pack, Miles Davis, Count Basie, and Judy Garland. 

The following is a Q&A with Alexander. His latest album, “Wareika Hill Rastamonk Vibrations,” was inspired by Thelonious Monk. If the esoteric artistry of its cover seems familiar, know that it is the visionary work of natural mystic Rudy Gutierrez, the same illustrator who earned multiple commissions for the shamanistic covers of Santana’s albums and CDs.

CC: What was different about your home life that fostered who you were able to become? 

MA: Most West Indian parents are not scheming with their child to cut school and go see Louis Armstrong. My father took care of my family but he had a little bit of good mischief! He saw his son, little Monty, being so happy with this music thing, he saw the delight that came over not just me, but other people when I was playing the piano, and he knew that I was just such a fan of Louis Armstrong. Louis was going to come and perform in Kingston, and I must have been 11 at the time. I did everything in my power to convince [my father] to drive from Kingston to Mandeville where I was in boarding school at the time. I had braces and I figured out how to make the wire stick into my jaw so I would have to go see the dentist. I could’ve put it back in myself but I told my headmaster I had to go see Dr. Machado in Kingston and I timed that doctor’s visit to the Armstrong concert. I couldn’t miss it – I couldn’t miss it. One thing led to another and I made the plans with my dad and he indeed came to the school and picked me up at the right time. We drove into Kingston. Two hours later, we were at the dentist’s. He suspected I was up to no good, and he gave me that little paper that said Monty Alexander came to my office. We got out in time and drove to the theater right in time to see Louis Armstrong and that was a great moment. The thing about popular music and most people in entertainment is you have to have a little rebel in you to do what you need to do.

Louis “Satchmo” Armstrong

CC: You had a different relationship with your father than most.

MA: I know that, yea. My mother was a real disciplinarian – far more than he was; my father was responsible, he was like my friend, my partner in crime. In the middle of the school week when I should be studying and I wanted to go to the movies he went to the movies with me. When I think of it, I think of how unusual it was and I get a big smile! I had to respect the right and the wrong, but my father would say, “What’s the harm in Monty going to the jam session and playing music with those guys?” Whereas my mother wanted me to study and maybe one day go to the piano teacher so I could be a classical pianist and go to the Royal Academy in London – which I also rebelled against and from the moment she said that, I was turned off. What jazz and popular music were about is “I’m going to do it my way,” not the school book way, and that’s been pretty much how I operated and had a career. I made over 75 albums, I’ve played with the greatest jazz musicians in the world. I kept the Jamaican thing intact, but that had to do with what shaped me I believe.

Thelonius Monk

CC: How did your family, especially your mother, respond to your growing fame, and to meeting people like Sinatra, Dizzy [Gillespie] and Thelonious [Monk]? 

MA: She wasn’t tuned in to the American jazz world. She knew Frank and Nat [King Cole], but she didn’t know who Thelonious Monk was. She knew calypso musicians and songs but she didn’t know the inside stuff. My mom came to America to get away from what was not going well in Jamaica and we went to Miami, FLA, but me, slipping into this amazing world, this whole environment, this world of jazz. I just liked music. I didn’t think of jazz because I knew these jazz people were rebellious to a point where they were self-destructive, but a good side about my mother and father was the discipline. I received strong discipline to stay away from harmful things, like when I saw the musicians slipping into cocaine and shooting heroin in their arms and I’d say “What the hell is that?” I really had a combination of what the good book said and what my mother said, so I had that in me.

Jamaican flag.

When you talk about the West Indies, they used to say the British West Indies so you’re talking about discipline and manners and proper behavior. I got a dose of that, so being a talented mimic of certain things I knew how to eat properly with a knife and fork and address my elders. When I was going into this recording around Thelonious Monk’s music I found that he was brought up around West Indian people. He was an African-American kid from North Carolina but at five years old his parents brought him to San Juan Hill (located behind the area now known as Lincoln Center) which was a poor area and a lot of the West Indians lived there. Another thing about the discipline, it came from fear because we are in this new land of America, these buildings and these rich white people, and I could slip in and out of all these different worlds. Some of our families were disciplined to a fault but I was this rare exception. I’ve always been blessed all my life, this lucky guy, I don’t understand it but I’ve come this far, something to do with this free-spirited attitude.

CC: I haven’t seen an interview with any negative statements about how you were treated. Can you recall a time when that happened?

MA: If it did, I must have been carrying some kind of Teflon. This is a great question. I should do some more research on why I had this gift to, first of all, imagine that everybody that’s good, there is something bad in them and everyone that is bad, there is something good in them. I won friends because I played a little tune and made people smile. The whole history of entertainment in the movies, films and music, you see anybody of color, they have to tap dance and blackface and all these things to be an entertainer. I’d read a little scripture about how we are all created equal and something about music would equalize everything. You become like Bob Marley, “One Love.” I believe that this music gift had the power to bring people together. I’m a musician but I don’t play what is on the paper. Here is where movies came in; by going to the cinema and falling into dreamland. I play what is in my dream space. I dream the music. I respect the classical great musicians but a lot of them are in a straight jacket. 

CC: When you were very young jammin’ with musicians, did you ever have a glimpse of your destiny?

MA: Wow! I didn’t really think it could happen to me, any kind of glorious thing, because I’m in Jamaica and, you’re not stuck, but this is all there is to this. You have beautiful beaches, people dancing and music. It was because of my mother and her determination to get away from a situation that could have become worse and worse that she really saved the day. But I was just the classic case of a guy living in a moment – today is the last day maybe, and I’m not going to be a goofball and throw my life away, but I am going to sneak out of the house and play with those guys at that little bar and jam sessions. From an early age, I just had this attitude that now is the time and maybe that is why I didn’t have a proper education. I didn’t graduate but my story is not unlike other entertainers of my time. I mean Frank Sinatra didn’t graduate, Nat [King Cole] didn’t graduate, Roy Rogers didn’t graduate, all these people that were celluloid heroes of the screen, you realized later on in life they were just a mess. Charlie Chaplin – everybody had a terrible background and the music and the entertaining became the antidote. I was very fortunate to be able to press on and bring a smile. I tried to find that balance between don’t sacrifice your self-respect but at the same time, find a way to get along with other people. Where it’s that common bond, and I think that is something I do automatically.

CC: You once stated, “I didn’t do it; it happened. When the quarterback throws you the ball, don’t throw it to the sidelines, go for the touchdown.” How did it happen? Why you?

MA: That’s a good question. Part of it was a magical ride. I came up from Jamaica and had no idea what would happen next, that music was even something viable. My mother, who was on the discipline side, wanted me to continue school and get the degree and hopefully like most parents, wanted me to be a good lawyer and things like that, and I didn’t have any of that in my being. I continued what I was doing…which was to walk the streets and look at the big tall buildings in Miami Beach and, wow, these are amazing people who had money and they were successful. The piano was my passport. Hopefully, I wasn’t misusing the gift because I don’t even know how it happened. It was a gift, I had this passion to sit at the piano.

My passion would come out when I was playing the piano. I saw what would happen to a room of people, how it could turn their disposition from negative to positive because it’s music. That’s what Louis Armstrong did when I saw him on the stage, and same with the calypso musicians. So I had this gift but I didn’t ever get smug about it – like I’m so special… I never had that. I had humility about this precious thing that became my passport. And I think Sidney Poitier who, by the way, I loved and admired everything about that man, he brought his pride and his dignity, and Dr. Belafonte, another man who’s anger manifested itself in being such an important part in the civil rights movement, would say the same thing. There is a humility that goes along with it. I believed that somebody up there liked me and had this special hand over me…I always said that. Even though I wasn’t deeply religious I always felt that. One year after I came from Jamaica, I’m playing all over Miami and, “Hey kid, that’s great,” and one of them is Sinatra! He saw me playing with his friends and that is how I ultimately came to New York City when I was 19 and I am playing in this club with all these tough guys and boozers and heavyweights in show biz and there I am, where you don’t even see a Jamaican. I played off and on for two years at this club named Jilly’s in 1963 when I finally came there. I remember thinking how is this happening and it was because I could play the piano, and people would say “Hey kid, you are really swingin’!” A year and a half ago I was in Kingston not knowing what’s going on.

CC: What was it like to play for Sinatra at 19-years-old? 

MA: Well, I’ll tell you right now even today so many years later I can’t even put it into words. The only word I have these days to use when I talk about certain things, about music that I have experienced, to chase that yesterday happening is a one-word. Magic. I use that, and that dispels a lot of technicalities. It’s so nice to know Constance, that you are on a wavelength because what happens a lot is that people want to talk to me, but they don’t have the reference that you have. The main thing is to say it was a dream world that was real.

CC: I believe that great artists tap into the unseen and essentially channel their craft.

MA: I hear you. I hear you. 

CC: So, what makes an icon? What separates a Sinatra, Ella or Nat from the rest? What is the difference between a natural and a well-learned student? 

MA: About the whole idea of this whole magical thing, that some folks have and some folks don’t, and there is this wonderful old scripture that applies – many are called but the chosen are few..there you have it. So some of us, we strive to do this thing and it brings us such delight. It’s infectious but it’s so strong and so wonderful. I mean, what is it that made “It’s a Wonderful Life?” This thing that is all celluloid, and a smart director, and James Stewart? You know there is something that you can’t put your finger on, and Sinatra, Nat, when I think about those men who just used their voices and sang these lovely melodies that you don’t hear anymore in the world. I grew up on Frank, Nat, Bing Crosby – those men had a driving combination of passion for the song as well as discipline to sing the right notes and bring some kind of charm because, when Sinatra sang, he was telling a story. He was like Laurence Olivier, a thespian. He had powerful delivery in his song but he had different stages. When I was around him, [Sinatra] he was in that “drink a lot until five A.M. in the morning,” stage. I was two tables away from him sitting there with his buddies and accompanied him on occasion. These people are just larger than life, they stick out. My greatest hero is Muhammad Ali, and he is doing it all because of that inner thing within. His brother didn’t have it; his mother and father had no idea what it was, and all these things came together in those few years and he became this one-in-a-trillion human being that the world hated. A lot of the naysayers, the hypocrites, they all turned around loving him and I loved this man. I met him and shook his hand in Miami Beach. FL, when he was Cassius Clay, so all my life I followed the example of what would Ali say, as one of the people walking the earth and how would Nat handle this? Those guys became my heroes, they did.

Monty performed at Minton’s Playhouse, Harlem from 1966-68.

CC: How important is intuition in your music?

MA: It’s the whole thing, because, if you ask me what was that chord, I have no idea! I’m serious! C-minor, all that type of talk, I go blank. That is why it was a turn-off for me whether it was algebra, trigonometry, it was a turn-off – BAM! I would lose it. But if we did something in the arts? It was the same thing for manuscripts, reading music, if they tried to put paper in front of me, I’d say I don’t read music. That part of my mind retains that information and then turns it into what I do, which is called inspiration. I couldn’t connect it, so consequently, I did the irresponsible thing. I didn’t want to go to school to learn how to read it. It’s all instinct and inspiration. The word inspiration means the spirit within, and you can have the inspiration to come into your being and seek it. Seek and ye shall find. I did that from an early age. I literally looked in the mirror for inspiration. If I’m thinking right before I play, I pray. That magic, you can’t put your finger on it. To this day, Constance, I have no idea how I came this far. 

CC: How do you select people to play with?

MA: I don’t go too far out of my way, destiny kinda puts us in the same place. I like them. We have a comfortable understanding. Laughter, a joke, and I could just transfer to playing the notes and the person was competent. They had a certain instinct and we had a musical good time. It’s hard to put into words but when I met this great man in my life, one of the treasured musicians, Ray Brown, the great bassist who was inspired by Duke [Ellington]. We met. He liked me and I liked him. We didn’t even really play together and one night I went to LA to see him play and there weren’t people really listening that much. He was Ella Fitzgerald’s first husband. No one was really paying attention, but I was there just thrilled to be in the presence of those guys, and the piano player who was going to play the last song was at the bar, drunk. He couldn’t lift his head up, this great musician but an alcoholic. I saw the piano and they went to play the last song for the night. The drummer picked up his drumsticks, Ray picked up the bass and the guitar player picked up his guitar and started, and I just kinda got over my trepidation. All right, Monty, you’re gonna walk over to him and cross that barrier because once you cross that barrier and play music together you become musical knowing (understanding each other musically) – it was kind of a feeling I had, and a passion and I said to Ray Brown can I play a tune? He could’ve looked at me that moment and been a smart musician and said, of course not! But he said c’mon, and within four bars of whatever that song was – let me tell you-the sky opened up!

Monty Alexander and Bassist Ray Brown.

The next thing he was hollering joy, having the time of his life! Why? Because of this little Monty guy, and we just became like one, swinging with all these musician guys! Bob Marley said, “One good thing about music when it hits you, you feel no pain….” and he was kinda humdrum with his other musicians but here I come with my passion and fun and we got off the bandstand and we were all happy, and he said, “Where are you going to be? What are you doing in June?” This is like January and he said, “I want you to play with me and Milt Jackson.” That was how the door opened and the next thing I’m playing with Milt Jackson, next thing you know I’m playing with Dizzy Gillespie, Sonny Rollins, like a club of people, a private bunch of people, and I was allowed to be in that. I had skills. I was able to slip into all these genres. When I first ran into these jazz Bebop guys I saw guys who were all one-track-minded, ”Hey this is the music, that stuff is corny over there.” To me none of the music was corny. I loved country and western, old-time blues music, classical music, Rachmaninov, I loved all. Dizzy [Gilespie] once told me his favorite accompanist in the jazz world was Nat [King Cole]. I wanted to be one of the guys as well as one who was striving because there is always that invisible barrier between successful guys and the other guys who are trotting along.  It was a struggle for me because I felt so friendly toward the “cats,” as we used to say. If you were doing good you almost felt guilty that you were doing well. Thank God, I always had a job playing music. 

CC: When you are performing on stage does the audience exist? It seems like it’s you and the band and just having a good time.

MA: That’s what it feels like for me too because I almost need people to join me in my efforts. That comes with that positive attitude, nobody smugly saying I’m greater because I do this and that. No, no. We are humbled because of this gift. I have to have different combinations of musicians. My main ingredient is bass and drums, people of goodwill who I seek. These guys that have a weird attitude I run away from like the plague. I’ve been absolutely amazed by so many musicians, not the famous guys, the accompanist that would support, because they would have such a ball with me. Then if I came with the trio the audience became the fourth member because I knew they were there. It’s hard for me in a recording studio to make the music that would fly, to go to that other place where you can’t explain it. There’s no people. It’s not that I am an egomaniac but people aren’t there to be celebrating this experience with me. I just always was able to have people with me who were catalysts and guys who enjoy going on the ride as well because when you get on the bandstand with Monty Alexander you’re gonna have fun, man! You’re going to get your $20 worth-but to this day I can’t explain it, what it is, but it’s my joy! I like to use the word “upliftment”-uplift people’s outlook, and I saw that from my heroes back in the movie theaters, Sinatra and all these great people.

CC: It’s as if you lived a dream you didn’t even know you had.

MA: You said it. That’s exactly right.

CC: I saw you in a commercial for TCM (Turner Classic Movies).

MA: The first time I got involved with TCM activities I went on the second of the cruises and Debbie Reynolds was a guest and she talked about this, that, and the other. It was so marvelous, it was so great to be around her and those memories of Singin’ in the Rain and those songs which I loved. A big part of our game here is old film. I started meeting the TCM people. I met Mr. Robert Osborne. I got to know them [TCM staff] and it unearthed my memories of old film. Humphrey Bogart, film noir, and I would sit there, loving it, loving it, loving it! It would bring back Kingston Jamaica in my mind watching those films.

CC: Do you ever play any of your songs the same?

MA: Well that is easily explained, but I have about three different versions of explaining it. The reason is that I fell into a wonderful thing, because when I sit at the piano and I’m going to play something, somehow it’s like if you see a jar of jelly beans, are you going to pick the orange ones or the blue one or the green one, all these different flavors, and it seems I have all these flavors that I can play. I can pick orange or blue or all these different colors I like and I play that color. I will just go like it’s the first time I ever played the piece. I have a good disposition and I don’t let negativity invade me. Not because I’m so clever, it’s because if I played it great that last time, I don’t want to play that again. The problem is, I can’t remember what I played so I have to play something different, and if I try to repeat myself then it’s going to be “flat.” Don’t play orange this time, I played it the last time, play green, and I start on a different key. Apparently, something I could do naturally was play in all the keys of the piano. No one knows how to play in the key of “B” but somehow I picked up on how to play in the key of “B,” so I would just do something different to surprise myself. I’m always surprising myself. The moment dictates, the mood dictates and that’s where you’re going to hear different things. Most times and when Sinatra talked about going into the studio, if the director didn’t get it and the cameraman didn’t get it on the second take he’d say, “I’m outta here!” With a guy like me, the magic happens on the first take, the second take. So your whole attitude is like, now is the time.  When I play, it’s the first time and people come there [to the concert] and-I hope he did it like he did it the last time. Nope! Forget it! It ain’t gonna happen. I heard it on the record you did this…NOPE! 

CC: Let’s talk about your latest album Wareika Hill Rastamonk Vibrations. There is gospel, ska, Lovers rock, and of course, Monk and the artwork is beautiful.

MA: Thank you so much. It all happened through good folks, serendipity and a man by the name of Hollis King who was an art director for Universal Records, a Trinidadian by birth. He has done a lot of art directing for, among others, Natalie Cole, Diana Krall. A very accomplished, down-home brother. Through him I met Geoffery Holder. Hollis and I became friendly and he introduced me to Puerto Rican-born Gutierrez who did album covers for Santana and that is what we see. I always love bringing people together when I’m playing. In the back of my mind, I like to see those kids over there with dreadlocks hanging out with the Park Avenue folks. It’s part of what I do.

The whole idea was of bringing Monk together with the roots, the Jamaican, the West Indian, and Monk’s music, which is quirky. To the real deep jazz people, he’s an icon because he came up with these quirky little songs. Monk was definitely super, super, special. He wasn’t a great pianist by any means. He had a way of playing, plunking along and I loved it because it was like a child’s thing. There is something about Monk that, I just smile! Monk had a serious look on his face making all these childish tones. When I made that record, I said you know what, I hear some calypso rhythm in the song and I decided to not just suggest them but I decided to go deep. I brought in the Rastafarian experience some of those tunes I took the Nyabinghi rhythm of Rastas who were up Wareika Hill which was right next to my house-who I heard when I was a kid. Those drums are so infectious and it’s simple, it’s primitive and soulful. It’s down to earth and I’m the same guy still loving Nat King Cole singing ballads. So I brought that in and I played one song on the record that is an old church hymn. My mother’s favorite hymn called “Abide With Me” I brought the Rastafarian drums with it, just playing that beat with a piano version of it and then, the other tunes, I brought them to a Jamaican experience, and the whole thing was just made to order. I love doing it because I was bridging people together. 

I’ve been doing talks on Youtube. I call it “Reminiscing in Riddim.” I just go at it if you ask me a subject like tell me about Sinatra, I can tell you a whole lot. I could go on and on and on about life, Jamaica’s life before Bob Marley came to town. It’s a lot of reminiscing. 

CC: Any words for the 11-year-old Monty? Any words for the younger generation?

MA: At that early age somehow the piano became my favorite toy. You can’t force it because usually when you force a kid it’s a turn-off. With me, I always had fun from the get-go, so find your fun. The thing is, I would just go to the piano and bang away. I’d pick out the melodies and if you like a song play it with your little index finger. Play, and the fact that somebody can do that, gives you a delight! Gee, I just played “Mary Had a Little Lamb,” so find those little things that give you a smile and that’s just what I did. Next thing, I was grooving and people are clapping their hands and they like it and that’s all I know. If I had to tell something to 11-year-old Monty, just keep doing what you are doing. Of course you are going to have to beat back the negative people that are going to say things to turn you off, or hurt your feelings, and you have to know how to deal with that. Run like hell from the negative and boost up your confidence. You don’t want anyone to steal your joy. When those dark feelings come around, I have a great conversation in the mirror with myself.

Check out Monty Alexander’s website for tour information


About this Author

Constance Cherise

Constance Cherise is a freelance writer and contributor for Turner Classic MoviesSee her work here.