There is a moment on almost every Monty Alexander record where the jazz piano trio stops behaving like a jazz piano trio and starts behaving like a Kingston sound system. That moment is the whole point. Fifty tracks deep, this is the sound of a man who never asked permission to be two things at once.
The pianist who brought Kingston to the Carnegie stage
Monty Alexander was born in Kingston, Jamaica in 1944, and by his teens he was already gigging around the island — close enough to the birth of ska and rocksteady to have absorbed it in his bones rather than learned it from records. He moved to the United States in 1961, and the origin story that follows is the kind that sounds invented: Frank Sinatra heard him playing in a Miami club, and Jilly Rizzo, Sinatra's friend and club owner, put him behind the piano at Jilly's in New York. From there Alexander fell in with Milt Jackson and Ray Brown, two of the most demanding rhythm partners in the music, and never really left the top tier.
What makes him singular isn't the bebop fluency, formidable as it is. It's the refusal to file his Jamaican identity under "influence." Where other jazz musicians borrow a Caribbean lilt for a novelty track, Alexander built an entire body of work on the premise that Ellington and Marley belong on the same bandstand. His 1970s and '80s records — and the touring bands he still leads — regularly put a straight-ahead trio next to a melodica, a nyabinghi drum, or Ernest Ranglin's guitar, and treat the collision as normal.
What to listen for
This playlist front-loads the argument. "Love and Happiness" and "Row Fisherman" pair him with Ernest Ranglin, the guitarist who played on the first ska sessions at Studio One and arranged Millie Small's "My Boy Lollipop" — two Jamaican elders talking shop. The Marley material is the emotional center: "No Woman No Cry" live, "Stir It Up," "Jammin'," "Could You Be Loved," "No More Trouble." Alexander has spent decades on this songbook and he treats it as seriously as anyone treats Gershwin, finding the harmonic room in melodies most players would just state and leave alone.
Then there's the other side of the ledger. "Come Fly With Me" is a nod back to the Sinatra connection. "Here Comes the Sun" and "You Make Me Feel Brand New" show the pop instincts. And "Soulful Strut" with Sly & Robbie — the most-recorded rhythm section in reggae history — is the thesis in miniature: a Chicago soul instrumental from 1968, played by a jazz pianist, over a Jamaican riddim section, and somehow it sounds like it was always meant to go that way.
Put it on and let it run. The sequencing rewards patience — the deeper you get, the less the categories matter.
Go deeper
If this opens something up, the album to find is Stir It Up (1999), where Alexander tackles the Marley songbook at length, or Harlem–Kingston Express (2011), a live record that literally splits his band in two — a jazz trio on one side, a reggae section on the other — and moves between them mid-song. It is the clearest recorded statement of the idea this playlist is built on.
From there, chase the sidemen. Ernest Ranglin's Below the Bassline (1996) is the essential document of Jamaica's greatest guitarist in a jazz setting. Sly & Robbie will take you anywhere in reggae you want to go. And if the Sinatra thread interests you, Oscar Peterson is the pianist Alexander is most often compared to — the technique is comparable; the island is not.
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