Thelonious Monk

When I sit at my desk, I can rest my eyes from the screen and look up to my left to see a black and white photograph of the loneliest monk in profile. There are flecks of grey in his goatie and, as was his wont, he's sporting one of his madcap hats: this one, a cross between a kind of Sean O'Casey-style smoking hat and a tea cosy.

I suppose my own weakness for hats is another reason why I've loved Thelonious Monk for so long. Monk's headgear was a truly whacky and eclectic collection, but then he was one of those eccentric, obsessive artists who seem to inhabit a planet apart from mere mortals.

My first close encounter with Monk came as a young adolescent, watching the BBC2 jazz programmes from the Ronnie Scott Club with my father. Neither of us really got him then, but there was something compelling about his music. It wasn't quite avant-garde in the Cecil Taylor sense of the label, but it was definitely... different. Melodies of sorts were always kind of crooked. There was something slightly dissonant and disconcerting, something 'off minor' about his music, to use one of Monk's own playful titles.

Few would argue that Monk is one of the giants of post-war American jazz: up there with Duke Ellington, Charlie Parker, Miles Davis and Charles Mingus. He wrote some of the most elliptical tunes in the modern musical language: hum-along tunes that come back to haunt you. Some of them, like 'Little Rootie Tootie', 'Nutty' and 'Bye-ya' to name but three, could almost be nursery rhymes for Donnie Darko and other unhinged young souls. Others, like 'Ruby My Dear', 'Coming on the Hudson' and 'Round Midnight' are some of the most poignant and atmospheric melodies composed in any genre.

If you don't believe me, you could have asked the remarkable Baroness Panonnica de Koenigswarter before her death in 1988. A member of the clan Rothschild, she married a baronial French diplomat, fought for the Free French against the Nazis, and worked for General de Gaulle before, legend has it, hearing Monk's 'Round Midnight' in New York. So spellbound was she, that she decided to stay in New York, renounce her husband and leave her five children in Europe.

If I could find a producer bold – and mad – enough to pay me to write the script, you could watch the whole weird and wonderful tale unfold in a film about the 'Jazz Baroness', patron saint of New York be-boppers. While her relationship with that nice Mr. Parker ended when Bird died in her suite of rooms in 1955, her relationship with Monk endured 28 years. She even took legal responsibility for him when they were both 'detained' for possession of marijuana. He sure as hell must have had something about him.

Disinherited by her family, the baroness was adored by the jazz fraternity. There are many-a tribute tune written in her honour, such as Horace Silver's 'Nica's Dream', but none as gorgeous as Monk's 'Pannonica'. Probably suffering from manic depression or some such mental illness, the failing composer spent the final six years of his life as his patron's house guest in Weehawken, New Jersey.

Failing by then he certainly was. There are three distinct phases to Monk's career. In the beginning, there was Monk the singular be-bopper, whose two volumes of Genius of Modern Music for Blue Note and early '50s recordings for the Prestige label represent the well-spring for the final phase of his career. With his creative light on the wane, he endlessly re-cycled his best numbers for the Columbia label, mainly in a quartet format. It was a little like Claude Monet's final phase, when he painted water lilies and cathedral facades and haystacks in every different light of day. Once you've seen one haystack, you've seen 'em all. Arguably.

In between came the fruitful second half of the 1950s, recording for the Riverside label earlier songs and new material written during the three years or so when Monk's New York cabaret license was revoked on taking the rap for his friend, Bud Powell, after a marijuana bust. Within that period came the lovely set of songs he recorded with John Coltrane and a fine live solo performance that belies the misconception that Monk couldn't play.

Like Miles Davis, Monk suffered this kind of critical slur throughout his career. Both were essentially minimalists who seemed to believe that less is more. Monk's music is full of pregnant pauses when you can almost hear his thought processes working: wondering which note to play next before coming down forthrightly on his choice. His style was edgy at times, frequently funny and rarely dull.

If Monk was 'difficult', as he has sometimes been branded, the difficulty for me is in picking an individual album to capture his quintessence. The album with John Coltrane is tempting, but the material isn't necessarily his finest. Genius of Modern Music probably ticks the most boxes, but there's no 'Little Rootie Tootie' – and if ever a song could make the most depressed misanthrope beam with joy, it must be that one.

So I come back to the first collection of his I ever bought – at a market stall in Kingston-upon-Thames while visiting my parental grandparents, I believe. I certainly didn't propose playing it to the old folks. Called simply Thelonious Monk, it's one of those French-distributed two-fers that I collected in the late '70s and beyond.

It's a collection of the final flowering of the Monk Mk1 genius: the recordings he made under his own name for the Prestige label during his enforced sabbatical and before he switched to Riverside. There's no 'Round Midnight', but you can find 1,001 versions of it elsewhere (including a sumptuous version arranged for big band by Joe Jackson, no less). But there are all kinds of other reasons to love it.

There are two sides of trio music, arguably the format that suited him best, with versions of 'Rootie Tootie', 'Nutty' and 'Trinkle Trinkle', along with re-imaginings of standards like 'Sweet and Lovely', 'These Foolish Things' and the song that he would come back to over and over, like a dog at a particularly savoury bone, 'Just a Gigolo'.

And there are two sides of music with a quintet – one of which features the inspired combination of Sonny Rollins on tenor sax and Julius Watkins on French horn. It's a weird sonic palette that colours the angular melodies of 'Let's Call This', 'Think Of One' and 'Friday the 13^th' with a sense of mystery.

His playing is every bit as inspired throughout as his compositions. At times, you hear vestiges of the old stride tradition that he inherited from Fats Waller and James P. Johnson. More often, though, you hear the restless experimenter whose sound – as one commentator perceptibly observed – is 'the sound of a composer thinking out loud at the piano'. The result is music that is rhythmic, angular, daring, unsettling and humorous. Like his hats, it never fails to surprise and delight me.