The playlist: Christmas jazz – Billie Holiday, Chet Baker, Miles Davis and more

A festive 10-song special, from White Christmas and an all-star version of Winter Wonderland to a capricious take on Santa Claus Is Coming to Town

Billie Holiday – I’ve Got My Love to Keep Me Warm

Billie Holiday, who died in 1959 at the age of 44, transformed the pop singing of her era and beyond. (Frank Sinatra regarded her to be his biggest influence). But she ended up broke, scared and handcuffed to her final hospital bed by the narcotics squad. That sad ending doesn’t dim the magic of Holiday’s music. This Christmas song, first recorded by her in 1937, is an object lesson in subtle timing, driven by Lady Day’s signature mix of realism and hope.

John Zorn – Santa Claus is Coming to Town

Free-jazz sax screamer, postmodernist game-theory composer, wild-man deconstructionist of Ennio Morricone and Ornette Coleman: could New York iconoclast John Zorn ever get cosy about Christmas? He showed that was possible – and reminded fans of his fiercest music that he has always made room, albeit idiosyncratically, for traditional songs with rich cultural histories – on his album A Dreamer’s Christmas in 2011. The conjunction of Marc Ribot’s Derek Bailey-esque guitar chords and Jamie Saft’s silky piano seems to perfectly catch a Yuletide chemistry of tension and blandness.

Carla Bley – O Tannenbaum

The great contemporary jazz composer Carla Bley has the right backstory to interpret Christmas music with affection, solemnity, subversion and wit. The daughter of a California choirmaster, she was a church pianist as a child, then ran away to become a teenage ice-skater, a waitress in New York jazz clubs and by the 1960s one of the most distinctive and idiomatically open inheritors of the big-ensemble jazz traditions of Duke Ellington and Gil Evans. Bley, who is a superb writer for horn sections, arranged Christmas classics including Silent Night, Jingle Bells, God Rest Ye Merry Gentlemen and O Tannenbaum, for a Berlin concert in 2008. Her husband Steve Swallow was on bass and they were joined by the Partyka Brass Quintet, with German trumpet star Axel Schlosser.

Bill Evans – Santa Claus Is Coming to Town

Few jazz pianists brought more diverse resources to the reinvention of familiar music than the late Bill Evans, whose improvisation balanced the graceful and the unexpected. Evans recorded Santa Claus Is Coming to Town with his Trio 64, alongside bassist Gary Peacock and drummer Paul Motian – but this quietly capricious solo version is an even better representation of the contrast between this breezy Christmas plaything and the blues.

Charlie Parker – White Christmas

Saxophonist and pioneering bebop genius Charlie Parker may have spent a good deal of his short adult life not knowing or much caring what day it was, but he was in the right place at the right time for this recording of White Christmas, on Christmas Day 1948. Parker’s band was packed with first-generation beboppers, with Kenny Dorham on trumpet, Al Haig on piano, Tommy Potter on bass and Max Roach on drums.

Chet Baker and Lighthouse All-Stars – Winter Wonderland

Another jazz celebrity with a sometimes approximate sense of time and place was Chet Baker, the white west coast poster boy who even Charlie Parker admired. Baker was a key figure in the California “cool school” of beboppers, who usually performed this nervy music in a less frenetic manner than New Yorkers. But there’s nothing laid-back about this 1953 version of Winter Wonderland, played by Baker and the house-band at LA’s beachside Lighthouse Cafe. Roach is also at the drumkit on this one, with Lighthouse All-Stars’ Russ Freeman on piano and club manager Howard Rumsey on bass.

Miles Davis ft Bob Dorough – Blue Xmas (To Whom It May Concern)

Miles Davis’s music was on a cusp in 1962. Having recorded one of the most influential of all jazz adventures with the spacious Kind of Blue in 1959, he was in search of new pastures and a new band. The 1962 studio band that made this quirky beat poet’s Christmas original included the Kind of Blue rhythm team of bassist Paul Chambers and drummer Jimmy Cobb, but also the pithy sax sound of newcomer Wayne Shorter. When Columbia Records requested a Christmas song, Davis characteristically turned to a performer who wouldn’t deliver one straight. He enlisted Bob Dorough, a bebop-influenced singer-songwriter whose improvisations on Charlie Parker solos had already caught Davis’s ear.

Django Reinhardt and Michel Warlop – Christmas Swing

If Davis’s reaction to Christmas music was to find a cool way of turning it on its head, the instincts of Django Reinhardt were to get as much unselfconscious fun out of playing it as he could. Reinhardt’s most famous and compatible violin partner was Stéphane Grappelli, but this 1937 track is dominated by the fire of Michel Warlop, a brilliant but short-lived prodigy who had switched from a promising classical career to jazz in his 20s.

Henry Kaiser – Christmas on Bear Mountain

Bay Area guitarist Henry Kaiser grabbed the caustic inspirations of British improv guitar guru Derek Bailey in the 1970s and ran with them through warped blues, world music, Sun Ra, avant-fusion and a lot more. Not much more than the title of this track from 1980s Aloha album has a seasonal hook perhaps, but some might detect a jangle of sleigh bells in there somewhere.

Tom Harrell – The Christmas Song

Like Bley or the late Kenny Wheeler, the American trumpeter and composer Tom Harrell who can shift the implications of a piece of music with the most subversively gentle harmonic tweaks – and he writes music that sounds familiar while eschewing cliche. Here’s a typically shapely piece of Harrell Christmas music, with a superb band featuring Joe Lovano on sax, Wayne Shorter pianist Danilo Pérez, and the rhythm section dream team bassist Charlie Haden and drummer Paul Motian.

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