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Have Yourself a Merry Heap of Christmas Jazz, Handpicked by Our Announcers, in Take Five

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Natalie Cole performs at a Rockefeller Center Tree Lighting ceremony in 2000.

This week, WBGO announcers take over Take Five with 12 — wait, make that a baker’s dozen — favorite holiday tracks. 

Natalie Cole, “Merry Christmas Baby”

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Holly & Ivy, Natalie Cole’s Christmas album, is wonderful in its breadth, ranging from big band jazz to gospel-influenced arrangements and sentimental songs with strings. There are the classic Christmas songs, like “Merry Christmas Baby,” and songs I've never heard before but dig, like “The Little Boy That Santa Claus Forgot.” — Rob Crocker, Saturday Evening Jazz and Sunday Afternoon Jazz

Duke Pearson, “Sleigh Ride”

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Pianist Duke Pearson was a major part of Blue Note recordings by Stanley Turrentine, Donald Byrd and Lee Morgan, in addition to his own small-group and big band sessions for the label. Blue Note chose to open their Ultimate Jazz Christmas collection with a swingin’ version of “Sleigh Ride,” with Pearson on celeste and piano, alongside bassist Bob Cranshaw, drummer Mickey Roker and percussionist Airto Moreira. — Gary Walker, Morning Jazz

Charles Brown, “Merry Christmas Baby”

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Growing up it wasn't Christmas in my house until my dad played this song. The moment Charles Brown’s soulful lilting vocals sing “Merry Christmas Baby, sure do treat me nice,” I am instantly transported back to being a little kid in Brooklyn. With that opening line, you instantly understand why they called Charles the Honey Dripper. I can almost hear my dad singing along. — Monifa Brown, Saturday Afternoon Jazz [Ed Note: Cool Christmas Blues has just been reissued on vinyl by Craft Recordings.]

Irma Thomas, “O Holy Night”

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“O Holy Night” has always been my one of my favorite Christmas hymns. New Orleans singer Irma Thomas’ version with a gospel choir always lifts the spirits of everyone in the room when I play it at home. — Felix Hernandez, Rhythm Revue

Hank Crawford, “O Holy Night”

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I had a scheduled recording session with Hank Crawford when Milestone called requesting a tune for inclusion on a Christmas anthology. Hank came up with a wonderful arrangement of “O Holy Night” which incorporated a portion of “We Will Overcome.” It is my all-time favorite. — Bob Porter, Portraits in Blue, Saturday Morning Function and WBGO Swing Party

Eartha Kitt, “Santa Baby”

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“Santa Baby” was a big hit for Eartha Kitt in the mid ‘50s. I don't know if she ever got to possess all of the things on her Christmas list, but one thing is for sure: she owned that song. Even though many others have recorded it, hers remains the definitive version. As Eartha said, ‘’I am the original Material Girl.” — Rhonda Hamilton, Mid-Day Jazz

Nat King Cole, “The Christmas Song”

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The nostalgia that Nat King Cole’s “The Christmas Song” brings is instant. The innocence of a kid who believes in Santa Claus overcomes me, and I remember why this holiday is so special to so many. — Nicole Sweeney, Evening Jazz

Miles Davis Featuring Bob Dorough, “Blue Xmas (To Whom It May Concern)”

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Best as I remember, Bob Dorough said he’d been playing some gigs, opening for Bird. He got to know Miles, and he gets a call, and that voice rasps “Write me a Christmas song!” (They also recorded “Nothing Like You,” which ended up on Sorcerer.) — Michael Bourne, Singers Unlimited and Blues Break

Donny Hathaway, “This Christmas”

The intro to this song — dadada da-da, da da-da-dadada — along with those jingling bells, signals it's time to decorate the tree, the house, “turn on” the fireplace, eat fruitcake and drink eggnog with family and friends! — Lezlie Harrison

Wynton Marsalis, “Silent Night” (Featuring Kathleen Battle)

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There are quite a few jazz versions of seasonal songs that move me, but none quite so much as this version of “Silent Night.” Wynton Marsalis took a favorite Austrian carol and turned it into an authentic New Orleans blues, with the bonus of Kathleen Battle’s gorgeous soprano — marvelous! — Brian Delp, Jazz After Hours

Dexter Gordon, “Have Yourself a Merry Little Christmas”

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Beginning with a simple piano and cymbal introduction, Dexter then enters with a sound so confident, so comforting, so... welcoming, as though he has invited us into his home to decorate his tree, to enjoy some eggnog, to mingle and engage with friends and loved ones. — Dan Karcher

Jimmy Smith, “Greensleeves”

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Jimmy Smith's rendition of “Greensleeves,” from Christmas Cookin', is one of the hippest holiday songs that I can hear all year long. He’s joined by Kenny Burrell (guitar) and Grady Tate (drums), and no matter my mood, they swing me into a festive frame of mind. — Sheila Anderson, Weekend Jazz After Hours, Salon Sessions, Sunday Night Music Mix

Kirk Whalum, “The Little (Ghetto) Drummer Boy”

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I never liked “The Little Drummer Boy” — that is, until Kirk Whalum did the “The Little (Ghetto) Drummer Boy” on his 2001 CD The Christmas Message.  Finally, a drummer boy with a compelling beat, one that even Baby Jesus liked! — Bill Daughtry, Friday Afternoon Jazz