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- – After Midnight (1956). Surviving racist attacks and skepticism toward his crossover success in a “white” music industry, Cole became legendary as both a jazz pianist and popular singer. This definitive LP revives earlier hits like “Sweet Lorraine” and “Route 66” with the Cole Trio augmented by horns and Stuff Smith’s Grappelli-like violin. Ballads like “Lonely One” and “Blame It on My Youth” melt against Cole’s intimate, ever-soulful singing.

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- – Black Coffee (1953/56). Originally eight songs on vinyl 10-inch, Black Coffee featured Lee at her sultry best – epitomizing the emboldened, urbane feminine persona of the pre-rock era. Later sessions from 1956 added more pizazz, with echoes of bop and cool jazz on Lee’s renditions of “Gee Baby, Ain’t I Good to You” and a smoldering “You’re My Thrill.” Lee’s influence continues to resonate in the vocal styles of Joni Mitchell and Billie Eilish.

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- - Lady Sings the Blues (1956). Despite the ravages affecting her health, Holiday tapped a late-career wellspring on sets like Velvet Mood and this LP -- both from '56. Holiday revisits hits like "Strange Fruit" and "God Bless the Child" along with newer material such as the title track. A sextet or septet provides restrained musical settings for Holiday's matter-of-fact delivery -- an artist who knows the end is nigh but chooses to forge on.

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/ – Jazz at Massey Hall (1953). This live one-off, captured by Charles Mingus on a portable tape deck, featured Parker in the company of Dizzy Gillespie, Bud Powell, Max Roach, and Mingus (on bass) at Toronto’s Massey Hall. A spirited “Perdido” leads the set, followed by Dizzy’s infectious “Salt Peanuts” and a set of standards ending with a definitive “A Night in Tunisia.” Low audio fidelity aside, this is as good as bebop gets.

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- – The Shape of Jazz to Come (1959). From the plastic saxophone Coleman cradles on the cover to the near-abandonment of traditional harmony to the free-form soloing by the musicians, everything about this LP felt new and slightly dangerous in 1959. Although “Lonely Woman,” “Eventually,” “Peace,” etc. aren’t exactly “free jazz” as it would be understood in the 60s, the radical shift in form divided the naysayers from the believers.

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- – The Great Artistry of… (1953). Django was to jazz guitar what Hendrix was to rock – creating new voicings with dazzling technique. This LP, made months Django’s death at age 43, finds the Belgian-Romani virtuoso playing electric guitar with bebop backing. His own “Nuages” precedes tunes by Porter/ Weill and a blazing take on Barroso’s “Brazil.” Amplifier breakup gives Django’s trademark runs a touch of grit on this jazz guitar manifesto.

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- and the Jazz Messengers (1959). AKA: Moanin’, this LP combines elements of blues, gospel, and Dixie march in a hard bop framework, highlighted by pianist Bobby Timmons’ infectious title track and drummer Blakey’s percussive mayhem on “The Drum Thunder Suite.” Trumpeter Lee Morgan adds his typical scene-chewing solos on “Are You Real” and “Come Rain or Come Shine,” and tenor man Benny Golson evokes big-band fanfares over a soulful groove.

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- – Blue Train (1958). Although Trane would only peak a couple of years later, on Giant Steps, this LP was a glorious leadup. “Moment’s Notice” and “Lazy Bird” are early evidence of Trane’s “sheets of sound” (Ira Gitler’s phrase), and the title track is a strutting blues soon to inform Trane’s work on Davis’s Kind of Blue. Good as Coltrane himself is, Lee Morgan – age 19 – steals the spotlight whenever his dazzling trumpet lights up a tune.

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- – Brilliant Corners (1957). After years of neglect by the jazz scene and gigs in empty rooms, Monk triumphed on this challenging set with Sonny Rollins on tenor sax, Max Roach on drums, and other top sidemen. The angular, tempo-shifting title track stumped the band, until producer Orrin Keepnews spliced together a useable take. Quieter moments including the celeste-embellished “Pannonica” and Monk’s emotive solo piano on “I Surrender, Dear.”

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- – Pithecanthropus Erectus (1956). Mingus used the metaphor of fossilized Java Man (Pithcanthropus erectus) for a tone poem about the rise and eventual fall of humankind. Saxophonists J.R. Monterose and Jackie McLean (who had a famous punch-up with the wily leader) help to evoke musical film noir on “Foggy Day,” before the quieter “Profile of Jackie” and bop-heavy “Love Chant.” A musical defiance of boundaries – and a sign of things to come.

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- – Django (1956). Playing cool and composed when most jazzers were bopping hard, the MJQ brought third-stream classical elements to modern jazz – managing to sound bluesy at the same time (at the insistence of soon-to-depart drummer Kenny Clarke). Milt Jackson’s vibraphone is an acquired taste for those used to horns, but his work complements John Lewis’s lovely elegy for Django Reinhardt and pieces inspired by former boss Dizzy Gillespie.

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- – Saxophone Colossus (1957). Tireless craftsman of the tenor sax, Sonny made his mark with this set of calypso, hard bop and blues pieces unified by the master’s precise soloing and sublime use of space. “St. Thomas” gets Caribbean funky, before “You Don’t Know What Love Is” waxes romantic and Weill’s “Moritat” gets Mack’s knife a-swinging. But the finest moment is “Blue 7,” a stately blues exploration of which even Muddy Waters would be proud.

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- – Milestones (1958). The fiery precursor to the more subdued Kind of Blue, Milestones features the Davis sestet – Coltrane back after a break, plus Cannonball Adderley on alto sax – playing a mix of hard bop (“Dr. Jekyll” and “Two Bass Hit,” two of Davis’s hottest numbers of the period) and lyrical excursions – including the extended “Sid’s Ahead.” Modal jazz informs the title track, setting the stage for Blue’s deeper dive the following year.

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- – Subconscious-Lee (1955). These 1949-50 sessions were a key document in the so-called Tristano school – students of pianist/ teacher Lennie Tristano who carved their own niche in 40s-50s bop. Konitz, whose alto sax also graced Miles’s Birth of the Cool, plays with clean melodicism against Tristano’s cool chords and Billy Bauer’s lean guitar. The solos, including Warne Marsh’s tenor sax on some tracks, are like fluid conversations among friends.

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- – Somethin’ Else (1958). Adderley’s only Blue Note LP paired the alto saxophonist with Miles Davis and a crack rhythm section, including drummer Art Blakey. Miles solos first on “Autumn Leaves” and “Love for Sale,” his sparse lyricism leaving room for Adderley’s blues-and-Bird-influenced virtuosity. Brother Nat’s “One for Daddy-O” is another blues form on the disc that prologued Miles and Cannonball’s work on Milestones and Kind of Blue.

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- – Chet Baker Sings (1954/56). After earning respect for his trumpet accompaniment of Bird and Gerry Mulligan, Baker teased the popular conscience with his technically limited but emotionally affecting singing on pieces like “My Funny Valentine” and “I Fall in Love Too Easily.” An emblem of fifties cool, Baker’s jazz chops remain strong on the melodic trumpet solos that provide a self-referential call-and-response in his forlorn romanticism.
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- – Quartet Volume 1 (1952). The LA-based Mulligan Quartet helped inspire “cool” jazz with its distinctive pairing of Mulligan’s deep baritone sax with Chet Baker’s nimble trumpet. With Chico Hamilton on drums and different bassists, the pianoless quartet – sparse and raw without conventional harmonic accompaniment – stood out on tracks like Baker’s bustling “Freeway” and the Latin-flared “Frenesi.” Streaming expands on the original 10-inch LP.

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- – Plays W.C. Handy (1954). Armstrong sounds revivified and full of joy interpreting Handy’s seminal blues compositions – “St. Louis Blues,” “Memphis Blues,” “Yellow Dog Rag,” etc. Members of Pops’ small fifties combo – trombonist Trummy Young, clarinetist Barney Bigard, etc. – keep the soloing hot. Vocal trade-offs between Pops’ sandpaper voice and Velma Middleton’s smoother pipes enhance the jamboree feel of this classic set. , ,

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- Lester Young with the Trio (1952/54). Released in 2 volumes and later under other titles, these sessions from late '52 followed Pres's most renowned period of the 40s -- his tenor sax soloing diminished by alcoholism but still vibrant. Peterson, earlier in his career, almost upstages Young with dazzling piano chops on "Tea for Two," "Stardust" et Al. Young's vocal ad lib at the end is a raw treat from the man who coined "cool."

 

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– TOP 20 - - (1996). Although jazz critics prefer Sanders’s Coltrane-oriented Crescent with Love (1993), MFH was a fascinating hybrid of modern jazz, African worldbeat and R&B. Sanders’ virtuosic sax is just one element among funky bass and drums, chanted vocals (“Our Roots Began in Africa” – surely one of the era’s great earworms), and the kora (on the lovely “Kumba”). A crossover gem for jazzers and non-jazzers alike.
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