Best 1950s Jazz Songs

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1. 1
   CB
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   Almost Blue

   Chet Baker · from Chet Baker Sings (1954)

   The trumpet solo so good Elvis Costello named an album after it.

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2. 2
   SR
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   St. Thomas

   Sonny Rollins · from Saxophone Colossus (1956)

   Calypso and bebop in three minutes of pure pleasure.

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3. 3
   TM
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   Round Midnight

   Thelonious Monk · from Brilliant Corners (1957)

   The most covered jazz ballad after the Great American Songbook.

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4. 4
   CA
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   Autumn Leaves

   Cannonball Adderley · from Somethin' Else (1958)

   A blue, late-night reading with Miles Davis.

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5. 5
   BE
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   Peace Piece

   Bill Evans · from Everybody Digs Bill Evans (1958)

   Ten minutes of one chord, pedal tone, and complete transcendence.

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6. 6
   MD
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   So What

   Miles Davis · from Kind of Blue (1959)

   The modal opening that launched a thousand players.

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7. 7
   DB
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   Take Five

   Dave Brubeck · from Time Out (1959)

   The 5/4 signature no one expected jazz to accept.

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8. 8
   CM
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   Goodbye Pork Pie Hat

   Charles Mingus · from Mingus Ah Um (1959)

   The Lester Young elegy that became Mingus's most enduring piece.

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9. 9
   MD
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   Freddie Freeloader

   Miles Davis · from Kind of Blue (1959)

   The blues, finally, after four modal explorations — Wynton Kelly's piano debut.

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10. 10
    OC
    ▶

    Lonely Woman

    Ornette Coleman · from The Shape of Jazz to Come (1959)

    Don Cherry's trumpet and Coleman's alto — the most beautiful piece of free jazz.

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