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Workin' (or Cookin')
Miles Davis Quintet
1956 [Prestige]

In marathon 1956 recording sessions Davis’ first classic quintet featuring John Coltrane drew on its live repertoire to put down the material that would appear on the contractual obligation albums Relaxin', Cookin’, Workin' & Steamin’. They are all terrific, with Workin' getting the nod over the others for its significant original content.

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'Round About Midnight
Miles Davis
1956 [Columbia]

Recorded over roughly the same period as the four album marathon session that saw him fulfil his obligations to Prestige, Davis' first major-label recording found his quintet laying the groundwork for the classic Kind of Blue album. Tenor John Coltrane hits just the right notes in this fine record that oozes style and sophistication.

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Porgy and Bess
Miles Davis
1959 [Columbia]

Miles Davis and arranger/pianist Gil Evans had previously worked together on the Birth of the Cool recordings. This was the second of three albums they made together with Columbia. It is a stunning and sublime interpretation of George Gershwin's music, and shows the intricate and intimate musical relationship the two enjoyed together.

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Milestones
Miles Davis
1958 [Columbia]

Featuring the same personnel that appeared on the follow-up Kind of Blue, this record more than holds its own as one of the true classics of jazz. With Coltrane, Cannonball Adderley and Red Garland's trio on board it was hard to miss. In a quirk of history, however, its justly famous successor was so good that Milestones was almost forgotten.

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Kind of Blue
Miles Davis
1959 [Columbia]

Regarded as a landmark record in Davis' conceptual development of modal jazz. The songs are built on chords & scales rather than the key in which they are played. The result is a moving record of haunting beauty - played to perfection by Davis, John Coltrane, Cannonball Adderley, Bill Evans, Wynton Kelly, Paul Chambers and Jimmy Cobb.

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Sketches of Spain
Miles Davis
1960 [Columbia]

Arguably the best of the late-50s Miles Davis collaborations with composer/arranger Gil Evans, although there is nothing wrong with the others. Anchoring the record is the stirring 'Concierto de Aranjuez' - a Spanish classical piece around which the rest of the album is built. The orchestra features a host of top-flight trumpeters. Brilliant.

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Miles Smiles
Miles Davis Quintet
1966 [Columbia]

A transitional album for Davis chronologically sandwiched between the Gil Evans collaborations and his fusion period. Smiles is widely regarded as the best album by Davis' second quintet featuring pianist Herbie Hancock and tenor Wayne Shorter. While there are no real surprises here, the record certainly maintains Davis' stellar standards.

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Nefertiti
Miles Davis
1967 [Columbia]

A widely debated record in terms of its historical significance, Nefertiti showcases Davis’ second classic quintet at their exploratory best. While there are certainly freeform elements, most of the music is still recognisable as hard bop. Wayne Shorter and Herbie Hancock are superb, with plenty of pointers to fusion and the future on hand.