In 1966, Columbia Records released a Miles Davis album called “Miles Smiles,” the cover of which showed the legendary trumpeter curling his lips ever so slightly upward. Davis had long since built up a reputation as the least smiling man in jazz, and Columbia underscored that image with this album cover: This was the closest thing to a smile Miles was willing to flash.

Davis was the first jazz musician to make seriousness part of his shtick. Whereas his most important predecessors – Louis Armstrong, Roy Eldridge and Dizzy Gillespie – were natural showmen, Davis pioneered his own brand of anti-showmanship. Coolness and nonchalance were key.

There was a lighter side of Miles, though, and it comes through on a new four-CD box, “The Legendary Prestige Quintet Sessions.” The music on this set, which was recorded between 1955 and 1958 and released last week by Fantasy Records to commemorate the 80th anniversary of Davis’s birth, is some of the most enjoyable of his long, eventful career. The package includes a previously unissued nightclub set from 1958 in which Miles, playing alongside John Coltrane in their groundbreaking quintet, sounds like he can’t stop smiling.

Davis’s buoyant mood is clear in “Bye, Bye Blackbird,” a somewhat frivolous jazz standard from 1926 that Davis had transformed into one of his signature anthems. Many jazzmen of Davis’s generation liked to throw in random quotations from familiar songs – Dexter Gordon was a master of this, as was Miles’s mentor, Charlie Parker – but this was something Davis almost never did. (I’ve always suspected he thought it was too silly or otherwise beneath him.)

Here on “Blackbird,” however, he throws in a phrase that could have been inspired by “I Wish I Were in Love Again,” and another sounds like “Rockin’ in Rhythm.” Later, he dwells on Leonard Bernstein’s “Maria,” a song from “West Side Story,” which opened in 1957. Bernstein’s hybrid of popular and high art was the talk of New York intelligentsia, and Davis’s reference to “Maria” might offer a clue that the trumpeter wanted to attain a similar kind of crossover success.

The Prestige sessions were recorded during the years (1955-58) when Davis was reinventing himself, if not yet as the prince of darkness, then certainly as a purveyor of high art rather than lowbrow entertainment. He wanted his music to be seen as something akin to chamber music, rather than a background for dancing or making out. Davis had already led multiple lives in the jazz world – as a Parker disciple (1946-48), as the leader of the “Birth of the Cool” band (1949-50), as a participant in occasionally brilliant sessions for Prestige and Blue Note in the early 1950s. By 1955, he had put his drug problems behind him (at least temporarily) and signed with Columbia Records following a spectacular appearance at the Newport Jazz Festival. Under the guidance of Columbia producer George Avakian, Davis entered the studio with Coltrane and the stellar rhythm section of pianist Red Garland, bassist Paul Chambers, and drummer Philly Joe Jones.

Davis was still under contract to Prestige, however, and he was obligated to cut several more albums for the smaller company. For 18 months or so the quintet recorded for both labels.Whereas the Columbia albums – “‘Round About Midnight” and “Circle in the ‘Round” – were meticulously produced, Miles and his men simply banged out the songs on of their Prestige dates.They did only one take for each of 32 different tunes (including “Diane,” on which Coltrane let out a killer squeak), for a total three hours and 13 minutes of music.

At the time, Prestige released the music on five LPs: “The New Miles Davis Quintet,” “Workin’ With the Miles Davis Quintet,” and then “Relaxin’…,” “Steamin’…,” and “Cookin’ With the Miles Davis Quintet.” The content of the original albums was determined seemingly at random, and Davis apparently played no part in how they were sequenced or what tune went where. Still, some of Davis’s best material is here: treatments of early Parker-Gillespie works, like “Salt Peanuts” and “Woody n’ You”; beautiful ballads like “When I Fall in Love” and “Something I Dreamed Last Night”; and reprises of swinging standards by Duke Ellington (“Just Squeeze Me”) and Benny Carter (“When Lights Are Low”).

But the highlights are the more whimsical moments. Included here is Davis’s treatment of Dave Brubeck’s cute and capricious “In Your Own Sweet Way,” which probably did more to make it into a jazz standard than its composer did. On a version of the primal blues “Walkin’,” recorded at the Blue Note Philadelphia in 1956, Davis launches into a solo that is much more loosey-goosey than we expect an improvisation by Davis on the blues to be. And he seems to revel in goofy songs from the 1920s like “S’posin'” and “Dianne.” The latter is particularly interesting: Far from sounding like “serious” jazz, this 1927 tune in 3/4 time sounds like a real old-fashioned waltz, sweet and danceable.

Also among the 39 minutes of previously unheard live material are two tunes recorded on the original “Tonight Show” from 1956. This soundtrack includes a moment where Davis speaks briefly as host Steve Allen tries, humorously, to explain his music to Middle America. It’s one of the earliest recordings of Davis’s voice, which had already been ruined by a recent throat operation. The way he spoke, in a grumbling whisper, somehow complimented his music and foreshadowed his transformation into “The Dark Magus.”

The set closes with an interesting postscript: Davis’s Quintet performing at New York’s Cafe Bohemia in May 1958, by which time Garland had been replaced by Bill Evans. Although four of the musicians are the same and most of the tunes are familiar, this group sounds a lot more like the one that would soon record the classic “Kind of Blue.”

wfriedwald@nysun.com