Vinyl Reports

At first glance, Miles 55: The Prestige Recordings, a new deluxe 180g 3LP box set that’s being released today, August 22, 2025, and celebrates seminal mid-1950s music by Miles Davis and some of his most important bands of the era (featuring future legends like John Coltrane, Jackie McClean, Red Garland, and Milt Jackson) may appear to be somewhat redundant to hyper-aware jazz collectors. But for a new generation that has not yet gotten into Davis’ catalog beyond his landmark August 1959 modal masterpiece LP Kind of Blue and the jazz-rock fusion breakthrough of March 1970’s 2LP set Bitches Brew (both from his quite fertile Columbia period), this newly mastered 3LP collection from Craft Recordings just may be the perfect stepping-stone release to get them over the hump — not to mention having great appeal to Miles completists and fellow audiophiles alike.

I know that whenever I have approached what I call “going deep” into a legacy artist’s back catalog, it can be somewhat daunting trying to figure out where to start. Like Charles Mingus, John Coltrane, Duke Ellington, and Louis Armstrong, Miles Davis was super-prolific, releasing dozens, if not hundreds, of recordings during his lifetime — and many more of them continue to appear anew, following his passing in 1991. Heck, I’ve been collecting Miles albums for years, and I am still not close to having them all yet — including an original of one found in this set! (More on that distinction in a bit.)

Still, when I first read about Miles 55: The Prestige Recordings, I had to do a bit of a double take, putting the press release on pause for a moment to check if I was understanding what I was reading in it correctly. You see, the three albums that this collection is curated from have been reissued over the years. In fact, two of them were recently released individually in late 2024 and early 2025 by Craft in beautiful recreations of the rare original packaging, including Prestige’s iconic “fireworks” label, and both sporting fresh vinyl lacquers cut from the master tapes by Kevin Gray. Those individual titles are Miles: The New Miles Davis Quintet (August 2024; CR00722) and The Musings of Miles (April 2025; CR00854). The third LP in this box, Miles Davis and Milt Jackson: Quintet / Sextet, was reissued by Concord (owners of Craft, and the Prestige catalog) around 2015 (OJC-012 / P-7034), as far as I can tell from online sources. The point is, it’s not like the music in Miles 55 is unavailable on vinyl these days for those who might be interested. It is there for the taking — but it will cost you.

This conundrum of course raises the marketing-related question: How do you trigger consumer interest in shelling out for this earlier-era Miles Davis music? I know from my crate-digging experiences that there are many younger collectors who only associate “good” Miles as the music made during his above-noted, prolific Columbia-era run. Many simply stop with Kind of Blue and Bitches Brew, not knowing where to go next. Thus, repackaging earlier Miles recordings in a thoughtful manner, focusing mostly on the music itself, is a compelling strategy — and releasing a well-annotated, great-sounding retrospective collection like Miles 55 makes some good sense here in 2025, for emerging fans, fellow audiophiles, and Miles aficionados inclusive.

Before we dig down further into the music itself, let’s explore the underlying DNA beneath Miles 55: The Prestige Recordings. From the official press materials, we learn that “all audio has been remastered from the original analog tapes by Grammy-winning engineer Paul Blakemore, with lacquers cut for the vinyl version by Kevin Gray at Cohearent Audio, while physical editions of the collection offer a new essay by Grammy-winning music historian Ashley Kahn (author of Kind of Blue: The Making of the Miles Davis Masterpiece), as well as insightful session notes by Grammy-winning writer, Dan Morgenstern.” We have since further confirmed directly from Craft that the albums in this collection were remastered by Paul Blakemore in hi-res digital, which is what Gray used for cutting these lacquers.

The packaging for Miles 55: The Prestige Recordings is quite lovely, featuring a striking black-and-white hardshell compact box design. The arresting die-cut “55” on the front reveals a colorful mid-century-modern pattern that serves as the cover of the bonus booklet nestled inside, something that carries over into the album covers. The three LPs therein each have their own individual oaktag cardboard sleeves, and the discs within them all have modern custom labels (as opposed to vintage Prestige labels). Each album is housed in a dark black, plastic-lined audiophile-grade inner sleeve. The LPs were manufactured in Germany, at Optimal.

I have no complaints with any of the discs in my copy of this box set. Each 180g LP is pressed on thick, dark black vinyl that is dead-quiet on playback, so the music just emerges without any sense of underlying surface noise. The LPs are all happily well-centered as well. Thus, things are all good on the quality controls front! (Footnote 1)

The SRP for the Miles 55: The Prestige Recordings box set is $109.99, and it is available from Music Direct here, and/or via the MD link graphic ahead of the tracklisting section below. (I’ll also share my thoughts about the relative value propositions as it relates to this box set vs. the individual LPs at the end of my review.)

Before we get into the disc-by-disc overview, some further perspectives from that aforementioned press release might offer helpful insights into the behind-the-scenes which went in the making of this series of recordings. “There was a particular sound that had defined the ’50s,” writes Ashley Kahn in his portion of the Miles 55 liner notes. “It was an approach that balanced a modern, post-bop feel with echoes of a simpler time. And it belonged to one trumpet player in particular. That musician was none other than Miles Davis (1926–1991). By the middle of the decade, Davis was confidently finding himself as a musician, composer, and bandleader. He had certainly paid his dues. After cutting his chops with such luminaries as Charlie Parker, Dizzy Gillespie, and Coleman Hawkins, Davis broke out on his own, first forming a nonet (early recordings of which were eventually released as [1957’s] Birth of the Cool), and scoring a recording contract with Prestige Records. Despite his struggles with substance abuse in the first half of the decade, Davis was clean, focused, and ready to get back to work by 1954.”

The recordings in Miles 55 showcase the emergence of that soon-to-be classic, laid back, Harmon-muted-sound of Davis’ trumpet. The press release goes on to explain: “In between these key moments, Davis was also spending time in the studio, recording marathon sessions that would yield some of his best albums of the decade. Miles 55 comprises three of these dates (all captured by the great Rudy Van Gelder), beginning with June 7th. Davis was still in the early days of solidifying his new band, and this date (a quartet setting) features two musicians that would become permanent members: Philly Joe Jones and Red Garland, with the addition of bassist Oscar Pettiford.”

Moving onward, let’s now explore each LP, disc-by-disc, in the Miles 55: The Prestige Recordings box set. As was done with the prior (and also excellent) Miles 54: The Prestige Recordings 180g 4LP box set, which was released by Craft in November 2024, we have also confirmed with the Craft team that the tracks here on Miles 55 are, quote, “presented in chronological order to showcase the artist’s evolution.”

Thus, on LP1, all the tunes found on the September 1955 release The Musings of Miles (recorded June 7, 1955) are presented in a different running order. LP3 also bears a different tracklisting for the November 16, 1955, recordings that were issued in April 1956 under the title Miles: The New Miles Davis Quintet.

Curiously, LP2 features the music from the August 1956 release (recorded August 5, 1955) Miles Davis and Milt Jackson: Quintet / Sextet presented in the same running order as the original LP. For me personally, this is perhaps the most interesting release in the set, as it is the one that I didn’t yet have in my collection — which also reminds me that I need to track down a copy of the original sometime soon!

As noted earlier, we have confirmed that the three albums in Miles 55: The Prestige Recordings were remastered and cleaned up in hi-res digital platforms. The collective AP braintrust doesn’t have any problem with that, given the resultant sound quality is excellent, especially for monaural recordings of this vintage. In fact, some of these tracks sound downright amazing, especially when you stop to consider their age!

Not surprisingly, Miles 55: The Prestige Recordings does sound a little different compared to the original individual releases, with a subtle increase in brightness and the middle-low end resulting in an ultimately warmer listening experience. The recordings sound less boxy than the individual OJC reissues from 2024 and 2025. (More on those two LPs shortly.) They were not formal remasters, in which the recording might have been re-equalized and/or had other “clean-up” work employed to remove anomalies such as analog tape drop outs and hiss. For example, I noticed that a minor dropout is not apparent on the Miles 55 version of “Just Squeeze Me” (Side 1, Track 1 on the original LP; and LP3, Side E, Track 3 in this new Miles 55 edition).

Not surprisingly, I especially enjoyed the Miles Davis and Milt Jackson: Quintet / Sextet LP (a.k.a. LP2 in the new box set), as I was basically hearing this music for the first time. This is an interesting session, as it features two tunes written by another then up-and-coming player, saxophonist Jackie McClean, as well as future upstart-to-be, pianist Ray Bryant. I am especially digging LP2, Side D, which features McClean’s swinging “Minor March” (Track 1) and Bryant’s wonderful “Changes” (Track 2).

When it comes down to the value propositions I mentioned earlier, the Miles 55: The Prestige Recordings 3LP box set may very well be somewhat slightly more affordable than if you were to buy all three albums individually at their respective list prices. The Musings of Miles and Miles: The New Miles Davis Quintet were, as briefly noted, reissued as part of Craft’s exemplary reboot of the Original Jazz Classic (OJC) series, with each of those two LPs going for $38.99 apiece. Meanwhile, the Concord-issued Miles Davis and Milt Jackson: Quintet / Sextet LP is available for $25.99, but do take note that that edition appears to be an earlier 2015 reissue, put out before the Craft OJC series reboot. Either way, buying those three LPs individually would run you circa $114 (or more), as opposed to the flat $110 for the Miles 55 box. Given the decade-old Quintet / Sextet LP that doesn’t appear to be part of the current Kevin Gray lacquer-cutting round, the i>Miles 55 box is the better overall cumulative bet, in our opinion.

As far our ratings go, the Music contained in Miles 55: The Prestige Recordings 180g 3LP box set garners an easy 9, while the Sound is a solid 8, given these are older monaural recordings at their root.

Pricing aside, a big appeal of the Miles 55 box set is convenience, as it contains all of this particular period of Davis’ music in one classily packaged place, simplifying the process of taking that deep dive into a crucial crossroads moment in his career. At the end of the day, the decision for making this sort of box set purchase is personal. If you don’t want to hassle with tracking down those three individual albums, a nicely curated collection like Miles 55: The Prestige Recordings is a super-handy way to immerse oneself into this seminal artist’s emerging moment in time.

Author bio: Mark Smotroff is an avid vinyl collector who has also worked in marketing communications for decades. He has reviewed music for eCoustics, among others, and you can see more of his impressive C.V. at LinkedIn.

One quick, additional note regarding the box set’s title, though. Some outlets list it as being “Miles ’55” with the apostrophe contraction in place, but that designation appears nowhere on the exterior packaging, spines/sleeves, or the LPs themselves in such a manner — it only shows up in the headline for Ashley Kahn’s portion of the reprinted liner notes — so we are not including said apostrophe in how we represent the Miles 55 box set title here.

MILES DAVIS
MILES 55: THE PRESTIGE RECORDINGS
180g 3LP (Prestige/Craft Recordings)
MUSIC: 9
SOUND: 8

Original albums produced by Bob Weinstock
Original recordings engineered by Rudy Van Gelder, Van Gelder Studio, Hackensack, NJ
Compilation produced by Nick Phillips
Project supervision for Craft Recordings by Mason Williams
Mastered by Paul Blakemore at CMG Mastering
Vinyl lacquers cut and mastered by Kevin Gray, Cohearant Audio

LP1, Side A
1. I Didn’t
2. Will You Still Be Mine?
3. Green Haze

LP1, Side B
1. I See Your Face Before Me
2. A Night In Tunisia
3. A Gal In Calico

LP2, Side C
1. Dr. Jackle
2. Bitty Ditty

LP2, Side D
1. Minor March
2. Changes

LP3, Side E
1. Stablemates
2. How Am I To Know?
3. Just Squeeze Me

LP3, Side F
1. There Is No Greater Love
2. The Theme
3. S’posin’