The Billie Holiday Albums Ranked

The life and career of jazz singer Billie Holiday has been the subject of many fictionalized and non-fiction show business stories. The tragic background to one of the best singers of her day has most recently been brought to the screen in THE UNITED STATES VS. BILLIE HOLIDAY (2021), so clearly, Holiday, who died in 1959 at age 44, is still relevant to many. As she should be. Holiday’s distinctive voice changed a lot over her 26-year recording career (from 1933 to 1959), and the reduction of her upper range towards the end of her life is attributed to her heavy use of alcohol and drugs. That yielded some contemporary criticism, but as I’ll get into, there’s a powerful quality to Holiday’s ever-raspier voice on her final albums. Those final records are among the 12 studio albums that Holiday released from 1952 to 1959, but the bulk of her career happened long before that. You see, the long-playing (LP) format on vinyl didn’t really take hold until the 1950s, and before that, music was primarily distributed for home use in the form of singles. The term “album” was developed because various compilations before the advent of the LP days bundled a number of singles (each with a side A and side B, so two songs each) to form a longer release. Many contemporary compilations were released during Holiday’s “singles years,” which ranged from 1933 to 1952. But with these “albums ranked” pieces, I tend to avoid compilations, which are collections of disparate tracks that don’t fully represent a concerted effort to craft a singular work, as an LP does. However, an understanding of Holiday’s career can’t be reached without listening to the vast amount of music released in that 19-year period, and the best way to approach that today is with the modern box sets LADY DAY: THE COMPLETE BILLIE HOLIDAY ON COLUMBIA 1933–1944 (2001) and THE COMPLETE COMMODORE & DECCA MASTERS (2009); both are on Spotify and streaming services. I’m certain there is more to find from that era, but that was the foundation I started from. And now, below, I’ve ranked the 12 “comprehensive” Billie Holiday LPs.

#12 — SONGS FOR DISTINGUÉ LOVERS (1958)

Favorite track: “Stars Fell on Alabama”

To start, I’d like to clarify something about Billie Holiday’s contribution to music. Holiday’s vocal style is attributed to a shift in tempo and delivery in popular music, and by today, it has been emulated, honored, and parodied in equal measure, perhaps without direct knowledge. Billie Holiday has a quintessential “jazz oldies” voice to the modern ear, and by extension, the instrumentals backing her do too. While popular music and jazz had shifted significantly in sound from 1933 to 1959, the scope of Holiday’s career, the ’50s albums in particular may be difficult to distinguish for some. That was kind of the case for me, and I’ve listened to all of these albums many times. Billie Holiday definitely had her sound, and besides semi-significant shifts at key periods in her career, she never fully reinvented her musical style. And this can at least partly be attributed to the music industry of the day; Holiday was not a singer-songwriter as we know it today (although she did write a number of songs), and collaborated with and was backed by bands that had comparable credit for creating the sound of the “Billie Holiday albums.” Learned music theorists and players may disagree with me here, but the fact remains that many of Holiday’s albums don’t take on some new inspiration or strive for something markedly different, as we’ve come to expect from modern musicians. But that’s OK, because Billie Holiday, time and again, provided soothing, sad, wistful, and at times happy music within a jazz and blues framework. She undeniably did so with SONGS FOR DISTINGUÉ LOVERS, but what makes it Holiday’s “worst” album is harder to explain. Part of the process in ranking these albums was just evaluating the song choice for each; Holiday worked from jazz and pop standards and at times more modern songs, reinterpreted by her voice and bands. So part of the problem with SONGS FOR DISTINGUÉ LOVERS is that it just kind of has the worst track list of the ’50s albums, even if Holiday still sounds good on them. It was Holiday’s eighth album, and in being released just one year before her death, the singer’s voice does have the rough quality described by critics at the time and since. But it still has its plaintive, weary sound, and that is still resonant.

#11 — AN EVENING WITH BILLIE HOLIDAY (1953)

Favorite track: “Stormy Weather”

Although I explained that the LP format took hold in the 1950s, in the earlier part of the decade, the vinyl was manufactured in 10-inch size. This meant lesser playing time than we might expect today, so even though these early albums are considered “long plays,” they still clock in under 25 minutes or so. By the middle of the ’50s, the 12-inch format reigned supreme, and that was the standard until other media formats got rid of vinyl records. But when that 12-inch LP was still new, AN EVENING WITH BILLIE HOLIDAY, which was originally a 10-inch record, was augmented by some other tracks for a reissue entitled A RECITAL BY BILLIE HOLIDAY (1956). In my writing for this entry, I’m referring only to the 1953 release, as the extra tracks for RECITAL had also already been featured on the Holiday’s self-titled release from 1954. In any event, AN EVENING WITH was her second LP, and while the singer was by no means a sophomore 20 years into her recording career, I guess that kind of makes it a sophomore slump. But, again, that’s in part due to the song selection. By 1953, Holiday’s voice had taken on a new tone different than the one of 15, or ten, or even five years earlier. But it still wasn’t quite in the state it would be in by the end of the ’50s and Holiday’s life. While I think her voice never “got bad,” I can appreciate the difference between its sound on AN EVENING WITH and LAST RECORDING, for example. But I simply find the tracks on this album not as compelling, although “Stormy Weather” is great.

#10 — LAST RECORDING (1959)

Favorite track: “Don’t Worry ‘Bout Me”

Speaking of LAST RECORDING: as you might be able to guess, this was Holiday’s last album. Simply titled BILLIE HOLIDAY upon its original release, just earlier in the month of the singer’s death in July 1959 (confusingly, since there was a previous self-titled released five years earlier), LAST RECORDING does carry a significantly weakened version of Holiday’s voice. Perhaps it’s the retroactive significance as the “last recording” and the album’s accompanying dark cover, but there is something stirring about the plaintive straining of Holiday’s vocals. It’s augmented by the arrangement and production of Ray Ellis, who Holiday worked with to attempt to “sound like Sinatra.” I think that was essentially achieved for LAST RECORDING, which carries the mellow pop sound of Frank Sinatra’s recent successes IN THE WEE SMALL HOURS (1955) and FRANK SINATRA SINGS FOR ONLY THE LONELY (1958). So in terms of that difficulty in distinguishing the theses or unique style of each Billie Holiday album, LAST RECORDING actually stands out. But in spite of its, again, perhaps undeserved significance and artistic limitations pivoted into a strength, Holiday’s final record doesn’t carry many tracks that stuck with me. “Don’t Worry ‘Bout Me” is a notable exception.

#9 — BILLIE HOLIDAY (1954)

Favorite track: “Autumn in New York”

The singer’s third album and the last in the 10-inch era, the self-titled BILLIE HOLIDAY is indicative of the improving quality of track lists as I move through this list. While the songs themselves are stronger here, Holiday’s voice is also still in good form, although certain notes warble with a bit of uncertainty. I think it makes the tracks beautiful, though, especially “Autumn in New York.” Although every one of Holiday’s albums is sentimental and at least a little bit sad, I think BILLIE HOLIDAY carries a particularly wistful tone through the natural and colorful themes of some of its songs: “Moonglow,” “If the Moon Turns Green,” “How Deep Is the Ocean?,” “What a Little Moonlight Can Do,” and yes, “Autumn in New York.” The prevalence of moon imagery does cast a brilliant shadow on things.

#8 — VELVET MOOD (1956)

Favorite track: “I’ve Got a Right to Sing the Blues”

Holiday had a busy 1956, which saw the release of four albums. Well OK, two of those were reissues of her 10-inch LPs for the 12-inch format, but still. VELVET MOOD was one of the two original records of the year, and besides its beautiful cover (Holiday’s albums always had good covers), it’s also a pleasant listen. The album is a little swingier than the releases to come from Holiday in the late 1950s, but still beautifully lowkey. Much of the narrative surrounding Holiday’s career, overlooked because of her solo credit status and incredible life, concerns the greatness of her backing bands. After being associated with Teddy Wilson, Count Basie, and Paul Whiteman earlier in her career, Holiday was still able to command competent and brilliant studio musicians. They sound great on VELVET MOOD, and while Holiday’s voice is always the focal point on her albums, the instrumentals almost overpower her on this record. It may just be a mixing thing, but it’s also not unwelcome.

#7 — BODY AND SOUL (1957)

Favorite track: “Body and Soul”

BODY AND SOUL’s positive distinguishing characteristics are difficult to articulate (yada yada broken record yada yada), especially for this writer who has written about music extensively and yet is not trained well enough to really identify singular technical traits about it. But I do know that the impression of BODY AND SOUL is a relaxing listen, one that still engages with its songs of love and regret. I can also acknowledge that by this time, and supported by the 12-inch LP format, the singer was able to go a bit long on the tracks themselves, evidenced by the title track especially. I suppose it is a “middle of the road” Billie Holiday album (although she never made any bad ones), so it hits the expectations of such without exceeding too much.

#6 — STAY WITH ME (1958)

Favorite track: “Everything Happens to Me”

STAY WITH ME benefits from its song selection, a trait I’ve already identified and reiterated as a major part of the relative success of each of Holiday’s albums. Like BODY AND SOUL, STAY WITH ME also allows the singer to, well, breathe on each track; its seven tracks are stretched out across a nearly 34-minute run time. This contributes to a leisurely piece that, while playing with an easing energy, also allows the blues to settle in. “Everything Happens to Me” is the best example of that, and it actually augments Holiday’s part with extended instrumental-only sequences. That dynamic is reflected across STAY WITH ME, and it’s a weightier experience as a result.

#5 — ALL OR NOTHING AT ALL (1958)

Favorite track: “Speak Low”

While I’ve described entries in Holiday’s discography as quite similar, ALL OR NOTHING AT ALL is one of the most unique albums within it and, clearly, one of the best. “Speak Low” is the most unique track on this unique album, which is based fundamentally on a really fun and funky guitar part before transitioning into a great piano solo. With its 12 tracks, ALL OR NOTHING AT ALL is also able to explore a wider range of themes, emotions, and sounds. To be clear, this album is not a totally out-of-character release from Holiday. But it does also represent, as her third-to-last album, an effort from the singer to try some slightly different things, and I think that started with ALL OR NOTHING AT ALL.

#4 — LADY IN SATIN (1958)

Favorite track: “Violets for Your Furs”

LADY IN SATIN followed ALL OR NOTHING AT ALL and was Holiday’s penultimate album and the first of two collaborations with arranger Ray Ellis, which culminated, as described above, with LAST RECORDING. Holiday also returned to label Columbia, who she recorded for from 1933 to 1944. This meant that LADY IN SATIN was as marked a shift as Holiday made throughout her 1950s career. In returning to Columbia, working with classic pop standards, and directing Ellis to work with an orchestra in developing a Sinatra-like sound in contrast to the small jazz band sound she had cultivated across her previous ten albums, Holiday was trying to do something different with LADY IN SATIN. And it worked. Her voice still has that strained quality that I love but also that brought her some lukewarm reception. While it’s clearly not my favorite album by Billie Holiday, LADY IN SATIN may be her most ambitious.

#3 — MUSIC FOR TORCHING (1955)

Favorite track: “It Had to Be You”

As the first of Holiday’s 12-inch albums, following three in the 10-inch format, MUSIC FOR TORCHING had a little bit more time to work with. Therefore, its track list of torch songs were given ample room to simmer. Holiday was a renowned practitioner of the torch song, which rues lost or unrequited love, usually in a jazzy template. So a whole record of the things is true to a lot of what made Billie Holiday special, and besides that, the songwriting hooks across MUSIC FOR TORCHING’s eight tracks are among the strongest on any Holiday album. The record’s instrumentals toe the line of real lowkey energy and soaring emotions, the perfect musical representation of the spirit of the torch song.

#2 — BILLIE HOLIDAY SINGS (1952)

Favorite track: “Solitude”

Holiday’s first album is nearly her best. The singer came to the LP format, albeit in its 10-inch form, with all the hits. No, really. On BILLIE HOLIDAY SINGS, Holiday performed renditions of many of the big songs from her career in the 1930s and ’40s. The album would be reissued on 12-inch vinyl in 1956 as SOLITUDE, which is fitting, because that song (“Solitude”) is the best track on BILLIE HOLIDAY SINGS. It’s just wonderfully moody, and as Holiday’s first LP, the whole record is the closest to the vocal quality the singer was known for in the previous two decades. There is no filler on BILLIE HOLIDAY SINGS; all eight of its tracks are among Holiday’s best. Although prior recordings of its songs may serve you better, the small scale of Billie’s backing band and her matured voice form a nearly perfect nexus.

#1 — LADY SINGS THE BLUES (1956)

Favorite track: “Strange Fruit”

LADY SINGS THE BLUES was my first Billie Holiday album, and its version of “Strange Fruit” the first track from the artist I really remember hearing. Nearly 20 years before the release of Holiday’s sixth LP, she had faced some controversy and career upheaval for her first recording of the anti-lynching song. It is a powerful protest song from a time before that was fully considered a concept, and on LADY SINGS THE BLUES, Holiday returns to it with a weary maturation affecting her voice and, presumably, her very self. The record was considered a companion piece to her autobiography of the same name, and so there may be a bit more personal significance to the song selection on LADY SINGS THE BLUES; the title track, for example, was co-written by Holiday. While much of the album isn’t a confessional in the way we see modern musicians create them, LADY SINGS THE BLUES is a potent refinement of Holiday’s 1950s status and voice. Known by then for her life and career troubles and the subsequent impact on her vocal delivery, Holiday stays in a bluesy space that, even while turning to love songs like “Too Marvelous for Words,” is cemented by other tracks like the aforementioned “Solitude” and “Lady Sings the Blues,” in addition to “Good Morning Heartache” and “Willow Weep for Me.” LADY SINGS THE BLUES is a perfect entry point into Holiday’s enduring appeal, even in its place 23 years after her recording start and three years before her career and life’s end. For better and worse, Billie Holiday is now defined by those later years, of which this record is her finest work of art.