Top 10 Billie Holiday Albums (2024)

Photo: Unknown author, Public domain, via Wikimedia Commons

The most legendary of all jazz singers, Billie Holiday’s life story has sometimes overshadowed her music. Her personal life has been fictionalized in two major movies (Lady Sings The Blues and The United States Versus Billie Holiday), details about her have been sensationalized, and she has been cast as a symbol of her era even though, beyond her musical talents, her life (even with its dramatic episodes) was actually not that unusual for an African-American performer of the mid-twentieth century.

She was born as Eleanora fa*gan on Apr. 7, 1915 in Philadelphia. Her parents were teenagers and never got married; her father Clarence Holiday, who deserted the family, later played guitar and banjo with the Fletcher Henderson Orchestra. She had a very difficult childhood, dropping out of school when she was 11 and working at odd jobs. But after hearing recordings by Louis Armstrong and Bessie Smith, she knew that she wanted to eventually become a singer.

Changing her surname to her father’s with “Billie” coming from her admiration for actress Billie Dove, she began performing in clubs when she was 14 in 1929. Four years later, the young record producer John Hammond heard Holiday and arranged for her to record two numbers with a pickup group led by clarinetist Benny Goodman: “Your Mother’s Son-In-Law” and “Riffin’ The Scotch.” Those selections did not create much of a stir and Holiday later commented that her voice sounded so high, but they do show her already displaying her behind-the-beat phrasing.

1935 was the breakthrough year for the 20-year old singer. After making her first film appearance in a Duke Ellington short (Symphony In Black) during which she sings a chorus on “Saddest Tale,” she began her renowned series of recordings with pianist Teddy Wilson.

# 1 – Lady Day – The Complete Billie Holiday On Columbia 1933-1944 (Columbia/Legacy 1933-44)

The 1935-42 period was probably the happiest time in Billie Holiday’s life. She became a major name in jazz and an influential force. Although she mostly stuck to interpreting lyrics (she was never a scat singer or a powerhouse singer like Ella Fitzgerald or Sarah Vaughan), her phrasing reminded many listeners of horn players and she had an air of spontaneity about her singing that has long appealed to a countless number of listeners, At first some songwriters did not care for the liberty of her phasing but eventually her way of vocalizing caught on.

During this period she became close friends with tenor-saxophonist Lester Young, an individualist with a cool tone who called her “Lady Day.” She countered that by naming Young “Pres” or “Prez” since she considered him the president of the tenor.

While Holiday had stints with the big bands of Count Basie and Artie Shaw, because she was signed to a different record label, all that exists of her Basie period are three songs from radio broadcasts, while her lone recording with Shaw (“Any Old Time”) had to be withdrawn due to conflicts with their labels.

Billie Holiday’s recording career can easily be divided into three. She had separate periods in which she mostly recorded for Columbia-owned labels, Decca, and Clef (later reissued on Verve). During 1935-42, Holiday recorded regularly for such Columbia labels as Brunswick and Vocalion. At first she was featured on sessions led by pianist Teddy Wilson that had her taking a chorus in all-star swing combos next to some of the top soloists of the era. Starting in 1937, she also recorded as a leader with similar groups, but this time getting to open and close each performance with a chorus.

Always a quietly expressive singer, during this period Lady Day mostly sounded quite happy. She was becoming famous and clearly having a good time recording three-minute gems with many jazz greats. These sessions have been reissued in various forms many times through the years. For those with the budget, the ten-CD box set The Complete Billie Holiday on Columbia is the way to go.

Included in the box are Holiday’s two 1933 recordings, her 152 selections with the all-star groups of 1935-42, 58 alternate takes, the two radio broadcasts with Basie and one with Benny Goodman, and her appearance at the Esquire All-American concert of 1944. With the best swing soloists (including Lester Young, trumpeter Buck Clayton, Benny Goodman, and many others), Lady Day performs such gems as “What A Little Moonlight Can Do,” “I Cried For You,” “Billie’s Blues,” “I Can’t Give You Anything But Love” (during which her phrasing shows the Louis Armstrong influence), “This Year’s Kisses,” “I’ll Get By,” “Mean To Me,” “Foolin’ Myself,” “When You’re Smiling,” “If Dreams Come True,” “Them There Eyes,” “Swing Brother Swing,” “All Of Me,” and the original version of “God Bless The Child.” A special bonus is the 118-page book that comes with the box.

#2 – Control Booth Series, Vols. 1-2 (Jazz Unlimited, 1940-42)

A bit of a frivolity but something completists will want, these two single discs have all of the music recorded by Lady Day during her six sessions of Sept. 12, 1940-Feb. 10, 1942. Vol. 1 includes three additional takes that are not on the Columbia box while Vol. 2 has ten “new” alternates. While Holiday’s singing generally did not change much from version to version, some of the solos (particularly by Lester Young on the Mar. 21, 1941 date) are different each time.

#3 – Billie Holiday (Commodore, 1939-44)

In 1939 when Holiday was presented with the Abel Meeropol anti-lynching poem “Strange Fruit,” she immediately wanted to record it. When her record company balked, fearing a backlash from Southern customers, she was able to strike up a deal with Milt Gabler’s Commodore label to record “Strange Fruit” along with three less controversial numbers (including her classic “Fine And Mellow”). In 1944 when Lady Day was between labels, she recorded a dozen other numbers for Commodore. By that time she was considered a major star. She is very much in the spotlight and the group assembled by pianist Eddie Heywood is mostly in a purely supportive role behind her.

The single-disc Billie Holiday has all 16 selections that she made for Commodore including the original (and still sadly topical) “Strange Fruit,” “Embraceable You,” “Billie’s Blues,” “He’s Funny That Way,” “On The Sunny Side Of The Street,” and a touching version of “I’ll Be Seeing You.” For those who really want everything, there is a two CD set (accurately titled The Complete Commodore Recordings) that augments the 16 songs with no less than 29 alternate takes. But since there is relatively little solo space, much of that program is repetitive.

#4 – The Complete Decca Recordings (GRP/Decca, 1944-50)

Billie Holiday’s second period, which encompasses much of the 1940s, definitely had its ups and downs. Her voice was at its peak during the era, she had a prestigious association with the Decca label which sought to market her as a major star, and she appeared in her only Hollywood movie, New Orleans, playing opposite her early idol Louis Armstrong. On the minus side, Holiday had self-destructive relationships with men and became a heroin addict in the early 1940s, a plague that soon dominated much of her personal life. She was arrested and served a one-year jail sentence during 1947 that resulted in a lot of notoriety and her losing her cabaret card which made it difficult for her to work in New York clubs.

The two-CD Decca set features Lady Day in a wide variety of settings including with strings (“Lover Man”), combos, an orchestra, and even a vocal group. Despite the difficulty of her personal life, she is heard in top form throughout, with the highlights including “Don’t Explain,” “Good Morning Heartache,” “Easy Living,” “Solitude,” “My Man,” “’Tain’t Nobody’s Business If I Do,” “Crazy He Calls Me,” and a remake of “God Bless The Child.”

#5 – Billie’s Blues (Blue Note, 1942-1954)

Dropped by Decca in 1950, Holiday recorded four selections for the Aladdin label the following year including a memorable version of “Detour Ahead.” This single disc from Blue Note includes that date, a one-time collaboration with the Paul Whiteman Orchestra from 1942 (“Trav’lin Light”), and nine songs from an enjoyable concert in Germany from 1954. On the latter Holiday performs her usual repertoire with her trio and takes part in jam sessions versions of “Billie’s Blues” and “Lover Come Back To Me” with a larger group that includes clarinetist Buddy DeFranco and vibraphonist Red Norvo.

#6 – At Storyville (Black Lion, 1951-53)

Billie Holiday often appeared at George Wein’s Storyville club in Boston during the 1950s. This CD features her on two occasions in 1951 and once in 1953. Lady Day is in excellent form and three songs from 1951 have her joined for the only time by tenor-saxophonist Stan Getz.

#7 – The Complete Billie Holiday On Verve, 1945-1959 (Verve, 1945-59)

Lady Day’s third and final period should have been a happy one for her. She recorded in jazz-oriented settings for producer Norman Granz (often with Charlie Shavers or Harry “Sweets” Edison on trumpet and Flip Phillips or Ben Webster on tenor-sax), made good money going on Granz’s all-star tours, and was a household name. Her singing was often a bit autobiographical and she seemed to mean every word that she sang. But her heroin use continued, she drank and smoked excessively, and her voice declined steadily throughout the 1950s. While there are times when she sounded close to her prime, she was erratic and increasingly unreliable.

The ten-CD Vervebox set gives one a full picture of Billie Holiday during her later years and is a bit of a mixed bag. Most of the first disc has her singing at Jazz At The Philharmonic concerts from 1945-47. She sounds noticeably older during the 1952-57 combo dates but, even when she is off, her sidemen provide plenty of exciting solos. Her Carnegie Hall concert of 1956 (which celebrated the release of her memoirs Lady Sings The Blues) and her set at the 1957 Newport Jazz Festival have their moments but of lesser interest are a couple of recorded rehearsals, and the concert on the Blue Note album is repeated. Ending the large package is Billie Holiday’s final studio recording, an album from 1959 with arrangements from Ray Ellis that is better and more jazz-oriented than the more famous Lady In Satin set of the previous year

The complete Verve box is not really essential except to completists. More casual collectors should probably pick up some of the best of Holiday on Verve CDs that emphasize her work from the 1952-57 small group dates.

# 8 – Rare Live Recordings 1934-1959 (ESP, 1934-59)

This five-CD set is a treasure trove for Billie Holiday fans for it includes the cream of her live performances plus the soundtracks of her film and television appearances. One hears Lady Day on radio, on the Eddie Condon television show, at the Apollo Theater and Carnegie Hall, and at her last documented performances.

#9 – Banned From New York City – Live 1948-1957 (Uptown, 1948-57)

The material on this two-CD set is particularly rare, and surprisingly rewarding. Billie Holiday is featured with her trio and with the Red Norvo All-Stars at an enjoyable concert from 1948, singing a couple of duets with pianist Carl Drinkard in 1951, at concert and club appearances in 1954, on television in 1956, and on radio the following year.

#10 – Lady In Satin (Columbia/Legacy, 1958)

The most controversial of Billie Holiday’s recordings, Lady In Satin was her next-to-last album (not her final one as is frequently stated) and finds the 43-year old singer sounding as if she were 73. Backed by unimaginative string arrangements by Ray Ellis, Lady Day tries her best and is most effective on “You’ve Changed” and “I’m A Fool To Want You” But while her interpretations of these ballads are quite emotional and sometimes gut-wrenching, her voice is rarely up to the challenge. However, some listeners love this record for its intensity, and Lady Day was happy to be surrounded by strings this late in life.

Billie Holiday passed away on July 17, 1959 from cirrhosis of the liver at the age of 44. The performances on her Columbia and Decca collections show why she is still considered so important. Her best music is timeless.

Scott Yanow, jazz journalist/historian and author of 11 books including The Jazz Singers, The Great Jazz Guitarists, Trumpet Kings, Jazz On Film, and Jazz On Record 1917-76