The Many Faces of Billie Holiday

A collection of Billie Holiday photos, posters, album covers, and videos  plus a selection of Kim Nalley performances of Billie’s songs.

Billie’s first album (1947) was preceded by 39 singles starting with “Riffin’ the Scotch” in 1934.

We have included looks at images by several photographers who worked with Billie, her trend-setting fashion choices, the musical friends, great concerts and finally her arrests for drug use and her untimely death at age 44. But the main focus is the music with as many clips as we could find. When we ran out of video we inserted a link with over three hours of her music for you to listen to while you look. There are also links to excellent articles and resources.

Read jazz singer and scholar Kim Nalley’s review of Billie

Read jazz pianist Richard Fregulia’s review of Billie.

Two Years Old (1917)

Kim Nalley sings “God Bless the Child.”

Summer 1932, 17 years old


                                     A complete Billie Holiday discography.


We have included two previous documentaries on Billie Holiday that include many excellent images and clips though rarely do they play the complete songs as we have provided here. Image quality varies on all videos as many come from early once-thought-lost short films and television kinescopes filmed off a television screen.


April 12, 1935








January 16, 1938

Recording The Man I Love, 1938

Gjon Mili is best known for the photographs he took for Life Magazine . 

A terrific selection of his work can be seen here too. He specialized in artists (his Picasso painting with light are iconic), musicians and other celebrities. A special interest in jazz resulted in stunning images with Duke Ellington, Dizzy Gillespie, Josh White, Mary Lou Williams, Gene Krupa, James P. Johnson, Count Basie, and Billie Holiday. In 1944, he directed the short film Jammin’ the Blues. 

Billie Holiday singing Fine & Mellow in photographer Gjon Mili’s New York studio, the scene of many jam sessions. Cozy Cole on drums, James P. Johnson at the piano, 1941

In the last week of September 1943 Life magazine sponsored a Jam Session in the studio of photographer Gjon Mili at 6 E23rd. Street New York City. Many great jazz musicians were present including Duke Ellington, James P. Johnson, Mary Lou Williams, Teddy Wilson, Sid Catlett, Jess Stacey, Eddie Condon and many more. The music was recorded for possible issue on V-discs but is never released. Billie’s photographs were published in a center spread of October 11th. issue of Life Magazine.

Cafe Society nightclub, NYC, 1947. Photo by Gjon Mili


at Cafe Society

“With few exceptions, every major pop singer in the U.S. during her generation has been touched in some way by her genius. It is Billie Holiday who was, and still remains, the greatest single musical influence on me.” Quoted from “The Way I Look at Race, by Frank Sinatra in the July, 1958, issue of Ebony.

Sinatra signing an autograph for Holiday in the 1940s

“Frank Sinatra and Billie Holiday: They Did It Their Way” by Jody Rosen in the New York Times.

‘‘Lady in Satin’’ (1958), an homage to Sinatra’s Capitol Records concept albums.


In the recording studio for Lady in Satin; photo by Don Hunstein in December, 1957

“Frank & Billie & Lester’s Mutual Admiration Society” on the Joys of Jazz podcast.

Billie performed “Fine and Mellow” in The Sound of Jazz on CBS TV.

You can watch the complete show.

Check here to see playlist and who played which songs.

Read Thomas Cunniffe’s Interactive Essay on The Sound of Jazz.

Outside the Apollo Theater, 1952

The film New Orleans with Louis Armstrong, Zutty Singleton, Barney Bigard, Kid Ory, Bud Scott, Red Callender & Charlie Beal.

CIRCA 1970: Photo of Billie Holiday Photo by Michael Ochs Archives/Getty Images



Watch the entire New Orleans film with a lot more of great Louis Armstrong music.


The perfect follow up to Billie is the hour long Strange Fruit, exploring the history and legacy of the Billie Holiday classic written by Abel Meeropol. The song’s evolution tells a dramatic story of America’s radical past using one of the most influential protest songs ever written as its epicenter.

You can rent it here

Amy Goodman discusses the film on Democracy Now.

Animated interpretive short.

Listen to an NPR audio documentary.

The Kennedy Center presents their “Of Thee We Sing” with a focus on “Strange Fruit.”

Andra Day as Billie Holiday on the upcoming biopic, The United States vs. Billie Holiday

The Precious director’s The United States vs. Billie Holiday was released in 2021 by Paramount Pictures on Hulu. Daniels was influenced by Lady Sings the Blues (1972) starring Diana Ross. Written by Pulitzer Prize winner Suzan-Lori Parks, it stars Grammy nominee Andra Day as the jazz great. While Lady Day was beloved by fans in the U.S and overseas, the Federal Bureau of Narcotics, was determined to silence her. Holiday was ordered to stop singing her anti-lynching song, “Strange Fruit,” which served as a call to action for the Civil Rights Movement. The singer refused to oblige the authorities and a sting operation was set up. 

Director Daniels said: “With the world’s eyes forced to look at the centuries-old oppression of Black people, I hope The United States Vs. Billie Holiday will add to this important conversation by shining a light on systemic racism and social injustice. I also feel that in this time of great reckoning it is essential we celebrate the life and artistry of an unsung Civil Rights warrior, Billie Holiday.”

While Day is excellent the film feels exploitative and manipulative.

Day talked about portraying Holiday on NPR’s “All Things Considered.”

Read more and see stunning photos in Essence and Vanity Fair.



Billie Holiday fooling around backstage with Spizzy Canfield, 1946 Photo by John W. Mosley



Billie Holiday featured on Stars of Jazz on August 13, 1956, a TV program hosted by Bobby Troup. Here, she sings in order “Please Don’t Talk About Me When I’m Gone”, “Billie’s Blues”, and “My Man”.

In 1957, two years before her death photographer Jerry Dantzic captured Holiday on and off stage for her engagement at New York’s 
Sugar Hill. In 2017 the book Jerry Dantzic: Billie Holiday at Sugar Hill features never-before-seen photographs. Read about it and see more images here

An exhibit curated by the Smithsonian Institute is currently on tour with 56 Dantzic photos. We present four of them below. 


Billie Holiday with Bernie Weissman, owner and manager of Sugar Hill, on Broad Street, Newark. Photo by Jerry Dantzic

At Sugar Hill. Photo by Jerry Dantzic

Holiday with Carl Drinkard on Broad Street, receiving a gift from a fan. Photo by Jerry Dantzic


Walking down Broad Street after a gig.Photo by Jerry Dantzic

This stamp is based upon a photograph taken by William Gottlieb in February 1947 when Billie was working at the Down Beat Club.

From the Phil Stern Archives

“One of Roy DeCarava’s most iconic photographs, this work communicates the legendary jazz singer’s personality as a person, not just a performer. DeCarava was dedicated to to portraying black people in a serious and in an artistic way, something he felt was lacking in art history. Here, the returned gaze affords Holiday dignity and the artist’s smokey black and white tones give the portrait formal coherence.”(Notes and photo courtesy of Artspace)

Billie at Braddocks, Harlem, 1952

Billie Holiday and Hazel Scott at a Party, 1957; Photo by Roy DeCarava

New York Times review of two recent books about DeCarava.

The official Roy DeCarava website.

David Zwirner Gallery represents the deCarava Estate and offers links to valuable articles and many photos. 

This video focuses on one of the two broadcasts that still exist of Lady Day on Art Ford’s critically acclaimed show, Jazz Party. Jazz Party, which debuted in May of 1958, was basically a ninety minute live television show showing the day’s top musicians basically in a jam session. Many people were regulars such as Coleman Hawkins, Ben Webster, and Billie herself. Billie was featured on the show four times, but there are only two broadcasts that survive, both from July of 1958. This particular broadcast is recorded exactly one year before Lady’s death on July 17, 1958.. The songs she sings are in order: “Moanin’ Low”, “Don’t Explain”, and “When Your Lover Has Gone”.

The songs she sings are in order: “Foolin’ Myself”, “Easy to Remember”, and “What a Little Moonlight Can Do”.

The Strand Theatre in Manhattan, New York City, advertising the film ‘Key Largo’ and an appearance by Count Basie and his orchestra, and singer Billie Holiday, 1948.

We have included all of the filmed performances of Billie that we could find and suggest you listen to an hour of classic recordings as you finish enjoying the gallery. She made many television performances but most were early live TV with no copies made.


Herman Leonard’s photographs of musicians are stunning and he especially captured Billie Holiday in a variety of moods.

His website has hundreds of images organized by the subjects.

The Morrison Hotel Gallery has a wonderful selection.

This 1949 photo released by Herman Leonard Photography, shows Billie Holiday cooking a steak for her dog Mister in her apartment in the Harlem neighborhood of New York. The photographer, Herman Leonard, said she came to the door wearing a simple house dress and an apron and “First I thought, this is the maid.” But it was Holiday, one of the greatest voices of modern time, whom Leonard would continue to photograph throughout her life.

Hollywood Bowl Jazz Festival, 1953





With Coleman Hawkins

Billie was known for her fashion sense with her purses, sunglasses, jewelry, furs, headwraps, dresses and, or course flowers. Read Vogue‘s “The Enduring Legacy of Billie Holiday’s Exquisite Style.”


Portrait of Billie Holiday (Photo by Carl Van Vechten Collection/Getty Images)

Photo by Carl Van Vechten 1949

Photo by Carl Van Vechten in 1949


Photo by Nat Singerman

Billie’s Style 101

  • Elaborate Hair Accessories. Billie was often photographed wearing her signature accessory: beautiful flowers which she pinned in her hair. 
  • Statement Jewelry. Never one to blend in with a crowd, Billie liked to wear lots of gorgeous, statement-making jewelry. She wore chandelier earrings, cocktail rings and strands of pearls for a lounge-like vibe which can easily be mimicked today.
  • Fancy Frocks. Even when she wasn’t performing, Billie always accentuated her curves with gorgeous, body-skimming dresses. Printed, lacy or bejeweled, Billie looked amazing in every dress she wore. 
  • Luxe Details. Whether she wore an oversized bow, a fur coat or a sequin-encrusted sweater, Billie knew how to make a statement with her wardrobe. She always wore pieces with that extra dose of pizzazz, which made her style anything but average.

1950, Los Angeles, California, USA — Billie Holiday, Sarah Vaughn, and Louis Armstrong – Photo Joseph Schwartz

Billie Holiday at record producer Harry Lim’s jam session, photographed by Life photographer Charles Peterson, c. 1939. See More from the session.

1949 ad


What a line-up! The concert was the biggest attraction in New York featuring all the greatest jazz stars and was a benefit for the Courier Charities Fund.

Billie Holiday, Miles Davis, Illinois Jacquet, Ella Fitzgerald and Joe Guy (who was Billie’s trumpeter, lover and drug supplier at the time) backstage at this concert.

Billie held a photo shoot while in the hospital. On March 22nd. 1947  Downbeat owner Rudy Breadbar decided to cut his losses and closed the club for the summer, leaving Billie temporarily unemployed. Manager Joe Glaser insisted that Billie attempt to break her drug habit at a new New York clinic, the Park West Hospital in midtown for a $2000 3-week cold-turkey cure. She has a photo of Louis by her bedside.

with Duke Ellington

Billie had problems with drinking and drugs. The FBI targeted her partially because of her singing “Strange Fruit” and because they heard that she took drugs. Another popular singer with similar addictions, Judy Garland, was treated very differently. She was white. Read Johann Hari’s  “The Hunting of Billie Holiday” in Politico Magazine.

PHILADELPHIA – MAY 20: Jazz singer Billie Holiday (R) is read the charge for heroin possession at the U.S. Commissioners Office, seated next to her are her pianist Bobby Tucker (C) and road manager James Asendio (R) on May, 20, 1947 in Philadelphia, Pennsylvania. (Photo by Michael Ochs Archives/Getty Images)

Jazz singer Billie Holiday mugshot in May 1947. (Photo courtesy Bureau of Prisons/Getty Images)


PHILA,.PA…“DOPE RAID.” Nightclub singer Billie Holiday was picked up by Phila., Police in an early morning dope raid at her hotel today. She was held under bail on charges of using dope. She is currently filling a singing engagement at a night club here. Held with her on the same charge was her husband and road manager, Louis McKay, 46. The 41-year-old singer insisted on bringing her pet Chihuahua dog to City Hall. Photo shows Billie leaving the Central cell with her pet dog. Detective Capt. Clarence Ferguson who lead the raid is behind her. DAILY NEWS PHOTO BY SAM PSORAS….2/23/56….

Jerry Stoll  captured many jazz musicians and the San Francisco Beat scene in the 1950s and 60s.

He was was Resident Photographer for the first eight years of the Monterey Jazz Festival and at the first one in 1958 photographed Billie backstage on Club Nite.

Also with her dog Pepi.

















Listen to “Billie Holiday At Monterey Black Hawk 1958” BKH50701-A 12inch LP: Side A; Side B        Set list. 

“This was Monterey’s first festival and Lady Day’s last. Though her voice was shot and her grasp on the notes uncertain, some of the emotional impact survived. All 11 tunes in these 30 minutes of music had been done in numerous earlier and superior studio versions. Waldron’s piano is subpar; Gerry Mulligan is very helpful on several tunes; Buddy De Franco is heard from marginally. Benny Carter’s name should not have been used here, since he is virtually unheard. The plane flying over the fairgrounds during one song is so intrusive you feel like ducking. By the standards of an artist who at her peak 15 years earlier was the consummate jazz singer, this is 3 1/2-star material.” Leonard Feather, Los Angeles Times

Program Book (Billie on page 48)

Milt Hinton was a legendary double bassist and photographer who captured his fellow performers in a way an outsider couldn’t.

Billie Holiday and Count Basie, television studio (Sound of Jazz rehearsal), New York City, 1957; Photo by Milt Hinton

Billie Holiday, recording studio (her last recording session), New York City, 1959

Billie Holiday at her last recording session, 1959 (Milt Hinton) Billie Holiday made her final studio recordings in New York at a session led by arranger Ray Ellis on March 11, 1959. With Milt Hinton on the bass. Holiday was ill during the recording and passed away four months later. Simply titled Billie Holiday. It included All The Way” is a 1957 song by Sammy Cahn, Jimmy Van Heusen. It was introduced by Frank Sinatra in the film The Joker Is Wild.


A portrait of Billie Holiday shows Hinton at his finest. Taken during one of her last recording sessions, the image portrays the singer in a deep and wistful contemplation, her head hangs down, lost in past memories. This powerful image when matched with the wall text tells the complete story. “As I watched Billy listening back to her last recording session, I noticed that her eyes filled up with tears and I had the feeling that she was imagining how she had sounded 20 years ago…” As fans of Holiday know, the singer’s heavy addition to drugs altered her iconic voice, so that by the end of her career, Holiday was only a shadow of her former self. 

Billie Holiday (later released as Last Recording, was her last album. Completed on March 11, 1959, four days later, her lifelong friend and music partner Lester Young died on March 15, 1959. She would die four months later on July 17, 1959, at the age of 44. he album cover photo is generally attributed to Milt Hinton.

Linear Notes by Leonard Feather

Milt Hinton website

The Milton J. and Mona C. Hinton Collection is at the Oberlin College.

Billie Holiday, with Teddy Wilson at the piano and Milt Hinton on bass, at the Newport Jazz Festival, July 1954; Photographer unknown


7/21/1959-New York, NY- Crowds mill around St. Paul the Apostle Roman Catholic Church as the casket of blues singer Billie Holiday is brought out following a solemn requiem mass. Miss Holiday died from heart failure brought on by congestion of the lungs. She had been hospitalized for more than six weeks.

The gravestone of jazz singer and songwriter Billie Holiday is viewed March 25, 2015 at Saint Raymond’s Cemetery in New York. Billie Holiday died with just $50 to her name taped to her thigh. AFP PHOTO/DON EMMERT

Photo by Herman Leonard

Visit and subscribe to the Official Billie Holiday Website

The Last Days of Billie Holiday by David Lobosco

For many wonderful images look at the Getty Images Archive.

The Enduring Legacy of Billie Holiday’s Exquisite Style: Photos

BILLIE HOLIDAY SONGS is a tribute to an exceptional and beloved artist. Here you will find lots of information – including lyricsdiscography, musicians, and all her songs.

For dozens of recordings and old radio shows visit “The Billie Holiday Experience.”

The Unofficial Billy Holiday Website

This fan site has a terrific chronology of photos and more. 





















Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s