One of the most innovative and influential vocalists in modern history, Eleanora Fagan (April 7, 1915 – July 17, 1959), better-known as Billie Holiday and famously nicknamed Lady Day, shaped the evolution of jazz and pop music. With her distinctive vocal delivery, inspired by jazz instrumentation, and her innovative manipulation of tempo and phrasing, she ushered in a new era of singing, popularizing jazz and enthralling wider and wider audiences.

Yet Holiday’s life was a far cry from following a smooth upward trajectory into stardom.

Raised by a single mother and raped by her neighbor at the age of eleven, she spent her early teens running errands at a brothel in exchange for the chance to listen to Louis Armstrong and Bessie Smith records. Shortly after her mother became a prostitute in Harlem, so did Eleanora. She was barely fourteen. But in the darkness of those early years, she somehow found the light that would guide her life. It was in Harlem that she first began singing at night clubs, taking her stage pseudonym from the names of actress Billie Dove and musician Clarence Halliday, the man she’d grown up considering her father. In November of 1933, at the age of 18, Holiday made her recording debut after the influential jazz producer and civil rights activist John Hammond found himself mesmerized by her voice at Covan’s club on West 132nd Street.

It took more than half a decade for Holiday to reach mainstream success, which she did in 1939 with her rendition of “Strange Fruit” — the highly political song based on the lynching of Jewish schoolteacher Abel Meeropol. Holiday first performed it with great trepidation, partly in fear of political retaliation and partly because it reminded her of the injustice surrounding the death of her father, who she believed had been denied vital lung treatment due to racial bigotry.

Despite blossoming into critical acclaim, however, Holiday’s personal life was a whirlwind of turmoil. Openly bisexual, she bounced between numerous affairs with men and women, most notoriously with the glamorous Broadway actress Tallulah Bankhead. By the early 1940s, she was at the height of her career and was earning $1,000 per week, but had spiraled into addiction and was spending nearly all her income on drugs. Over the decade that followed, despite having become commercially successful, her drug use, drinking, and tumultuous relationships with abusive men gradually but steadily eroded both her health and her ability to ability to defend her professional standing as she was being progressively defrauded of her earnings.

Still, her talent and her passion for singing were never questioned. In 1958, Frank Sinatra called her “unquestionably the most important influence on American popular singing in the last twenty years.” The following year, Holiday’s addiction finally claimed her and she died of heart failure caused by alcoholism-induced liver cirrhosis. Though she only had $0.70 in the bank at the time of her death, her imprint on music history remains priceless and inextinguishable. In 1973, Holiday was posthumously inducted into the Grammy Hall of Fame, reminding us that talent and tragedy may go hand in hand but the height of the human spirit transcends the tragic.

Learn more: Wikipedia | Lady Sings the Blues (1956 autobiography) | Billie Holiday (1995 biography)

Mexican painter Frida Kahlo (July 6, 1907 – July 13, 1954) remains best-known for her vibrant self-portraits, which comprise 55 of her 143 paintings and combine elements from traditional Mexican art with a surrealist aesthetic. This dual mesmerism with indigenous Mexican culture and the spirit of the new imbued Kahlo’s entire sensibility – she even insisted on stating July 7, 1910 as her birth date, rather than the correct date her birth certificate reflected, in order to make her birth coincide with the start of the Mexican revolution and thus align her life with the dawn of modern Mexico.

Kahlo was befallen by a disproportionate amount of medical misfortune. As a young child, she contracted polio, which prevented her right leg from developing fully – an imperfection she’d later come to disguise with her famous colorful skirts. As a teenager, while studying at Mexico’s prestigious Preparatoria school as one of only thirty-five girls, she was in a serious traffic accident, which left her with multiple body fractures and internal lesions inflicted by an iron rod that had pierced her stomach and uterus. It took her three months in full-body cast to recover and though she eventually willed her way to walking again, she spent the rest of her life battling frequent relapses of extreme pain and enduring frequent hospital visits, including more than thirty operations.

It was during her time in recovery that Kahlo first began painting, at first as a way of occupying herself while bedridden. Her mother even had a special easel made for her in order to be able to paint in bed with her father’s set of oil paints and brushes.

“I paint myself because I am so often alone and because I am the subject I know best,” she famously reflected on her self-portraits.

Two years after the accident, in 1927, she met the painter Diego River, whose work she’d come to admire, and he went on to encourage and mentor her work. In 1929, despite her mother’s protestations, the two were wedded and one of art history’s most notoriously tumultuous marriages commenced. Both had multiple affairs, the most notable of which for bisexual Kahlo were with French singer, dancer, and actress Josephine Baker and Russian Marxist theorist Leon Trotsky.

Despite her work being inducted into the world’s most prestigious art institution when the Louvre purchased one of her self-portraits in 1939, Kahlo didn’t reach wide critical acclaim until the early 1980s and the advent of the Neomexicanismo movement. Previously, she had been frequently reduced in historical accounts to “Diego Rivera’s wife.” Today, her work endures as one of the most prominent and singular voices in twentieth-century art.

In her final days, shortly before turning 47, Kahlo wrote in her diary, “I hope the exit is joyful — and I hope never to return.”

Learn more: Wikipedia  |  Smithsonian Magazine

American cartoonist and author Lynda Barry (born January 2, 1956) is as much a storyteller as she is a visual philosopher. From her 1999 graphic-novel-turned-off-Broadway-hit The Good Times Are Killing Me, exploring the interracial relationship between two girls, to her long-running, deeply empathic weekly comic strip Ernie Pook’s Comeek, Barry’s instantly recognizable works are invariably imbued with equal parts humor, irreverence, sensitivity, and wisdom.

In 2009, her graphic novel What Is, published the previous year, received an Eisner Award for Best Reality-Based Work. But perhaps the most remarkable quality of Barry’s work is precisely its defiance of reality — the whimsy and wit with which she blurs the line between the real and, to borrow Sartre’s term, the irreal to peel away at some simple truth or grand complexity of what it means to be human.

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When 23-year-old Sister Rosetta Tharpe (March 20, 1915 – October 9, 1973) first walked into the recording studio in 1938, she likely didn’t dare imagine that she would one day be celebrated as gospel music’s first superstar. The godmother of rock and roll. “The original soul sister.” But that’s precisely what the talented singer and electric guitarist went on to become, bridging the spiritual lyricism of gospel with the secular allure of rock and roll arrangements.

With her unique singing style and electrifying stage presence, Sister Rosetta has influenced a range of beloved musicians, including Elvis Presley, Aretha Franklin, Johnny Cash, Jerry Lee Lewis, Bonnie Raitt, and The Noisettes.

In 1998, the United States Postal Service honored Tharpe with a commemorative stamp. In 2003, a dozen contemporary musicians recorded the tribute album Shout, Sister, Shout!. In 2007, Tharpe was inducted into the Blues Hall of Fame.

Learn more: Wikipedia  |  NPR  |  Literary Jukebox