Long before the phenomenon that was Amy Winehouse, whose mesmerizing voice captivated millions, there was Janis Joplin, to whom Winehouse was often compared. While Joplin only released three albums during her lifetime (and a few posthumously) and only one Top 40 hit, she still became one of the biggest American music stars of the 1960s, and her music continues to influence musicians today.

Joplin and her band, Big Brother and the Holding Company, first made a name for themselves at the 1967 Monterey Music Festival where she emerged a bright and talented star. Unfortunately, the lifestyle of a hard-partying ’60s rock star soon took its toll. Her love of whiskey brand Southern Comfort became as well known as her voice, just like other hard-partying bands like Led Zeppelin or eccentric personalities like Ozzy Osbourne. While the story of Janis Joplin’s passing in 1970 serves as a somber end to her tale, underneath her music-star persona, she was a sensitive soul who had been damaged by bullies and hurt by lovers, and who wanted to be loved simply because she couldn’t do it herself.

She Was Stood Up For A Three-Way The Night She Passed

Photo: ABC Television / Wikimedia Commons / Public Domain

Janis Joplin’s experiences with men – and how often she was hurt by them – are well-publicized, but Joplin, who was actually bisexual, had troubled relationships with women as well. She had an on-again-off-again relationship with Peggy Caserta that, in total, lasted longer than the combined relationships Joplin had with men.

When she passed, Joplin was engaged to Berkeley student Seth Morgan. On the night of October 4th, when she would later overdose, a three-way was scheduled between Joplin, Morgan, and Caserta, but both of her partners failed to show.

She Loved Southern Comfort So Much, The Company Gifted Her A Fur Coat

Joplin’s fashion sense, much like her voice, was distinctly her own and was often loud and mismatched. The Daily Texan, the campus paper at the University of Texas, ran a profile on Joplin in 1962, stating, “She goes barefooted when she feels like it, wears Levis to class because they’re more comfortable, and carries her autoharp with her everywhere she goes so that, in case she gets the urge to break into song, it will be handy.”

Another accessory she was never without was a bottle of the sweet, whiskey-flavored liqueur, Southern Comfort. Her obsession with the drink even earned her a free jacket; the Southern Comfort company was allegedly so pleased with all the free product placement, they gifted Joplin a lynx fur coat.

She Changed Her Will Two Days Before Her Passing

Joplin made adjustments to her will just two days before October 4th, 1970, when she passed away from an overdose. She mostly gave her estate to her parents, with some additional wealth going to her siblings.

She also asked for $2,500 to be set aside for her friends to throw a party in her honor. The stipulation allowed 200 people to hold an all-night gathering at her favorite pub, “so my friends can get blasted after I’m gone.”

Joplin’s ashes were scattered over the Pacific Ocean as well as along Stinson Beach in northern California.

She Was Arrested After One Of Her Concerts For Swearing Onstage

In March of 1969, Jim Morrison was arrested during a concert in Miami for allegedly exposing himself onstage. Following this historic incident, conservative Florida citizens were concerned when Janis Joplin came to Tampa the following November. As she was performing for a rowdy crowd at Curtis Hixon Hall, the lights in the auditorium were turned on to quell audience excitement. A few police officers climbed onto the stage and asked Joplin to help them quiet the crowd. She refused and instead screamed obscenities at the cops.

Eventually, the crowd quieted enough that the show could continue and Joplin was allowed to finish, unlike Morrison, who was arrested in the middle of his performance. Joplin was later arrested in her dressing room and spent the night in jail, but the charges were eventually dropped when a judge felt she was simply exercising her freedom of speech.

Leonard Cohen Wrote ‘Chelsea Hotel No. 2’ About Her

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Joplin once said of her lifestyle, “I live pretty loose. You know, balling with strangers and stuff.” Although she was very open about who she loved physically, she often suffered emotionally if she felt that one of her lovers was letting her down.

Joplin ran into musician Leonard Cohen in the Chelsea Hotel elevator in 1968, culminating in the two spending the night together. The affair was short-lived, however, and for Joplin, it apparently ended in heartbreak:

“Really heavy, like slam-in-the-face it happened. Twice. Jim Morrison and Leonard Cohen. And it’s strange ’cause they were the only two that I can think of, like prominent people, that I tried to…without really liking them up front, just because I knew who they were and wanted to know them. And then they both gave me nothing.”

Cohen wrote about the encounter in his classic song “Chelsea Hotel No. 2,” but didn’t admit it was about Joplin until many years after she had died. “She wasn’t looking for me, she was looking for Kris Kristofferson,” he recalled.

She’s A Member Of The Infamous ’27 Club’

Photo: Grossman Glotzer Management Corporation / Wikimedia Commons / Public Domain

After a doctor told her she wouldn’t reach 24 if she continued her indulgent lifestyle, Joplin was proud to prove him wrong.

Despite the trend of psychedelics usage popular in the ’60s and ’70s, Joplin’s primary vice was alcohol. She did, however, develop a heroin addiction in the mid-1960s. Her usage steadily worsened, and by 1969, she was allegedly using approximately $200 worth of heroin every day. After some of her friends intervened, she eventually managed to quit the habit, only to relapse later.

On October 4, 1970, she was scheduled to record vocals for a track called “Buried Alive in the Blues,” a song that was slated to appear on her upcoming solo album, Pearl. When she never arrived at the recording studio, she was eventually found deceased in her hotel room from an apparent heroin overdose.

Joplin’s death at the age of 27 made her a member of the “27 Club,” a list containing other artists who passed away at the same age, including Jim Morrison, Jimi Hendrix (who died only 16 days after Joplin), Kurt Cobain, and Amy Winehouse.

Being Voted ‘Ugliest Man On Campus’ In College Left Her With Lasting Emotional Scars

Photo: Ashley Famous Agency / Wikimedia Commons / Public Domain

Janis Joplin was not considered by many to be conventionally pretty, and because of this, in addition to weight and acne issues from her youth, she struggled with her self-esteem for her entire life.

As a child, Joplin was bullied for her appearance and “different” behavior, and this abuse continued all the way through college at the University of Texas in Austin. A fraternity voted her “Ugliest Man on Campus,” hurting her deeply and leaving scars she never forget. Joplin dropped out of college and left Texas for San Francisco to escape the “angry men who liked to pick on her.”

She Bought A Headstone For Bessie Smith

Photo: Albert B. Grossman Management / Wikimedia Commons / Public Domain

Although she spent a number of years playing folk music, the blues was the genre for which Joplin had the most passion. “I want to be the first black-white person,” she once said. Billie Holiday, one of the most beloved voices of the blues genre, was considered a hero of Joplin’s. Joplin cherished Holiday’s autobiography, Lady Sings The Blues, her entire life, possibly because of the many parallels between the two artists.

Perhaps even more noteworthy than her love for Billie Holiday was Joplin’s devotion to Bessie Smith. She claimed Smith was her biggest influence and inspiration, and that she felt such a connection to Smith that she even believed she might be her reincarnation. Smith was buried in an unmarked grave because her family refused to pay for a grave-marker. When Joplin discovered this, she was so angered that she paid for a tombstone along with the daughter of one of Smith’s employees. They epitaph, “The Greatest Blues Singer in the World Will Never Stop Singing,” was engraved on Smith’s headstone.

Joplin Was Ostracized In School For Her Belief In Desegregation

Photo: Elliot Landy / Wikimedia Commons / CC BY-SA 4.0

While Joplin was growing up in Port Arthur, Texas, the town was racially segregated. Joplin’s strong support of desegregation – which she developed in part thanks to her parents’ affinity for art, literature, and learning – set her apart from her classmates and provided further incentive for them to bully her. She suffered frequent name-calling and would skip classes to avoid her tormenters, only attending enough to successfully graduate. “They laughed me out of class, out of town, out of the state,” she said after moving to California.

Her proud stances against segregation also came from a love of folk and blues music which she later used as influences for her own songs.

She Often Ditched Clothes In Photos And Onstage

Photographer Bob Seidemann wanted to use a picture of Joplin to make a statement about the idealism of hippie culture and asked her if she’d pose topless. Joplin decided she’d rather pose completely naked, despite Seidemann telling her that wasn’t necessary. “That’s the way she was. She wanted to take her clothes off real bad,” he remembers.

A concert promoter at Pittsburgh’s Civic Arena recalls an incident in which she was late to the stage because she was having sex in her dressing room. When she finally emerged, he was horrified by her outfit. “When I got there, Janis was finally walking up to the stage. She wore a sheer netted skirt with no underwear. When the spotlight hit her, you could see everything,” he noted.

She Broke A Bottle Over Jim Morrison’s Head

Since Janis Joplin and Jim Morrison were two of the biggest music stars of the 1960s, their eventual meeting was inevitable. Producer Paul Rothchild invited them both to a party where, while they were both sober, they hit it off. Once the two started drinking, however, Joplin remained pleasant and fun-loving while Morrison became obnoxioius and even violent. Joplin was so turned off, she left. After her rejection, Morrison followed her until Joplin hit him over the head with a bottle of Southern Comfort, knocking him out.

Despite her disinterest, Morrison was still determined to win her over, asking Rothchild for her phone number. Joplin never complied.

She Had Good Grades In School And Was Close With Her Parents

Photo: Thomas Jefferson High School / Wikimedia Commons / Public Domain

Although Joplin is remembered for her rebellious nature and free lifestyle, she had a softer, intellectual side as well. She loved to read, paint, and write poetry, and she always did well in school. Joplin also preserved a positive relationship with her parents, maintained correspondence with them throughout her life and career. Despite her participation in 1960s counterculture, she constantly sought their approval and cared for them deeply.