Janis Lyn Joplin (; January 19, 1943 - October 4, 1970) was an American rock singer and songwriter; one of the most successful and widely-known female rock stars of her era. After releasing three albums, she died of a heroin overdose at the age of 27. A fourth album, Pearl, was released in January 1971, just over three months after her death.

Joplin appeared at Woodstock starting at approximately 2:00 a.m., on Sunday, August 17, 1969. Joplin informed her band that they would be performing at the concert as if it were just another gig. On Saturday afternoon, when she and the band were flown by helicopter with the pregnant Joan Baez and Baez's mother from a nearby motel to the festival site and Joplin saw the enormous crowd, she instantly became extremely nervous and giddy. Upon landing and getting off the helicopter, Joplin was approached by reporters asking her questions. She referred them to Caserta as she was too excited to speak. Initially Joplin was eager to get on the stage and perform, but was repeatedly delayed as bands were contractually obliged to perform ahead of Joplin. Faced with a ten-hour wait after arriving at the backstage area, Joplin shot heroin and drank alcohol with Caserta, and by the time of reaching the stage, Joplin was "three sheets to the wind". During her performance, Joplin's voice became slightly hoarse and wheezy, and she struggled to dance.  Joplin pulled through, however, and engaged frequently with the crowd, asking them if they had everything they needed and if they were staying stoned. The audience cheered for an encore, to which Joplin replied and sang "Ball and Chain". Pete Townshend, who performed with the Who later in the same morning after Joplin finished, witnessed her performance and said the following in his 2012 memoir: "She had been amazing at Monterey, but tonight she wasn't at her best, due, probably, to the long delay, and probably, too, to the amount of booze and heroin she'd consumed while she waited. But even Janis on an off-night was incredible."  Janis remained at Woodstock for the remainder of the festival. Starting at approximately 3:00 a.m. on Monday, August 18, Joplin was among many Woodstock performers who stood in a circle behind Crosby, Stills & Nash during their performance, which was the first time anyone at Woodstock ever had heard the group perform with Neil Young. This information was published by David Crosby in 1988. Later in the morning of August 18, Joplin and Joan Baez sat in Joe Cocker's van and witnessed Hendrix's close-of-show performance, according to Baez's memoir And a Voice to Sing With (1989).  Still photographs in color show Joplin backstage with Grace Slick the day after Joplin's performance, wherein Joplin appears to be very happy. Joplin was ultimately unhappy with her performance, however, and blamed Caserta. Her singing was not included (by her own insistence) in the 1970 documentary film or the soundtrack for Woodstock: Music from the Original Soundtrack and More, although the 25th anniversary director's cut of Woodstock includes her performance of "Work Me, Lord". The documentary film of the festival that was released to theaters in 1970 includes, on the left side of a split screen, 37 seconds of footage of Joplin and Caserta walking toward Joplin's dressing room tent.

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