Janis Joplin commanded every crowd she was ever in front of, and every audience was captivated by her grit and her talent. With that and hits like “Try (Just a Little Bit Harder),” “Maybe,” and “Piece of My Heart” under her belt, she landed the headliner spot at the historical Woodstock ’69 despite initially not knowing of the existence of the music festival. Joplin’s set started in the late hours of Saturday, August 16, 1969, until the dawn of August 17 Sunday. Many of the festival-goers went for Janis as she was one of the major acts in the 40-band lineup.
She arrived with her band to Woodstock via helicopter on Saturday, August 16 but she didn’t expect the 500,000 people that would be there. Joplin had told her band that they were just playing just like another one of their usual gigs. She was shocked but giddy about the enormous crowd that would be watching her perform live. Though she was eager to get on stage and perform, she and her band had to endure a ten-hour wait as other bands were contractually obligated to perform her — her being the headliner of the weekend show.
It was said that during her ten-hour wait in the green room backstage, she drank booze and shot heroin with her lover Peggy Caserta. After Credence Clearwater Revival’s set, Joplin took the stage, high and drunk, but still killing’ it with her performances. She engaged the crowd, asking them if they had everything they needed and if they were staying stoned. On stage, she also sang what would be her biggest hit single posthumously, “Me and Bobby McGee”, to which she introduced her as a project she did with producer and songwriter Kris Kristofferson. “Me and Bobby McGee” would be included in Pearl, her second and final solo studio album released posthumously, a year after her untimely death due to a drug overdose.