In the spring of 1970, Kris Kristofferson played at the Bitter End in Greenwich Village, and Bobby Neuwirth had liked his act so much that he brought his friends to see him. Bobby offered to introduce Kris to Janis, suggesting that they hop on a plane immediately and fly to the West Coast. When Neuwirth called Janis she was ready to party and when he told her he had a buddy with him, she told him to bring him along. When they arrived at the party in Larkspur, Kris caught Janis' eye right away. "She thought he was a honey," Sunshine said. He was thirty-four years old and like her, a Texan. He'd hitchhiked around the country and spent years in Nashville, struggling to be a songwriter. His efforts where beginning to pay off when Roger Miller's recording of "Me and Bobby McGee" became a country hit. Johnny Cash recorded Kris' "Sunday Morning Coming Down," and began featuring him on his popular TV show.
Kristofferson and Neuwirth stayed with Janis in Larkspur for a couple of weeks. In that time, all of them hopped through the Sausakito bars and consumed unending amounts of alcohol. Janis often complained about people staying at her place, feeling that she was used for the benefits she could provide. "I'd a split there," Kris protested. "I dug her, but I had itchy feet. I'd get up intending to get out, and in she comes with the early morning drinks and pretty soon you're wasted enough and you don't care about leaving. She'd definitely let ya know when she was being abused, and she thought so a lot. She was always jangling around talking about how everybody was living off of her, but she had people she'd bring into the house and then she'd bitch because she was giving them bed and board."
"Kristofferson wanted her to cut 'Me and Bobby McGee,'" said James Gurley. "He was beginning to make waves with his own career. It's not like that would be his only motivation for hanging around her, but the money from a Joplin record would have come in handy." That spring Janis had a look at the song. "I remember when he introduced 'Me and Bobby McGee' to her," said Dave Richards, who was remodeling the house. "When I got there that day, she said, 'Listen to this song. This is a great song.' She was playing the guitar and sang 'Me and Bobby McGee' to me."
In the month preceding Janis' death, she had a conversation with Kris where she made a threat. "If it doesn't get any better," she'd warned, "I'm gonna go back on junk," and along with that had often talked of suicide. Kris had naturally become very upset, and Janis, in response, had retorted bitterly, "You won't be around. None of 'em will be." In a later conversation, the subject of dope came up. He said, "Man, you got everything going for you. You got a man you love; you got a producer you love. Chicks, artists, never have either one. Why blow it?" Janis said, "What's it all worth?"
After Janis' death, Kris Kristofferson broke down in the studio when he heard "Me and Bobby McGee." The song went on to become her only number one single.