“I went out and I said ‘Don’t let the bastards get you down,’ and she said ‘I’m not down,’ and she sang. It was very courageous. It just seemed to me wrong, booing that little girl out there, but she’s always had courage.”
As a songwriter, he strived to find a balance between the strictly personal and bigger concerns. Talking with CMT in 2009, Kristofferson said, “I think you have to make it work on a one-to-one level first, as if you’re talking right to the person, but you just hope that you’ve written it well enough that people can identify with it and that it works on other levels.” Of “Me and Bobby McGee,” he said, “I remember [songwriter] Vince Matthews said, ‘You’ve got such a good song going on, why do you have to put that philosophy in there?’” — meaning “Freedom’s just another word for nothing left to lose.” “And it turned out to be probably the most memorable line I ever wrote, so you’ve gotta take your friend’s advice with a grain of salt.”
In an interview with Variety‘s Chris Willman in the 2000s, he spoke about his views and how they were received by others. “I saw some book the other day called ‘Shut Up and Sing’ (by conservative talk show host Laura Ingraham), and my only feeling was: I am singing, dammit — shut up and listen!”