When you think of Kris Kristofferson, which songs come to mind? What are the essential records? "Highwayman" immediately comes to mind, arguably his biggest song by far. "American Remains," or "Me and Bobby McGee" are massive honorable mentions as well. It's hard to really quantify a defining moment in his illustrious career. From his work to the fellow Highwaymen to his acting to his solo music career, he has an abundance to choose from. However, if it came down to one central record in particular, Kris Kristofferson had one record he would declare as his most definitive.
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In an interview with On the Tracks on October 1992, Kristofferson talked about performing at Bobfest. It acted as the "30th Anniversary Concert Celebration" for Bob Dylan, where he joined Stevie Wonder and Sinead O'Connor. In the interview, Kris highlights why he decided to pick the song "I'll Be Your Baby Tonight" to play. When it comes to highlighting what Dylan was all about, it felt right because that was the song he felt was most important besides "Help Me Make It Through the Night."
Kris Kristofferson Reveals One of The Most Important Songs in His Career
"'I'll Be Your Baby Tonight' was an important song to me, probably would have been my most important if I hadn't written 'Help Me Make It Through The Night,'" Kristofferson says.
In the name of important music, elsewhere in the interview, he highlights Sinead O'Connor. The interviewer says that Kris did right by sticking up for her and muses how I had the same experience. I was arguing with security people backstage. They were saying, 'By God, they don't do that in the USA. She can't come shit on this country.' I said, "Well, she's not shitting on anybody, she's talking about human rights; talking about child abuse," Kris says.
"I run into the same thing a lot on the road when I talk about stuff like that. The things that we have done in the name of democracy around the world. The US has overthrown something like 30 countries since the second World War. We've got stuff to answer for. It's not unpatriotic to question this. It's like I have seven children, but if they are messing up I'm going to point it out to them," Kris Kristofferson continues. "Sinead was standing up there looking like Joan of Arc, or something from the holocaust with her shaved head. She must have felt like what Blake said, "Do you think I'm wise?" The example of that should have shown some people that this is wrong."
