Kris Kristofferson comforts Sinéad O'Connor on stage at Madison Square Garden as she faced booing from the crowd.YouTube

Kris Kristofferson, the Grammy Award winning US country singer, passed away on Saturday, September 28 at his home in Malibu, California. He was 88 years old.

Kristofferson is being remembered for his decades-spanning, award-winning career in the wake of his death - though one of his most notable moments occurred in 1992 when he came to Irish singer Sinéad O'Connor's defense while on stage at Madison Square Garden. 

On October 16, 1992, two weeks after she tore up a picture of the Pope on “Saturday Night Live" as a form of protest against the Catholic Church, O’Connor was introduced by Kristofferson on stage at the iconic NYC venue during Bob Dylan’s 30th-anniversary concert.

“I’m real proud to introduce this next artist,” Kristofferson told the audience. “Her name has become synonymous with courage and integrity.”

Despite Kristofferson's warm intro, 25-year-old O'Connor was met with boos - fallout from her "SNL" stunt - which forced her to pause as she approached the microphone. Kristofferson came on stage and gave her an encouraging embrace.

When the piano player started Dylan’s gospel classic “I Believe in You," the boos only grew louder, prompting O'Connor to wave to cut the music.

She then emphatically launched into an acapella performance of Bob Marley's "War," the same song she sang on "SNL" when she tore up a picture of Pope John Paul II in a sharp criticism of the Catholic Church.

When the song was done, O'Connor offered a defiant look to the audience. She turned to exit the stage and appeared to break down crying, but Kristofferson was there again to embrace her.

O'Connor's impact on Kristofferson was profound, leading him to pen the song "Sister Sinead," which was included on his 2009 acoustic album "Closer to the Bone."

In his song, he sings: “It's askin' for trouble to stick out your neck / In terms of a target a big silhouette / But some candles flicker and some candles fade/ And some burn as true as my sister Sinéad.”

In 2010, Kristofferson recounted the Madison Square Garden incident during an appearance on RTÉ One's "Saturday Night with Miriam."

"Well, it was Bob Dylan's birthday, I can't remember what birthday," Kristofferson told host Miriam O'Callaghan.

“They were celebrating it at Madison Square Garden, I think.

"And Sinéad had just recently on ‘Saturday Night Live’ torn up a picture of The Pope in a gesture that I thought [was] very misunderstood. 

“And she came out and got booed.”

He continued: "I went out. They told me to get her off the stage and I said, 'I'm not about to do [that]. 

“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."

Later during the episode, O'Connor joined Kristofferson for a duet of his Grammy Award-winning song "Help Me Make It Through the Night."

However, in January 2019, O'Connor had some choice words about Kristofferson on Twitter in response to a now-viral thread posted by writer Audra Williams.

In her thread about the infamous night at Madison Square Garden, Williams shared a photo of Kristofferson and O'Connor on stage, writing "The recent Gillette ad has started/furthered a lot of conversations about what alternatives to toxic masculinity look like. This is it."

O'Connor, who died in July 2023, didn't agree. Replying from her @magdadavitt77 handle, the Irish songstress wrote in since-deleted posts: “I would not agree Kris wasn’t toxically masculine.

"He took full advantage when he got the chance and then immediately turned nasty once...”

She added the hashtag #NoHeroOfMine.

She later elaborated: “In case my use of the words ‘took advantage’ [in] an earlier tweet might be misconstrued I wish to make clear that in no way, shape or form was I in any way sexually assaulted by Kris Kristofferson. And that the one time we did have sex, it was consensual.”