Kris Kristofferson (pictured) passed away in Maui on Sept. 28 at the age of 88.

When Bob Dylan was honored in 2015 as the MusiCares Person of The Year ceremony in Los Angeles, he paid tribute to fellow music icon Kris Kristofferson.

Kris Kristofferson (left), Marty Dread (center) & Pat Simmons (right) backstage at the MACC. Courtesy photo

Setting a new standard in Nashville, his longtime friend Willie Nelson once declared how Kristofferson, “brought us out of the dark ages.”

His family released a statement. “It is with a heavy heart that we share the news our husband/father/grandfather, Kris Kristofferson, passed away peacefully on Saturday, Sept. 28 at home. We’re all so blessed for our time with him. Thank you for loving him all these many years, and when you see a rainbow, know he’s smiling down at us all.”

Kristofferson retreated to the idyllic seclusion of Hana in 1990. “Part of the reason I came here to live was the sense of family out here,” he explained in the documentary “One Man, One Voice” by Maui filmmaker Kenneth Martinez Burgmaier. “We became part of the community. It reminds me of where I grew up in Brownsville, Texas. It’s like coming home. I love it here.”

He once told Maui musician friend Marty Dread that he had moved to Hana to escape the world’s madness. “I asked him once, of all the places he could have settled down, why Hana?” Marty recalled. “He wanted to separate himself and raise his kids from what he called the madness of the world.”

A three-time Grammy winner, over the years, his songs were recorded by a remarkable array of artists from Waylon Jennings, Bob Dylan and Frank Sinatra, to Elvis Presley, Janis Joplin and the Grateful Dead. By 1987, it was estimated that more than 450 artists had recorded his compositions.

Kristofferson’s self-titled debut album in 1970, was filled with timeless songs, many of which were hits for other artists. He took home the Grammy for Country Song of the Year for “Help Me Make It Through the Night” in 1971. Then, when Janis Joplin recorded his iconic song “Me and Bobby McGee,”his popularity was sealed.

By the time of his top-charting 1973 album “Jesus was a Capricorn,” even Frank Sinatra and Elvis Presley were recording his songs.

After his success in the early-1970s, he met singer Rita Coolidge. Their first duo album, “Full Moon,”topped the country charts, sold gold, and won a Grammy Award. Coolidge remembered having fun singing at Lahaina clubs and visiting Hana, where they purchased land. “We bought the land together,”she explained. “When we divorced, we divided it, and whoever was going to build a house there, the other person would agree to sell.”

He was later a member of country music’s “Mount Rushmore,” The Highwaymen supergroup featuring Johnny Cash, Willie Nelson, Waylon Jennings and Kristofferson. Between 1985 and 1995, the group recorded three albums and a number one single, “Highwayman.”

In 2014, Kristofferson received a Grammy Lifetime Achievement Award. At the ceremony he was joined by Willie Nelson, Merle Haggard, and Blake Shelton. “It’s so much of a pleasure to be with these guys,”Kristofferson reported. “One of the best parts of my life has been the guys who are my real heroes are my closest friends. Willie is the closest friend I have.”

Released around his 80th birthday, Kristofferson’s most recent album, “The Cedar Creek Sessions,” was nominated for a Grammy for best Americana album. It featured live in the studio re-recordings of his best known and less familiar songs.

In recent years he collaborated on recordings with Joni Mitchell, British musician Moby, Sheryl Crow and Roseanne Cash.

In 1999, “60 Minutes” filmed Kristofferson driving a lawnmower around his Hana property. He referred to his home as “an old samurai poet warrior’s house,” where “I’m his groundskeeper.”

Along with supporting his Hana community, Kristofferson enjoyed helping our island musicians. Marty Dread recalled first meeting him in 1993. “My band did a series of concerts after Hurricane Iniki, and both Kris Kristofferson and Willie Nelson were on the Maui show. Kris approached me after our set and said, ‘Willie and I were talking, and we realized your band is speaking to your generation like we were.’ We were talking about geothermal protests and overdevelopment, and social issues. He said, ‘if I can help in any way musically, let me know.’ We spent a day together in the studio and came up with the song ‘Reggae Blues.’ He played harmonica and sang harmony.”

When Maui musician Lily Meola compiled songs for her critically acclaimed debut album “They Say,”she covered “Me and Bobby McGee,” joined by the veteran composer. “It was incredible; he was so sweet,” said Meola about the opportunity to record with him.

A couple of years later at the “Sing Out For Sight” benefit concert at the MACC, he teamed with Joan Baez to sing “Me and Bobby McGee.”

The music legend was among the many stars who helped his buddy Willie Nelson celebrate his 90th birthday with two concerts at the Hollywood Bowl in April 2023. Lukas Nelson recalled his favorite moment of the historic event was hearing “Nora Jones and Kris Kristofferson doing ‘Help Me Make It Through the Night.’”

Lukas Nelson posted a tribute on Facebook: “Kris helped me to believe in myself as a songwriter when I was a boy. Other than my father, he was my greatest inspiration. He embodied humility and kindness, and carried his grace into his words and music with unique eloquence. He was a great among greats. One of the coolest men in music.”

When the film of the celebration, “Long Story Short: Willie Nelson 90,” received its world premiere at the MACC, Kristofferson sat at the side of the stage with his wife Lisa, and watched for the entire screening.