At that time, Rogers, who is known for his hits "Coward of the County," "Lady" and "She Believes in Me," performed a full set and even sang his signature tune, "The Gambler," with Phish.
A year later, the singer found himself performing at the Glastonbury Festival in England.
Those two engagements would seem incongruent to the traditionalist. Even Rogers didn't know what to think when his manager approached him with the dates.
"I said those are way out of my comfort zone," Rogers told The Park Record during telephone interview from his home in Atlanta, Georgia. "My manager said, 'You need to get out of your comfort zone.'"
On Saturday, Rogers will find himself in a venue that aligns with that zone when he performs with the Utah Symphony during the Deer Valley Music Festival at the Snow Park Amphitheater.
Since the concert comes a day after Independence Day, Rogers will sing a new patriotic song, "Merica," during the show.
"It's such a cool song and talks about the heart of this country," Rogers said. "At the end of the song, I have all the veterans stand up, and it's really touching." "Merica" is one of the singles off Rogers' most recent album, "You Can't Make Old Friends," that was released last fall.
The title track is a new duet Rogers did with his longtime friend and fellow Country Hall of Famer Dolly Parton.
This isn't the first time Rogers and Parton have joined forces.
"'[You Can't Make Old Friends]' is a wonderful piece of music," Rogers said. "The video show her and me over the years. I do the song in the show as well."
The album was released on Warner Bros., which was Rogers' label when he was with his band First Edition in the 1960s.
"When I went to the record company they told me not to worry about the radio and just cut 10 great songs," Rogers said of the new album. "That took so much pressure off of me as an artist."
Rogers could focus on selecting a variety of songs, including some he would never have listened to in the past.
One was a song called "Oh Baby, Don't Leave Me in the Nighttime" that is a duet with Cajun-music pioneer Buckwheat Zydeco.
"We're doing that with the symphony, so I'll be interested to hear how they play it," Rogers said.
In addition to the new songs, Rogers promised that he would perform 15 or 20 of his hits.
"I'll show a bunch of historic stuff on a screen and have fun with it," he said.
Even his classic songs have shown Rogers' knack for working with non-traditional county-music writers including Lionel Richie and the aforementioned Bee Gees.
"First of all you have to know that for the first 10 years of my music career I played upright bass in a jazz group," Rogers said. "From there I went to the New Christian Minstrels and sang the simplest kind of music, which was folk music."
While with the Minstrels, Rogers learned some valuable lessons that still resonate with his today.
"The '60s was all about social comment, and I learned that story songs that had social comment would make big impressions," he said.
That philosophy is reflected in his songs "Reuben James" and "Ruby, Don't Take Your Love to Town," which were both recorded and released in 1969, and "The Coward of the County," which reached No. 3 on the Hot 100 in 1980.
"Reuben James" is about an African American man who raised a white child. "Ruby" is about a Vietnam War vet who comes home and finds out his wife is having an affair, and "Coward of the County" is about a rape.
"I think those types of songs are my forte," Rogers said.
However, the singer has also struck gold with his ballads, including the No. 1 smash, "Lady," which was written and produced by Lionel Richie, just at the time he was leaving the Commodores.
"I tried to pick ballads that every man would like to say and what every woman would like to hear," he said. "When you look at that through the years with 'She Believes in Me,' 'You Decorated My Life' and 'Buy Me A Rose' all fall into that category."
One of those songs that will be missing from the Deer Valley concert is "Don't Fall In Love with a Dreamer," a duet Rogers sang with Kim Carnes that peaked at No. 4 in 1980.
"I can't do that one because Kim sings too high, but I love our voices on that song, because it sounds like we're hemorrhaging," Rogers said with a laugh. "I can sing it if she sings it with me, but I can't sing it by myself because of those high notes. I'll leave that up to the young boys."
Looking back on his 50-year career, Rogers is still amazed.
He has sold more than 165 million records worldwide, and has won three Grammy Awards, seven Academy of Country Music Awards, 13 American Music Awards and a Willie Nelson Lifetime Achievement Award from the Country Music Association, to name a few.
"It's been long and industrious, but it tends to run together," he said.
However, Rogers was able to gather his thoughts to write a memoir, "Luck or Something Like It" in 2012.
The book is about how luck plays such an important part of a career, he said.
"A lot of cool things happened and a lot of not-so-cool things happened," he confessed. "It wasn't hard to reveal things that happened in my life, because I'm a pretty open person and I found out a long time ago that if you hide something, it will be discovered. If you tell them, nobody cares."
Still, Rogers knows he has some faults.
"I say there's a fine line between being driven and being selfish and I think I crossed that line a few times when I was younger, but money didn't drive me — success did," he said. "I think I had something to prove to my mom and my dad and I was gone too long in some of the marriages. Anybody I hurt in the process, I truly feel sorry for, but, honestly, I wouldn't be where I am if I didn't make those decisions."
Rogers' latest writing venture is a novel with Mike Blakely called "What Are the Chances." It's a novel that does have some autobiographical references.
"It's about a singer who's trying to make it and gets sidetracked from time to time and falls in love with the wrong person," Rogers said. "It was a cool experience writing that book. They're talking about making it into a movie."
Although Rogers has acted, written books and produced, he still is a singer, but an older and wiser one.
"I spoke with George Burns before he passed and asked him how he kept working at 90 years old," Rogers remembered. "He said, 'Kenny, stay booked.'
"I realized what he was saying was you have to have commitments," Rogers said. "You have to have a reason for being somewhere. So, would I have ever thought to play those shows at Bonnaroo and Glastonbury? No. Am I glad I did? Yes."
At 75, Rogers' commitments are his 10-year-old twins.
"My boys give me a whole different sense of purpose, and I'm staying booked," he said. "I'm excited about the symphony. It will be great fun."
The Utah Symphony | Utah Opera's Deer Valley Music Festival will present Country Music Hall of Famer Kenny Rogers on Saturday, July 5, at 7:30 p.m. Tickets range from $42 to $80 and are available by visiting www.artix.org or www.deervalleymusicfestival.org.