But, at 68, Kenny Rogers is not resting on his laurels. His latest album, "Water and Bridges," was a surprise hit. This fall, he's got another on the way — a career retrospective called "The Journey."
CBS News correspondent Russ Mitchell asks him what music fans are getting when they buy a Kenny Rogers album.
"I think you're buying where I am at my life at this time," Rogers says.
Where Kenny Rogers is, these days, when he's not on the road, is home in Atlanta, Ga., with his 2-year-old twins Jordan and Justin, and Wanda, his fifth wife, who happens to be an identical twin herself.
"When we first met, we decided we didn't want kids," Rogers says. "And then somewhere along the way — it was more than we bargained for."
Wanda was a 26-year-old college student working as a hostess in a restaurant when they met 15 years ago.
"I was on a date at the time," Rogers says. "Tacky, isn't it?"
Kenny liked Wanda's smile, he said, and asked the manager to give her his phone number. She thought it was a joke.
"I threw it in the trash," Wanda says. "And when they all dove after it, I knew, well, maybe it's not a joke."
It was no joke, in spite of their obvious age difference, and Kenny Rogers is the first to see the humor in that.
"The first date we went on, she had this little black dress with a big yellow bow on it," Rogers says. "I swear to God, she looked like she was 19-years-old. And I said, 'Look, let's make a deal. You dress a little older, I'll dress a little younger, and we'll meet somewhere in here. We can do this.'"
It's that good-natured honesty, combined with optimism, and hard work that's worked for Kenny Rogers ever since he was a kid. He grew up in Houston, the fourth of eight kids.
Rogers says his childhood was "great."
"You know, when you're poor and you have a bunch of kids in your family, you don't know that everybody's not poor. I had holes in my jeans well before it was fashionable. We lived in the poorest part of town, went to school in the richest part of town, but I didn't even know until I was in the sixth grade that there was a difference."
When he did notice, he set out to do something about it, earning $900 a week with the Bobby Doyle jazz trio when he was just 19-years-old. The only requirement, Doyle told him: he'd have to learn to play bass.
"I said, well, I already play guitar, and he said, yeah, but there's more demand for bad bass players than bad guitar players."
Next was a gig with the New Christy Minstrels and a chance to tour nationally.
"I went from avant-garde jazz to singing 'Green, green it's green, they say,' and I thought, 'Well, how mundane is that? But after I'd been at it a few months, I got it — now I was doing a show. Now I was making people laugh."
In 1968, Rogers and a few band members decided to form their own group, playing rock, instead of folk. They called themselves The First Edition. Success was instantaneous.
Mitchell recalls watching them on the Ed Sullivan Show.
"You know, Sullivan, for me, that was an epiphany," Rogers says. "I remember vividly a light bulb going off and saying, 'Wow, I've really done something with my life.' "