That same year he was the Country Music Association's Male Vocalist of the Year and Horizon Award winner, and in 1985 he won the most coveted award in country music, the CMA Entertainer of the Year.
But soon after that, the well of success began to dry up.
"We really had a great run," Skaggs says, "but you know, new artists came out - Randy Travis and Ricky Van Shelton, people like that - and so after you've had six or seven years of a lot of success, people are kind of ready for a new sound, a new look, and that kind of thing. So we had a pretty tough time from '87, '88, on up through the early Nineties."
After enjoying 10 number one hits in a four-year span, Skaggs has only had two top-10 singles in the past decade. It's certainly not for lack of effort - he's released one good album after another without getting the attention he received earlier in his career.
"'My Father's Son' was my last record for CBS, for Sony, and that was such a good record. I mean, 'Same Old Love' was, man, what a great song, and that really, I think, had a chance. I mean, Tony Brown even told me - here's a man from another record label - he said, 'Man, it's a sin that that song didn't go number one.'"
Another negative was a backlash against Skaggs for bringing his Christianity to the fore, a move apparently turning off some in the industry.
After CBS let him go, he released two unsuccessful albums on Atlantic, including the aforementioned "Life Is a Journey," which came out in late July and Skaggs describes as "the big one that got away, ... one of the best records I've ever done."
"And then it just kind of got to the point where I said, 'Look, there's no way in the world I'll ever be able to figure out country radio.' You've got to do what you do. You can't let success or failure, either one, dictate what you do."
"I believe God made snowflakes different, and every snowflake is different, according to scientists, you know - so to me people are made different, too, and everybody has their own place in this world to add their ingredients, add their special little touch. So I felt like, 'Why would I want to be like somebody else?'"
So what has Skaggs done? He's started his own record label, Skaggs Family Records, and released a fabulous album, "Bluegrass Rules."
And as he talks about it over the phone, one can almost see the twinkle in his eyes and the glow in his face - that's how thrilled he sounds to be able to do the music he loves.
"Getting the freedom to do this record is like a man coming out of jail and having his first meal or something like that out in the free world, so I'm really, really excited about it. It's just so much fun to stand up on stage and play this music again. But being able to play it with such great musicians that I have right now in this band, Kentucky Thunder - these guys are so great, and they have such a respect of music of the past, but they know that we're standing in the present and putting our toe toward the next millenium, taking this music there. It's like a mission for us almost."
"When you don't have freedom to play music that you really love, then I think the fans know it, and certainly the listeners out there, when they see it on your face, they know you're not digging it. Nobody's that good of an actor...I think that's why people are getting so infected with this 'Bluegrass Rules' record. It's because when they see us live, they get infected. It is total smiles, it is total fun, and everybody is just so fired up and so excited about this music, especially the band, that it's infectious. People just say, 'Man, I've never heard bluegrass music before until tonight, and this is really great.' So we're getting a lot of great reviews on it. It just couldn't be better right now."
And just like he was doing 20 years ago, Skaggs is still trying to bring visibility and popularity to bluegrass music in a rock-and-country world.
"We're real excited about the future of it, and I just think that - I've said this for a long time, even before we started playing the music full-time - I really think bluegrass is going to be bigger in the next millenium than it ever was back in the Forties and Fifties when it was in its real heyday."
In a sense, Skaggs has come full circle: from an anonymous picker and singer in several seminal bluegrass bands in the Seventies, to one of country's megastars of the Eighties, back to a relatively obscure bluegrass bandleader in the Nineties.
Unfortunately, Skaggs probably won't be the one to save country music in the Nineties from its current poppish quagmire. It's going to take someone new, someone younger, someone like the baby-faced kid who took the country world by storm in 1981 with his fresh fusion of country and bluegrass instruments and those gorgeous high harmonies. Will the next Ricky Skaggs please stand up?