But now at the ripe old age - for a musician anyway - of 45, Gill seems to be tackling not only the past, but also looking ahead to his own future in country with his new album "Next Big Thing."
The Oklahoman mixes it up stylistically between honky tonkers, ballads, a Spanish touch here, a Cajun bent there and lots of his usual powerful guitar work and tenor voice.
But from the get go of the title and lead-off track, Gill seems to be reflecting not only on his career in Music City, a career that has afforded him numerous awards and huge hits, but also the difficulty of staying at the top.
"For a little while you can do no wrong," sings Gill in the title track song he wrote with Al Anderson and John Hobbs, "Well live it up, son, 'cause it don't last long/There's always somebody waitin' in the wings/Thinkin' they're gonna be the next big thing."
While it would be easy to think that Gill is inward looking, Gill takes a different tack.
"'Next Big Thing' definitely has got a humorous element to it," says Gill in a telephone interview from Nashville. "It was meant to make you laugh. 'Get a bellybutton ring and lose weight.' (Gill has had his moments where he's been a lot heavier than he would have liked and recently dropped about 30 pounds.) It's making fun of myself. It 's just telling the truth because that's telling what happens. Our culture (says) 'the next big thing is this, and it's not that any more. It's this'. It changes and changes and changes. To be able to laugh about that is fun."
Gill also seems to be looking at his past on "Young Man's Town," a song he wrote by himself.
"You wake up one morning, and it's passed you by
You don't know when, and you don't know why
You feel like an old memory hangin' 'round
Man you gotta face it - it's a young man's town
You knew this day was comin' all along
So why bitch and moan and say they've done you wrong
Just teach 'em what you know, and pass it on down
'Cause man, you gotta face it - it's a young man's town"
Gill describes "Young Man's Town" as a "little more poignant. It's a little more about life. At some point, the next generation is going to come along and take your spot whether it be the music business, the insurance business...I've been cast aside. Now what do I do?"
"I used to hate to hear to hear people be bitter when the young one's come along and take that slot," says Gill. "You got to give them a chance if you want them to continue and pass it down."
"It's kind of coming grips with the truth," says Gill of the song.
Gill says that in thinking about recording "Next Big Thing," he wanted to change direction from his previous two efforts, "Let's Make Sure We Kiss Goodbye" from 2002 and "The Key" from 2000.
"I think my last two records, I enjoyed them, and I'm glad I made them, and I love what they did for me personally" says Gill. "I just felt like it was time to dust off my imagination as a songwriter. Bring some humor back. Cut loose on the guitar. Just kind of get it all over the map again to people would listen to and say it's Vince, but it's not Vince. I like being a bit of a chameleon."
"I think it was as a conscious effort on my part like with "The Key." That record was really traditional country music. It never wavered from that. It was a familiar feel to country music's past. I kind of longed to hear that as much as anything. I knew going in they're not playing tons of traditional country music these days. I went through the process of losing my father and all the traditional records we grew up on. It was a somewhat a personal record. It met with not a lot of desire to get played (on radio). I kind of let slide things a little more on the contemporary side with the next record. It was not the majority (of the music). The next record was kind of up and fun and (done by) a happy guy (who) fell in love and had songs about it. And it just didn't have the blues side to it that people like most about my record." '
Gill is referring to his marriage to Christian/pop singer Amy Grant after his divorce from his first wife, Janis and later had a child. The music is decidedly upbeat and not overly hard country.
"I'm a lot more at peace today than maybe at years' past. I felt like I could get my imagination back and write songs about all kinds of things."
Another change is that Gill self-produced mainly because long-time producer Tony Brown left his perch as head of MCA to start his own label.
While Gill tackles different musical styles on "Next Big Thing," it's clear he has a love for country music's past.
That perhaps is never as evident as "Real Mean Bottle," a tribute to Merle Haggard, who penned the classic "Tonight the Bottle Let Me Down."
"I was having a conversation with Harold Bradley, who's probably the most recorded guitarist in history," says Gill. "He's done a session with Hank Williams Sr. They did this one song, and he went up to Hank after, and he said, 'that may have been the saddest song I've ever heard.' He said, 'that was a real mean bottle that wrote that song.'"