He was no regular Joe. His first single, "Home," became the first debut ever to reach number One on Billboard, Radio & Records and Gavin charts.
But starting with 1993's "Honky Tonk Attitude," Diffie went for the funny bone ("Prop Me Be Up Beside the Jukebox (If I Die)," "John Deere Greene," "Third Rock From the Sun," " I"m in Love With a Capital 'U'" "Bigger Than the Beatles" and "Pickup Man"). While leaning toward novelty tunes, he leaned away from the more traditional sounds that first attracted him to the public.
Times have changed, and so has Diffie. Follow-up albums "Life's So Funny in 1995 and "Twice Upon a Time" in 1997, featuring more of the same fare, did not do so well.
With the June release of "A Night To Remember," the Oklahoman has gone back to what brought him to the show.
In a phone interview from his Nashville office, he says the decision was a conscious one.
"It was mine and my two new producers' (decision)," he says. "Basically, they asked me what I'd like to do. They were very open. We wanted to concentrate mostly on songs with substance to them and particularly those with love themes."
He says he had quite a bit of control in choosing material for the album.
"Obviously, I had to like the songs, or I wouldn't have recorded them," Diffie says. "I've never been forced to do a song, though I have been coerced. They asked me what I wanted to do."
Whether the album is the best of his career or not, Diffie, 40, says he wasn't sure, but that he liked it a great deal.
"It sure feels different," says the former demo singer of the album. "I'm gonna say it is (my favorite), along with my first album."
Studio musicians these days play on a different album almost daily. As a result, many albums by different artists sound similar. Diffie says his new release does not follow that trend.
"The pickers played outstanding," he says. "I've never done an album where all the pickers were as enthused. The whole album was based on not compromising in any aspect. These guys play on albums every day. With a little inspiration, they liked this one a lot."
So much so that Diffie says that given complete control, his albums would sound like this one, with a slight exception.
"It would probably be more stone country," he says.
He says that a more hard-core sound best represents him, that in another era he would have been one of the dyed-in-the-wool honky-tonkers. However, he says that he considers himself fortunate in that he can sing a number of styles, including more rock oriented material.
"The thing that I feel is pretty cool is that I can be pretty versatile," Diffie says, "and yet stay current. I feel I can do whichever (style)."
When pressed to choose, Diffie noted several favorites on the new album.
"If I had to pick one it would have to be 'Better Off Gone.' That one was real special," he says. "I really like the low register vocals (on it) a lot."
Another favorite, "You Can't Go Home," had been on Diffie's mind for some time. He says he wanted to record it for an earlier album, but his producer at the time didn't like it.
"I always gravitated toward that one," he says. "That song was about eight years old, so it sounded old, the demos did. Maybe that's why my previous producer didn't want it. I liked it because it was musically right in your face."
The song tells of a man whose gone back to the location of his childhood and past love, only to find that everything had changed. Diffie says that he personally related to that.
"I remember going back as an adult to a place where I sometimes stayed with my grandparents as a kid and seeing this barn they had and thinking that it always seemed so much bigger back then," he says. "You really can't go back home."
Some wish country would go back, back to the days when it was more country. As country moves, for some fans, perilously close to pop, Diffie says that he'd thought about it, but still isn't quite sure whether the genre has moved too far.
"In my tastes, yes we have (gone too far)," he says. "(However) I think it is a good thing in that a lot of listeners have come along with the popularity. To me, I feel like we have so many entertainers that we have gotten away from good songs. There are great songs out there. See, when I started there were like 80 artists signed to major labels. Now, it's about 300. And there are only so many songs.
"We're sellin' the sizzle right now," he says with a sigh.
And while more progressive artists such as Shania Twain and Garth Brooks garner much by way of awards, Diffie's contributions have not gone unnoticed.
Indeed, honors have been many for Diffie, including winning a Grammy earlier this year for his participation in the recording of "Same Old Train" with a slew of other artists. Still, his 1993 induction as a member of the Grand Ole Opry stands as a beaming highlight.
"That's one of the best parts of my career," he says of becoming an Opry member. "A thrill. It's such an elite group. I just couldn't believe it when I was invited to join."
Other things may be brewing for Diffie.
Before making it to Nashville, he played in a bluegrass band. Last year he appeared on Ralph Stanley's "Clinch Mountain Country" album, performing with the bluegrass legend and his band The Clinch Mountain Boys on "Another Night." He says one day he'd like to record a bluegrass album of his own.
"I'd do it in a heartbeat," he says. "We actually talked about it with our record label. I played bluegrass for four years. That's what I listen to around the house."
Perhaps one day artists will be saying the same thing about Diffie. Or maybe they already are or will with his new album's release.
"This one was most refreshing," he says.