But the Georgian hasn't enjoyed the same success since.
That may not necessarily change with his new CD, "That's Why I Sing This Way," on Audium. The dozen-song project contains all covers save the title track with some familiar songs and some foreign to current day listeners.
The disc also includes some familiar names like Yoakam, Haggard, Paycheck and Jones helping out.
But at least Singletary's doing exactly what he wants.
"I'm real excited about this record," he says in a telephone interview from Nashville. "This is my fifth project, so I've waited five projects to do something like this. I wanted to do it from the day I moved to Nashville, but I have not been able to."
After three albums on Giant, Singletary, 31, indicates he has met his match with Audium, the independent record label also home to folks like Loretta Lynn and Dale Watson.
"I got hooked up with a record company that was real excited about country music and has the passion about it that I have. So, it makes it a lot easier to record music like this and have a record company behind you and stick their neck out as much I want to stick my neck out."
"This is what I moved to Nashville to do," says Singletary. "I moved to Nashville to be a traditional country singer. I listened to folks like Geroge Jones and Merle Haggard, and I was wanting to do the music they were doing and fell in love with, and that brought me to town."
While Singletary always has maintained a traditional music bent and sings with a drawl, that style has not exactly been overwhelmingly popular in Nashville in the past few years.
Instead, country has become increasingly homogenized with many songs having far more of a pop or rock feel than the pure country sound on Singletary's latest.
And the record industry itself changed. For example, Giant, Singletary's old label, is no longer around, having been absorbed by Warner. An increasing number of indie labels sprouted up in the past two or three years.
"The business has changed considerably since I moved to town from when I had my first record out," says Singletary, whose first single was "I'm Living Up to Her Low Expectations."
"We didn't do this record to be on the soap box or anything," he says. "We did this record from the heart, and it's more of me than anything I've ever done before. I found people and I'm working with people that believe in it and are as passionate about this music as I am."
The disc includes such familiar songs as Buck Owens' "Love's Gonna Live Here Again" with backing help from Dwight Yoakam, "Walk Through This World With Me," a hit for George Jones in 1967 with Jones singing back up, "I'd Love to Lay You Down," a hit for Conway Twitty in 1980, "Long Black Veil" and Merle Haggard's "Make Up and Faded Blue Jeans" with The Hag providing backing vocals on his song from 1980.
Why an album mainly of covers instead of just singing straight ahead, newly-penned traditional country songs?
"In today's radio, the people that are listening to radio today are a generaton that have have never heard these songs," says Singletary. "There are a lot of (radio) programmers that have never heard these songs today unfortunately. There are a lot of them out there who do know their songs. A lot of them played these songs when they were hits for the artists that played them originally. And there are a lot out there that these are brand new records for them."
"We don't want to do it as an influence album, duets album (the guest singers tend to provide backing vocals instead of being outfront)," says Singletary. "We want to do it just as great country songs."
Singletary says he was interested in recording songs "you don't hear in every bar you've gone into, but if you asked the band, they would definitely know them."
The process of song selection was not hard, according to Singletary. "We kind of sat down one day and made a list of 50 to 100 songs that we might want to do. I had some that I knew I wanted to record ("I Never Go Around Mirrors," a song recorded by Keith Whitley. "I've been a huge Keith Whitley for a long time)."
"We didn't want to get too ballad heavy," says Singletary, explaining the process for covering "Love's Gonna Live Here." "I love country ballads. I'm definitely a Buck Owens fan myself. I listened to Buck Owens, but I remember Buck Owens as the guy on Hee Haw who wore overalls. He definitely deserves (credit) as a great stylist in this business. When we talked about needing to find some uptempo stuff, we thought about 'Tiger by the Tail,' but 'Love's' just jumped in our lap."
Yoakam assumes the Don Rich role - Owen's late sidekick - in doing harmonies. Singletary did not know Yoakam, but record label head Nick Hunter did from his days at Warner, Yoakam's former label.