He also co-wrote singles for Holly Dunn, Tim McGraw, and Jo Dee Messina, and recorded with Mary Chapin Carpenter, George Jones, and Marty Stuart.

[8] Montgomery, who was then the vice president of A&R at Epic Records, said that he wanted to sign Diffie to a contract with the label, but had to put the singer on hold for a year.

[2] The label released Diffie's debut album, A Thousand Winding Roads, at the end of 1990,[3] with Montgomery and Johnny Slate as producers.

[14] In 1991, Diffie co-wrote the tracks "Livin' on What's Left of Your Love" and "Memory Lane" on labelmate Keith Palmer's debut album.

[15] Diffie's second album, titled Regular Joe, was released in 1992 and was certified gold by the Recording Industry Association of America.

Brian Mansfield gave the album a positive review in Allmusic, saying that it "has all the clichés of country music, and all the good stuff, too.

"[19] Richmond Times-Dispatch reviewer Norman Rowe referred to Diffie as a "pleasant surprise" and called "Is It Cold in Here" "the sort of tear-jerker George Jones has worked wonders with in the past".

[25] Tim McGraw also included two of Diffie's songs on his 1993 debut album: another version of "Memory Lane", which he released as a single, and "Tears in the Rain".

Thom Owens wrote that he began "adding more rock flourishes" on this album,[31] and Nash said that Diffie "not only understands the blue-collar ethic from the inside out – he's also familiar with its humorous underbelly.

The album's other two singles were "C-O-U-N-T-R-Y" and "Whole Lotta Gone" (previously the B-side of "Bigger Than the Beatles"), both of which peaked at 23 on the country music charts in 1996.

[2] Country Standard Time critic George Hauenstein praised the album for containing "songs that are slightly different from [what] those other artists sing.

[36] Nash gave "Bigger Than the Beatles" a C-minus rating, calling it "just a lame device to evoke the names of beloved rock heroes.

Doug Virden and Drew Womack, who then recorded on Epic in the band Sons of the Desert, sang backing vocals on it.

[2] Country Standard Time gave the album a positive review for having "nary a novelty tune in the bunch",[44] and Nash wrote that it had a "surprising depth of feeling.

Regarding this album, Diffie told Billboard that its material had a common theme of love, and that he wanted to create a more contemporary sound through the production.

Only one other single was released from the album: "This Pretender" (co-written by Rascal Flatts lead singer Gary LeVox), which failed to make the country music Top 40.

Country Weekly reviewer wrote that Diffie "deals with adult emotions" and described the title track as "a shimmering ballad perfect for his expressive tenor.

[51] Tougher Than Nails produced a top-20 hit in its title track, followed by "If I Could Only Bring You Back", which peaked at number 50 and spent only eight weeks on the charts.

"[53] In 2005, Jo Dee Messina released "My Give a Damn's Busted", which Diffie co-wrote and originally recorded on In Another World.

[54] After leaving Broken Bow, Diffie continued to tour, primarily playing smaller venues and county fairs.

[60] He co-produced the album with Luke Wooten, and included on it the song "Tennessee Tea", which Diffie originally recorded while he was in Special Edition.

[62] Later in the year, Diffie collaborated with Aaron Tippin and Sammy Kershaw on the album All in the Same Boat, and cut the single "Girl Riding Shotgun" with D Thrash of the Jawga Boyz.

[1] In 2023, Hardy paid tribute to Diffie during the Academy of Country Music ceremony, where he joined Morgan Wallen and Post Malone in live renditions of "Pickup Man" and "John Deere Green".

[63] Steve Huey of Allmusic wrote that Diffie "lent his traditional sensibilities to humorous, rock-tinged novelties and plaintive ballads.

"[3] His early albums for Epic mostly consisted of ballads, but starting with Honky Tonk Attitude, he began to include more up-tempo and novelty numbers.

[3] Starting with A Night to Remember, Diffie returned to a more ballad-oriented sound; Mike Kraski, then the senior vice president of sales for Sony Music Nashville, thought that the albums before it had over-emphasized his novelty releases.

[43] Diffie's influence on music was recognized with his name being mentioned in the 2019 hit song Raised on Country by artist Chris Young.

[45] William Ruhlmann wrote that Diffie "has put together a decade-plus career in country largely on his ability to succeed" in "scour[ing] Nashville publishers for 10 good compositions in the established style", and that he was an "adequate but undistinguished singer.

From 1992 to the early 2000s, Diffie held a charity concert and golf tournament benefiting First Steps, a nonprofit organization for the education of mentally and physically impaired children.

[1][73] ^[A] Nominated alongside Mary Chapin Carpenter^[B] Nominated alongside Clint Black, Merle Haggard, Emmylou Harris, Alison Krauss, Patty Loveless, Earl Scruggs, Ricky Skaggs, Marty Stuart, Pam Tillis, Randy Travis, Travis Tritt and Dwight Yoakam^[C] George Jones' "Friends" also includes: Vince Gill, Garth Brooks, Travis Tritt, Mark Chesnutt, Alan Jackson, Pam Tillis, T. Graham Brown, Patty Loveless and Clint Black^[D] Nominated alongside George Jones and Friends