1990–1991: A Thousand Winding Roads The label released Diffie's debut album,
A Thousand Winding Roads, at the end of 1990, Its first single, "
Home", reached the top of the
Billboard Hot Country Songs chart. The song also reached number one on the country music charts published by
Radio & Records and
Gavin Report, making him the first country music artist to have a number-one debut single on all three charts, as well as the first country music artist to have a debut single spend more than one week in the number-one position at the latter two publications. Diffie co-wrote the album's second and fourth releases, "
If You Want Me To" and "
New Way (To Light Up an Old Flame)"; Between these two songs, "
If the Devil Danced (In Empty Pockets)" became Diffie's second
Billboard number one. Diffie also performed his first concerts in late 1990, touring with
George Strait and
Steve Wariner. 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.
1992: Regular Joe Diffie's second album, titled
Regular Joe, was released in 1992 and was certified gold by the
Recording Industry Association of America. The first two singles from the album both peaked at number five on
Billboard: "
Is It Cold in Here" and "
Ships That Don't Come In", Both of these songs made the country top 20, respectively reaching 16 and 15, and the duet was nominated for a
Grammy Award for Best Country Collaboration with Vocals at the 35th Grammy Awards in 1993. The final single from
Regular Joe was "Startin' Over Blues" (originally the
B-side to "Ships That Don't Come In"), which peaked at number 41.
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".
Alanna Nash of
Entertainment Weekly thought that Diffie "[sang] in his natural voice", but thought that its material "punches all the predictable thematic buttons." Also in 1992, Diffie was nominated by the
Academy of Country Music for Top New Male Vocalist, along with
Billy Dean and
Mark Chesnutt, but lost to Billy.
1993: Honky Tonk Attitude Honky Tonk Attitude (1993) shipped a million copies in the United States and was certified platinum. Nash rated the album more favorably than the ones before it, saying that Diffie "is maturing into a first-rate interpreter of working-class woes." Also in 1993, Diffie was inducted into the
Grand Ole Opry. Several other artists and he won that year's
Country Music Association award for Vocal Event of the Year, for their guest vocals on George Jones's "
I Don't Need Your Rockin' Chair". 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".
1994–1996: Third Rock from the Sun, Mr. Christmas, and ''Life's So Funny'' Third Rock from the Sun was Diffie's highest-charting top country album (where it reached number six The album included two consecutive number-one singles in its
title track and in "
Pickup Man". The latter of those two songs was Diffie's longest-lasting number one, at four weeks. Both songs also entered the hot 100, respectively peaking at 84 and 60. The album's next single, "
So Help Me Girl", peaked at number two on the country charts and 84 on the pop charts, in addition to topping the
RPM country charts. The song was covered in 1997 by English singer
Gary Barlow. Diffie followed the song with
"I'm in Love with a Capital 'U and "
That Road Not Taken", which respectively reached country peaks of 21 and 40. and Nash said that Diffie "not only understands the blue-collar ethic from the inside out – he's also familiar with its humorous underbelly." In mid-1995, he recorded the title track for
Columbia Records's ''Runnin' Wide Open
, an album comprising NASCAR-themed songs by various artists. He issued two albums later in the year. The first was a Christmas project titled Mr. Christmas'', which comprised covers of traditional Christmas songs, as well as newly written songs. One of these original songs, "LeRoy the Redneck Reindeer", was issued as a Christmas single late in the year, peaking at number 33 upon its initial release and re-entering the country music charts for the next two years based on Christmas airplay. His other release that year was the studio album ''
Life's So Funny''. It was led off by "
Bigger Than the Beatles", the last number-one single of his career. 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.
Country Standard Time critic George Hauenstein praised the album for containing "songs that are slightly different from [what] those other artists sing." Owens thought that it was a "varied collection of ballads and midtempo rockers", but said that it was not "as consistently engaging" as
Third Rock from the Sun. Nash gave "Bigger Than the Beatles" a C-minus rating, calling it "just a lame device to evoke the names of beloved rock heroes."
1997–1998: Twice Upon a Time and Greatest Hits Twice Upon a Time followed in 1997. Its singles all failed to make the top 10 on the country charts, with lead-off "
This Is Your Brain" reaching number 25, followed by "
Somethin' Like This" at number 40 and "The Promised Land" at number 61, the lowest-peaking single of his career. Also included on the album was "I Got a Feelin'", which
Tracy Lawrence previously recorded on his 1994 album
I See It Now. Jeffrey B. Remz criticized the two novelty songs on
Twice Upon a Time for lacking substance, and thought that most of the ballads were well-sung, but that the production "lacks any soul." Owens said that it "doesn't offer anything new or especially remarkable from Joe Diffie." In mid-1998, Epic Records released Diffie's
Greatest Hits package, which featured three new cuts. Among these were "
Texas Size Heartache", and its B-side, "Poor Me", which respectively reached numbers four and 43 on the country charts. At the end of the year, Diffie recorded a cover of
Charlie Rich's "
Behind Closed Doors" for the multiple-artist album
A Tribute to Tradition on Columbia Records. Diffie's version of the song peaked at number 64 based on unsolicited airplay.
1999–2000: A Night to Remember His final album for Epic Records, titled
A Night to Remember, was released in 1999. As he did with the new cuts for his
Greatest Hits package, Diffie worked with producers
Don Cook and
Lonnie Wilson, a friend of Diffie's who worked primarily as a session drummer and songwriter, and formerly fronted the band
Bandana. Its
title track spent 29 weeks on the country charts and peaked at number six; it was his only top 40 on the hot 100, where it reached number 38. and Nash wrote that it had a "surprising depth of feeling."
2001–2004: In Another World and Tougher Than Nails In 2001, Sony Nashville transferred Diffie from its Epic division to the
Monument Records division due to a corporate decision that Epic had too many artists and Monument had too few. Cook and Wilson also produced his only album for Monument, which was titled
In Another World. 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. William Ruhlmann called the album "sturdy formula country", After Monument closed its Nashville branch, Diffie began touring with
Mark Chesnutt and
Tracy Lawrence on the Rockin' Roadhouse Tour, which began in 2002.
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. This latter song was also his last charting single. and
Country Standard Time said that the album "shows that he's still got the talent that took him to stardom in the first place." In 2005, Jo Dee Messina released "
My Give a Damn's Busted", which Diffie co-wrote and originally recorded on
In Another World. Her version of the song, included on her album
Delicious Surprise, was a number-one single that year.
2004–2020: The Ultimate Collection and later activity After leaving Broken Bow, Diffie continued to tour, primarily playing smaller venues and
county fairs. In 2007, he joined with
Lonestar,
Charlie Daniels, and
Craig Morgan to perform a benefit concert for Sgt. Kevin Downs, a soldier who was severely wounded in
Iraq. In 2008, Diffie compiled and released a live album, and he signed to
Rounder Records later in that year. Rounder released an album called
The Ultimate Collection, which comprised re-recordings of his hits for Epic. His next project for Rounder,
Homecoming: The Bluegrass Album, was released on October 26, 2010. It includes collaborations with
The Grascals,
Rhonda Vincent, and other bluegrass artists. Diffie toured at various county fairs in August 2010 in support of it. 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. Allmusic reviewer j. poet gave this album a positive review for showing Diffie's bluegrass influences. 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. This was followed in 2019 by a vinyl album called
Joe, Joe, Joe Diffie. ==Musical styles==