Between 1990 and 1999, he had his greatest chart success recording for Universal Music Group Nashville's MCA and Decca branches, with a total of eight albums between those two labels.

For the next ten years, he began to record on small regional labels while he was the house band for local Beaumont nightclub Cutters.

[15] Contributing musicians to Too Cold at Home included Richard Bennett, David Briggs, Mark O'Connor, Hargus "Pig" Robbins, Matt Rollings, Brent Rowan, and Glenn Worf.

Alanna Nash of Entertainment Weekly praised Chesnutt's singing voice and honky-tonk style, but felt that the album had too many cover songs.

[17] In 1994, Too Cold at Home earned a platinum certification from the Recording Industry Association of America (RIAA) for U.S. shipments of one million copies.

[3] The album included many of the same session musicians as its predecessor, along with guest vocals from George Jones on "Talkin' to Hank", and both Alison Krauss and Vince Gill on "It's Not Over".

[19] Mansfield wrote of the album in AllMusic that "Weak material weighs down Chesnutt's third release, though he still sings them like the most romantic western swinger since George Strait."

He praised the title track for its string section, but criticized the uptempo material as being inferior to "Bubba Shot the Jukebox" and "Old Flames Have New Names".

[27] Nash felt that the album was "class-A honky-tonk, ballad, and Texas swing, delivered by a guy whose instincts are usually as sure as his pitch", but criticized the lyrics of the closing track "The Will".

[29] The album received a positive review from David Zimmerman of Gannett News Service, who praised the variety of traditional-leaning country sounds and Chesnutt's singing voice.

"[38] Chesnutt co-wrote the track "As the Honky Tonk Turns", which he said was inspired by his early days singing in honky-tonk bars and observing the crowds.

[29] Rick Mitchell in The Encyclopedia of Country Music described it as a "honky-tonk concept album" that "bucked the commercial trend toward throwaway novelty tunes and lightweight country-pop.

"[45] In late 1998, Chesnutt recorded a cover version of Aerosmith's "I Don't Want to Miss a Thing" at the suggestion of Wright, who had heard the song on his car radio.

[3] Chesnutt said that he decided to cover the song because he felt that, despite his chart successes, he "wasn't getting noticed" due to the weaker sales of his last two albums compared to his first three.

[3] Nash wrote of the album that the cover was "a bit of a jolt", but added that Chesnutt "goes on to find enough snappy rhythm tunes and scampering Western swing to keep the toes tapping.

[58] Maria Konicki Dinoia of AllMusic also showed favor toward the cover songs while comparing Chesnutt's voice to that of Merle Haggard.

[60] Billy Joe Walker Jr. produced the album, and contributing musicians included Aubrey Haynie, Brent Mason, and Dan Dugmore.

[1][65] Jimmy Ritchey was the album's producer,[66] and one of several contributing songwriters along with Chesnutt, Jerry Salley, Dean Miller, Jason Sellers, and Kevin Fowler.

[3] Erlewine said of the album that "Chesnutt not only sounds comfortable and relaxed, he's re-energized, both by the straight-ahead setting and the freedom to pick songs without an eye on the airwaves.

"[67] Robert Loy of Country Standard Time considered the disc a concept album, noting the unifying theme of alcohol consumption in most of the songs.

[1][69] Its title track was previously a pop hit for The Marshall Tucker Band, and many of the other songs on the album were covers as well, including Charley Pride's "A Shoulder to Cry On" and Hank Williams's "Lost Highway".

[70] Barry Gilbert of the St. Louis Post-Dispatch rated the album "B", praising Chesnutt's singing voice and the contrast of the title track with the other cover songs.

[70] Mark Deming of AllMusic stated that "while Heard It in a Love Song lacks the hard country feel of [Savin' the Honky Tonk], it's a solid set that confirms the man's musical instincts are back on track.

[3] The album once again featured Jimmy Ritchey as producer, with contributing musicians including Glenn Worf, Brent Mason, Eddie Bayers, and Lonnie Wilson.

[75] Thom Jurek referred to the album as "a no-frills, solid, lean, mean, rocking, emotionally sincere tribute to the outlaw generation, which is, in many ways, an extension of Chesnutt's own persona.

[6] Jack Hurst of the Chicago Tribune wrote that he was "a throwback to the inwardly-tough, just-do-it kind of country star they were making back when they minted George Jones, who preceded Chesnutt out of the rough-and-tumble East Texas honky-tonks 40 years ago.

[2] Mitchell also noted that Chesnutt was able to have success with both ballads and uptempo material such as "Bubba Shot the Jukebox" and "Old Flames Have New Names", as well as the strong presence of cover songs from the 1950s and 1960s.

[5] He also said that some of the tracks on Savin' the Honky Tonk were songs that the major labels had rejected, and that he would "rather sell 100,000 albums [of traditional country] than 6 million of some crap that I wasn't happy with.

[29] In late 1995, following Waylon Chesnutt's birth, Tracie typically stayed home at the couple's house in Jasper, Texas, while also working as an artist.

[89] On November 1, 2023, Chesnutt was hospitalized for an issue that required critical care, and underwent multiple tests to determine the exact problem.