[7] Tritt began writing music while he was attending Sprayberry High School; his first song composition, entitled "Spend a Little Time", was written about a girlfriend whom he had broken up with.

[9] He also founded a bluegrass group with some of his friends and won second place in a local tournament for playing "Mammas Don't Let Your Babies Grow Up to Be Cowboys".

Recorded in late 1988 and released on August 7, 1989,[17] the song spent 26 weeks on the Hot Country Singles & Tracks charts, peaking at number nine.

[18] Country Club was certified platinum by the Recording Industry Association of America (RIAA) in July 1991 for shipments of one million copies, and no medals since in 1996.

[23] Brian Mansfield of AllMusic gave the album a positive review, saying that "Put Some Drive in Your Country" paid homage to Tritt's influences, but that the other singles were more radio-friendly.

[24] Giving the album a B-minus, Alanna Nash of Entertainment Weekly compared Tritt's music to that of Hank Williams, Jr. and Joe Stampley.

"Here's a Quarter (Call Someone Who Cares)" and the Marty Stuart duet "The Whiskey Ain't Workin'", respectively the first and third singles, both reached number two, with the number-one "Anymore" in between.

[14] "Bible Belt", another cut from the album (recorded in collaboration with Little Feat), appeared in the 1992 film My Cousin Vinny (the lyrics for the song, however, were changed for the version played in the movie to match the story line).

This song, which featured backing vocals from Brooks & Dunn, T. Graham Brown, George Jones, Little Texas, Dana McVicker (who also sang backup on Tritt's first two albums), Tanya Tucker and Porter Wagoner on the final chorus, peaked at number five.

[21] Stephen Thomas Erlewine of AllMusic thought that T-R-O-U-B-L-E followed too closely the formula of It's All About to Change, but said that the songs showed Tritt's personality.

[18] The album included two co-writes with Gary Rossington of Lynyrd Skynyrd, and guest vocals from Waylon Jennings and Hank Williams, Jr. on the cut "Outlaws Like Us".

[21] AllMusic reviewer Brian Mansfield said that Tritt was "most comfortable with his Southern rock/outlaw mantle" on it, comparing "Foolish Pride" favorably to "Anymore" and the work of Bob Seger.

[40] Alanna Nash praised the title track and "Tell Me I Was Dreaming" in her review for Entertainment Weekly, but thought that the other songs were still too similar in sound to his previous works.

[39] 1995's Greatest Hits: From the Beginning included most of his singles to that point, as well as two new cuts: the Steve Earle composition "Sometimes She Forgets" and a cover of the pop standard "Only You (And You Alone)".

The song won both artists that year's Country Music Association award for Vocal Event, Tritt's third win in this category.

The album accounted for one more top ten hit, a cover of Waylon Jennings's "Where Corn Don't Grow", which Tritt took to number six in late 1996.

"She's Going Home with Me" and "Still in Love with You" (previously the respective B-sides to "Where Corn Don't Grow" and "More Than You'll Ever Know") were the third and fifth releases, peaking at 24 and 23 on Hot Country Singles & Tracks.

[45] He also performed on Frank Wildhorn's concept album of the musical The Civil War, singing the song "The Day the Sun Stood Still".

[18] Michael Peterson (who recorded for Warner Bros.' Reprise label at the time) co-wrote and sang backing vocals on the title track,[47] which went to number 38 country in early 1999.

[18] Late in 1999, Tritt recorded a cover of Hank Williams's "Move It On Over" with George Thorogood for the soundtrack to the cartoon King of the Hill.

[52] An uncredited review in Billboard magazine called "Best of Intentions" a "gorgeous ballad", comparing it favorably to his early Warner Bros.

Category 5 closed in November 2007 after allegations that the label's chief executive officer, Raymond Termini, had illegally used Medicaid funds to finance it.

[72] In 1994, Tritt made a special appearance as a bull rider in the movie The Cowboy Way, which starred Woody Harrelson, Kiefer Sutherland and Dylan McDermott.

[80] Tritt said that he found his songwriting began to develop during the creation of his demo tape, when he had written a song called "Gambler's Blues" that "felt a lot more connected to Southern rock" than his previous writings.

[22] Stephen Thomas Erlewine contrasts him with contemporaries Clint Black and Alan Jackson, saying that Tritt was "the only one not to wear a [cowboy] hat and the only one to dip into bluesy Southern rock.

"[1] Zell Miller, in the book They Heard Georgia Singing, said that Tritt has an "unerring ability to walk the narrow path between his country heritage and his rock leanings to the acclaim of the devotees of both.

[95] On May 18, 2019, he was in his tour bus when it was involved in a motor vehicle accident that took the lives of two people driving the wrong way on Veteran's Highway leaving Myrtle Beach, South Carolina.

[98] In April 2023, as a protest against Bud Light for supporting transgender influencer Dylan Mulvaney, Tritt Tweeted "I will be deleting all Anheuser-Busch products from my tour hospitality rider.

The show's host, Kim Russo, concluded that an African-American medicine man had been stabbed and beaten to death on the property, and the voices that Tritt was hearing belonged to the murderers' angry spirits.

A title card in the program notes that "On August 14, 1875, a group of men killed a 'hoodoo doctor' close to the land where Travis' cabin was built."