The duo is known for its Southern rock influences, and has collaborated with Charlie Daniels, Toby Keith, Five for Fighting, and members of The Allman Brothers Band.

Montgomery Gentry released six studio albums for Columbia Records' Nashville division: Tattoos & Scars (1999), Carrying On (2001), My Town (2002), You Do Your Thing (2004), Some People Change (2006), and Back When I Knew It All (2008), and a Greatest Hits package.

[4] After Early Tymz disbanded, the Montgomery brothers and Gentry briefly performed as Young Country, with John Michael as lead vocalist.

[6] Gentry went solo and won the Jim Beam National Talent Contest in 1994,[3] which led to him opening for Patty Loveless and Tracy Byrd.

[7] Gentry initially wanted to pursue a solo career, but after he was unable to find a record deal, he reunited with Eddie Montgomery to form a duo called Deuce, which played at local nightclubs.

[2] High radio demand for the single led to the label advancing the release date of the duo's debut album, Tattoos & Scars, from early May to April 6.

Following it was the top 20 "Daddy Won't Sell the Farm", which won its co-writer, Canadian country singer Steve Fox, the 2000 Society of Composers, Authors, and Music Publishers of Canada (SOCAN) award for Song of the Year.

[4][7] By the end of 2000, Montgomery Gentry charted at number 38 with a cover of Robert Earl Keen's "Merry Christmas from the Family", itself the b-side to "All Night Long".

[2] Tattoos & Scars was certified platinum by the Recording Industry Association of America (RIAA) in 2001, for shipments of one million copies.

[13] In comparison, Country Standard Time reviewer Jeffrey B. Remz thought that many of the duo's songs lacked distinctiveness, saying that they seemed to be derivative of Daniels and Travis Tritt.

He allowed them to pick different session musicians than typically used on mainstream country albums, such as Chuck Leavell and Johnny Neel of The Allman Brothers Band, whose "Good Clean Fun" was covered on it.

[2] Along with Blake Shelton and Andy Griggs, they contributed a guest appearance on Tracy Byrd's mid-2003 single "The Truth About Men", which made the country top 20.

[11] Rick Bell gave the album a favorable review on Country Standard Time, saying that the duo "unleash [Southern rock] in a torrent of brash lyrics, wailing guitars, and pounding percussion".

[26] Jurek wrote that it "is easily the finest outing by modern country's most relevant duo; it rocks, it's soulful, and it's memorable".

Its title track, co-written by Neil Thrasher, Jason Sellers, and Michael Dulaney,[29] was previously recorded by Kenny Chesney on his 2004 album When the Sun Goes Down.

"[33] Kelefa Sanneh of The New York Times gave a mixed review, saying that it was more "touchy-feely" than You Do Your Thing, and that "no one works a snarling country chorus like Montgomery Gentry".

[34] Chris Willman of Entertainment Weekly gave the album a "C", criticizing the duo for the contradictory viewpoints of personal changes on the title track versus the "defense of the American right to piss off your neighbors" in "What Do Ya Think About That".

"One in Every Crowd", co-written by Montgomery with Kim Tribble and former Trick Pony bassist Ira Dean, was issued in January 2009 as the third single.

Toby Keith, with whom Montgomery Gentry toured in mid-2008, contributed a guest vocal on the Terri Clark co-write "I Pick My Parties",[33][37] and Lillie Mae Rische of Jypsi made an appearance on "God Knows Who I Am".

On September 17, 2010, a day before the extended play's slated release, Montgomery Gentry exited the label,[42] and Hits and More was shelved.

"[44] Montgomery Gentry signed to Average Joes Entertainment, a label co-owned by country rap artist Colt Ford, in March 2011.

[48] Jurek thought that the album was "the most consistent offering" since Some People Change "even if it doesn't quite scale those heights",[49] and Country Weekly reviewer Jessica Nicholson called it "classic Montgomery Gentry".

[55] Following Gentry's death on September 8, 2017, the label announced that the duo had completed their new album prior to the fatal helicopter crash.

Produced by Noah Gordon and Shannon Houchins, the album includes a cover of Merle Haggard's 1983 hit "What Am I Gonna Do (With the Rest of My Life)" and Darrell Scott's "You'll Never Leave Harlan Alive".

[62] On October 29, 2021, Montgomery released his first studio album as a solo artist titled Ain't No Closing Me Down via Average Joes Entertainment label.

Steve Huey of Allmusic wrote that the duo "evokes the sound and spirit of Southern rockers like Lynyrd Skynyrd, the Marshall Tucker Band, and Charlie Daniels, painting themselves as rowdy redneck rebels who still hold small-town values.

[4] Jurek wrote that "Montgomery's rough hewn baritone and Gentry's almost unreal range and trademark phrasing make something highly original".

[12] In his book Country, Richard Carlin describes Montgomery Gentry as "rock[ing] harder than Brooks & Dunn, although their music could be seen as an extension of that successful pair's boot-scootin' sound."

He also wrote that Gentry sings with a "sweet, high tenor" while Montgomery "complements with an earthy, sometimes raspy, baritone", and notes that the duo has an "energetic stage show and dress".

[83] On November 5, 2018, the final National Transportation Safety Board report was issued, with the accident being primarily attributed to the pilot's "failure to maintain rotor rpm... which resulted in an uncontrolled descent.