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Country duo Montgomery Gentry 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. Eddie Montgomery and Troy Gentry first played together in Early Tymz, a Lexington, Kentucky, band led by Montgomery's brother, future country star John Michael Montgomery. Both Eddie and Troy had been performing on the local club scene since their teenage years, the former as a drummer in his father's band. After Early Tymz broke up, a new group called Young Country formed from its ashes, with John Michael billed out front. He eventually went solo, of course, and Montgomery Gentry first formed not long after, initially calling themselves Deuce.
After playing around Lexington for a time, Montgomery Gentry landed a deal with Columbia thanks to a showcase performance. Their debut album, Tattoos & Scars, was released in 1999 and made the country Top Ten on the strength of the Top 20 singles "Hillbilly Shoes" and "Daddy Won't Sell the Farm," plus the Top Five smash "Lonely and Gone" and the Charlie Daniels collaboration "All Night Long." They were named the CMA's Duo of the Year in 2000, breaking a run of eight consecutive years by Brooks & Dunn. In 2001, the follow-up album, Carrying On, was released; it also made the country Top Ten and produced the number two smash "She Couldn't Change Me." A third album, My Town, was completed quickly and released in 2002, bringing the duo their third Top Five hit in the title track.
The hard-driving You Do Your Thing arrived in 2004, followed by the greatest-hits collection Something to Be Proud Of: The Best of 1999-2005 in November of 2005. Some People Change appeared from Columbia Records in 2006, followed by Back When I Knew It All in early 2008. It all amounted to a pretty successful track record, with a dozen or more of their singles since 1999, plus all of their studio albums, entering the Top Ten charts (as did the greatest-hits collection). The duo's eighth studio album, Gravel Road, appeared in 2010. The Michael Knox-produced Rebels on the Run, the duos first album for new label Average Joes Entertainment, appeared in 2011.
Montgomery Gentry is an American country music duo composed of vocalists Eddie Montgomery and Troy Gentry, both natives of Kentucky. The two began performing in the 1990s as part of two different bands with Montgomery's brother, John Michael Montgomery. Although Gentry won a talent contest in 1994, he reunited with Eddie Montgomery after Gentry was unable to find a solo record deal, and Montgomery Gentry was founded in 1999. 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. These albums have produced more than twenty chart singles for the duo on the Billboard Hot Country Songs charts, including the number 1 hits "If You Ever Stop Loving Me", "Something to Be Proud Of", "Lucky Man", "Back When I Knew It All" and "Roll with Me". Ten more of their songs have reached top 10 on the country charts, including the number 3 hit "Gone", the most played country song by a duo in 2005. Tattoos & Scars, My Town and You Do Your Thing are all certified platinum by the Recording Industry Association of America. In 1999, they were awarded Favorite New Artist—Country at the American Music Awards. Both the Academy of Country Music and Country Music Association named them Duo of the Year in 2000, an award for which they have been nominated by both associations in every year since. In 2009, they were inducted into the Grand Ole Opry.
The duo has an as yet untitled new album tentatively set for release on March 24, 2015."Upcoming releases". http://www.hitsdailydouble.com/sales/sales_ur.cgi. Hits Daily Double. Retrieved January 4, 2015. Foster, Ben (18 February 2014). "Montgomery Gentry Sign Record Deal With Blaster Records; New Music Soon". Roughstock. Retrieved 19 February 2014.
Gerald Edward "Eddie" Montgomery was born September 30, 1963, in Danville, Kentucky, and Troy "T-Roy" Gentry was born April 5, 1967, in Lexington, Kentucky. When Montgomery was 13, he played drums in his parents' band, Harold Montgomery and the Country River Express. In 1990, Montgomery founded the band Early Tymz, which included his younger brother, John Michael Montgomery, and Troy Gentry. After Early Tymz broke up, the Montgomery brothers and Gentry briefly performed as Young Country, with John Michael as lead vocalist. John Michael left for a solo career in the early 1990s. Gentry went solo and won the Jim Beam National Talent Contest in 1994, which led to him opening for Patty Loveless and Tracy Byrd. 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. The duo later changed its name to Montgomery Gentry, and signed with Columbia Records' Nashville division in 1999.Whitburn, Joel (2008). Hot Country Songs 1944 to 2008. Record Research, Inc. p. 284. ISBN 0-89820-177-2. Larkin, Colin (2006). The Encyclopedia of Popular Music. Oxford University Press. p. 855. "Montgomery Gentry has new songs to mix in with many hits". Mlive.com. August 2, 2011. Retrieved September 13, 2011. Salkin, Judith (October 26, 2007). "Montgomery Gentry inherit outlaw mantle". The Palm Springs Desert-Sun. Retrieved September 13, 2011. Cite error: The named reference allmusic was invoked but never defined (see the help page). "Montgomery Gentry biography". CMT. Retrieved September 13, 2011.
ContentsMusical career1.1 1999–2000: Tattoos & Scars1.2 2001–2002: Carrying On1.3 2002–2004: My Town1.4 2004–2006: You Do Your Thing and Something To Be Proud Of: The Best Of 1999–20051.5 2006–2007: Some People Change1.6 2008–2009: Back When I Knew It All1.7 2009–2011: Freedom and Hits And More: Life Beside A Gravel Road1.8 2011–2012: Rebels On The Run and Friends and Family1.9 2013–Present: New Studio Album
1999–2000: Tattoos & Scars
Montgomery Gentry released its debut single, "Hillbilly Shoes", in early 1999. It entered the Billboard country singles charts two weeks before its scheduled release date, peaking at number 13 on the country charts and 62 on the Billboard Hot 100. 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.
"Lonely and Gone" was the album's second single, peaking at number 5 on the country charts by year's end. 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. After it, Montgomery Gentry charted the number 31 singles "Self Made Man" and "All Night Long". The latter, which featured guest vocals from Charlie Daniels, was previously the b-side to "Hillbilly Shoes". It was also Daniels' first appearance in the top 40 since "Mister DJ" in 1990. The duo won the Vocal Duo of the Year award at the Country Music Association Awards in late 2000, the first time in eight years that Brooks & Dunn did not win this award. They also won the Top New Vocal Duo or Group award from the Academy of Country Music and the 2000 Favorite New Artist—Country award at the American Music Awards. 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". Tattoos & Scars was certified platinum by the Recording Industry Association of America (RIAA) in 2001, for shipments of one million copies.
The album received generally positive reviews for the duo's Southern rock influences. Thom Jurek of Allmusic gave it four stars out of five, calling it "one of the best pop records of the year. Period." and Alanna Nash of Entertainment Weekly rated it "B", saying that the album was "testosterone-laden". 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.
2001–2002: Carrying On
Montgomery Gentry's second album, Carrying On, was released in mid-2001. Lead-off single "She Couldn't Change Me" peaked at number 2 on the country charts and number 37 on the Hot 100, making their first Top 40 entry there. The album's only other single, "Cold One Comin' On", reached number 23 on the country charts. Also included on the album was a cover of Waylon Jennings' "I'm a Ramblin' Man". In March 2002, they charted at number 45 with the track "Didn't I", a cut from the soundtrack to the film We Were Soldiers which was never officially released as a single. The duo promoted the album both on a headline tour sponsored by Jim Beam, and on the Brooks & Dunn Neon Circus & Wild West Tour, which included Toby Keith and Keith Urban. Later in 2002, they toured with Kenny Chesney on his No Shoes, No Shirt, No Problems tour.
Mike Kraski, then the senior vice president of sales and marketing at Sony Music Nashville, thought that Carrying On showed an artistic growth over Tattoos & Scars, and the duo itself thought that Carrying On was more "edgy" in comparison. It was less favorably received than its predecessor; William Ruhlmann thought that many of the songs "sound like they're trying to [sic] hard to be macho", and Country Standard Time's Mike Clark thought that the duo was "playing it safe", although he described the singles favorably. The album was certified gold for shipments of 500,000 copies.
2002–2004: My Town
On August 27, 2002, Montgomery Gentry released My Town. After working with producer Joe Scaife on their first two albums, they switched to Blake Chancey. 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. They also chose songs co-written by songwriters who had not appeared on their previous albums, including Jeffrey Steele and Rivers Rutherford. The album produced three singles, all co-written by Steele: the title track and "Speed" both at number 5, and "Hell Yeah" at number 4. 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. In March 2004, My Town became the duo's second platinum-certified album.
Ruhlmann gave the album a generally positive review, saying that it "rocks harder as it goes along". On the same site, Rick Cohoon praised "My Town" for "painting in words and music both the pace of living in a small town", and "Speed" for being "slower and more deliberate than the recklessness the title suggests." On Country Standard Time, Tom Netherland called it "their third and finest release".
2004–2006: You Do Your Thing and Something To Be Proud Of: The Best Of 1999–2005
You Do Your Thing, their fourth album, was issued in mid-2004. It was led off by "If You Ever Stop Loving Me", which in mid-2004 became Montgomery Gentry's first number 1 single on the country charts. It was also their biggest hit on the Hot 100, reaching number 30 there. Following it, the album's title track went to number 22 on the country charts, while "Gone" peaked at number 3 and "Something to Be Proud Of" became their second number 1 single. The song spent two weeks at number 1, thus making it the first single for Columbia Records' Nashville division to spend more than one week at number 1 since "Daddy's Money" by Ricochet in 1996. "Gone" was also the most-played single by a country music duo in 2005, and it received a digital gold certification for 500,000 certified music downloads. You Do Your Thing became their third platinum-selling album. Scaife, Chancey, Rutherford, Steele, and Mark Wright split production duties on the album. Steele also co-wrote "Gone" and "Something to Be Proud Of" with Bob DiPiero and Chris Wallin, respectively, while Rutherford and DiPiero co-wrote "If You Ever Stop Loving Me" with Tom Shapiro. In October 2005, You Do Your Thing became the duo's third platinum album. 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." 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." Montgomery Gentry toured in late 2004 – early 2005 with Trace Adkins in support of the album.
"Something to Be Proud Of" also served as the title track to Montgomery Gentry's first greatest hits album, Something to Be Proud Of: The Best of 1999–2005. Also included on this disc were "Didn't I", "Merry Christmas from the Family" and the new song "She Don't Tell Me To" (also co-written by Rutherford, Shapiro and DiPiero), which peaked at number 5 on the country charts in early 2006. Something to Be Proud Of was certified gold.
2006–2007: Some People Change
Some People Change was the title of Montgomery Gentry's fifth album, which was released in 2006 under the production of Rutherford and Wright. Its title track, co-written by Neil Thrasher, Jason Sellers and Michael Dulaney, was previously recorded by Kenny Chesney on his 2004 album When the Sun Goes Down. Gentry told the Edmonton Sun that Some People Change "is based more on family issues, the love of the family, the love of neighbors, relationships", and said that the title track "is about being able to challenge your inner demons and the things that can bring people down, alcoholism, or hatred or racism." Montgomery Gentry's version of the song peaked at number 7, followed by the two-week number 1 hit "Lucky Man" and the number 3 "What Do Ya Think About That". In 2008, "Lucky Man" was nominated for the Grammy Award for Best Country Performance by a Duo or Group with Vocal, the duo's first Grammy nomination.
Some People Change was Montgomery Gentry's lowest-selling album at the time. Joe Galante, then-president of Sony Music Nashville, thought that the album's poor sales were because it "strayed musically from what the base had been. They have an edge to their sound, and I think we got a little too soft." 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". 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". Jurek comparatively called it a "masterpiece" and said that it was "a new pinnacle for the duo", calling the title track "one of those tunes that defines something that lies at the heart of what is good about Americans."
2008–2009: Back When I Knew It All
In 2008, the duo went to the Ardent studios in Memphis, Tennessee to record their sixth album, Back When I Knew It All. Once again, they worked with Blake Chancey as producer. This album's title track, co-written by Trent Willmon, was the duo's fastest-climbing single. Both it and followup "Roll with Me", which included a backing vocal from Five for Fighting, went to number 1. "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. By the middle of the year, this song peaked at number 5. The fourth single, the number 23 "Long Line of Losers", was co-written and previously recorded by Kevin Fowler. Toby Keith, with whom Montgomery Gentry toured in mid-2008, contributed a guest vocal on the Terri Clark co-write "I Pick My Parties", and Lillie Mae Rische of Jypsi made an appearance on "God Knows Who I Am". Thom Jurek wrote of this album, "The hardcore fans will love it, but this isn't the album that will win over many new ones."
On May 26, 2009, Montgomery Gentry was formally invited by Charlie Daniels to become members of the Grand Ole Opry. Marty Stuart and Little Jimmy Dickens inducted them on June 23. Also in May 2009, Cracker Barrel restaurants released an exclusive compilation titled For Our Heroes, which included some of their hits along with "Didn't I" and three other songs which had previously been released only as bonus tracks. The restaurant chain donated a portion of all profits from the album to the Wounded Warrior Project.
2009–2011: Freedom and Hits And More: Life Beside A Gravel Road
On November 30, 2009, Montgomery Gentry released the single "Oughta Be More Songs About That". It was to have been included on an album titled Freedom, which was to have included a song that the two wrote with Gary Hannan and Phil O'Donnell titled "Freedom Never Goes Out of Style". The label scrapped Freedom and instead chose to release an extended play titled Hits and More: Life Beside a Gravel Road, which would have included past hits and three new songs. Its first single, "While You're Still Young", peaked at number 32 in mid-2010. On September 17, 2010, a day before the extended play's slated release, Montgomery Gentry exited the label, and Hits and More was shelved. Both members told Country Weekly that they decided to leave Columbia because "there were so many people trying to encourage us to do something a little different musically. Some of it worked and some of it didn't."
2011–2012: Rebels On The Run and Friends and Family
Montgomery Gentry signed to Average Joes Entertainment, a label co-owned by country rap artist Colt Ford, in March 2011. Their first release for the label, "Where I Come From", appears on their seventh album Rebels on the Run, released on October 18. The album was produced by Michael Knox, who also produces for Jason Aldean. Jurek thought that the album was "the most consistent offering" since Some People Change "even if it doesn't quite scale those heights", and Country Weekly reviewer Jessica Nicholson called it "classic Montgomery Gentry". In early 2012, "Where I Come From" peaked at number 8 on the country charts. It was followed by "So Called Life", which failed to make Top 40.
On October 23, 2012, the duo released a digital-only EP titled Friends and Family. The EP contains four tracks, including "I'll Keep the Kids", which was released as a single.
2013–Present: New Studio Album
The duo spent the better part of 2012 and 2013 touring. They signed to Blaster Records in February 2014 and announced that a new album, to be produced by Michael Knox, would be released within the year. However, the album never appeared, but the duo did issue the album's first single, titled "Headlights", in September. Several websites have reported that the currently untitled album will be released on March 24, 2015, but this has yet to be confirmed by the duo themselves or their record label.Price, Deborah Evans (March 6, 1999). "Strong demand spurs early releases for Columbia's Montgomery Gentry". Billboard (Nielsen Business Media, Inc.) 111 (10): 37, 41. ISSN 0006-2510. Cite error: The named reference whitburn was invoked but never defined (see the help page). Watson, CJ (2003). The Everything Songwriting Book: All You Need to Create and Market Hit Songs. Everything Books. p. 256. Whitburn, p. 114 Huey, Steve. "Montgomery Gentry biography". Allmusic. Retrieved September 16, 2011. Cite error: The named reference mlive was invoked but never defined (see the help page). Cite error: The named reference cmt was invoked but never defined (see the help page). "Search results for Montgomery Gentry". Recording Industry Association of America. Retrieved September 13, 2011. Jurek, Thom. "Tattoos & Scars review". Allmusic. Retrieved September 13, 2011. Nash, Alanna (April 16, 1999). "Tattoos & Scars review". Entertainment Weekly. Retrieved September 13, 2011. Remz, Jeffrey B. "Tattoos & Scars review". Country Standard Time. Retrieved September 13, 2011. Waddell, Ray (March 31, 2001). "Country Duo Montgomery Gentry keeps 'Carrying On'". Billboard (Nielsen Business Media, Inc.) 113 (13). ISSN 0006-2510. Waddell, Ray (August 10, 2002). "Columbia's Montgomery Gentry is rolling back into 'Town'". Billboard (Nielsen Business Media, Inc.) 114 (32): 30. Ruhlmann, William. "Carrying On review". Allmusic. Retrieved September 13, 2011. Clark, Mike. "Carrying On review". Country Standard Time. Retrieved September 13, 2011. Ruhlmann, William. "My Town". Allmusic. Retrieved September 13, 2011. Whitburn, p. 73 Cohoon, Rick. ""My Town" review". Allmusic. Retrieved September 13, 2011. Cohoon, Rick. ""Speed" review". Allmusic. Retrieved September 13, 2011. Netherland, Tom. "My Town review". Country Standard Time. Retrieved September 13, 2011. Jessen, Wade (15 October 2005). "Between the Bullets: Lambert bows as Sony mates hold lead". Billboard: 61. You Do Your Thing (CD booklet). Montgomery Gentry. Columbia Records. 2004. pp. 4–5. 90558. Bell, Rick. "You Do Your Thing review". Country Standard Time. Retrieved September 13, 2011. Jurek, Thom. "You Do Your Thing review". Allmusic. Retrieved September 13, 2011. "Montgomery Gentry, Adkins Schedule 2005 Tour". CMT. December 7, 2004. Retrieved September 16, 2011. Jurek, Thom. "Some People Change review". Allmusic. Retrieved October 13, 2011. Erlewine, Stephen Thomas. "When the Sun Goes Down review". Allmusic. Retrieved September 13, 2011. Ross, Mike (August 4, 2006). "Montgomery Gentry oppose the fighting". Canoe.ca. Retrieved September 13, 2011. Vaught, Larry (December 6, 2007). "Breaking News: Montgomery Gentry nominated for Grammy Award". Central Kentucky News. Retrieved September 16, 2011. "Montgomery Gentry gets "Back" in focus on new album". Yahoo! Music. May 16, 2008. Retrieved November 10, 2008. Sanneh, Kelefa (October 23, 2006). "Critics' Choice: New CD's". The New York Times. Retrieved September 13, 2011. Willman, Chris (October 20, 2006). "Some People Change review". Entertainment Weekly. Retrieved September 13, 2011. "Montgomery Gentry release new disc June 10". Country Standard Time. March 31, 2008. Retrieved September 13, 2011. Jurek, Thom. "Back When I Knew It All review". Allmusic. Retrieved September 16, 2011. "Montgomery Gentry Looks to Get "Raucous"". Great American Country. April 24, 2008. Retrieved October 13, 2011. "Montgomery Gentry inducted into Grand Ole Opry". Associated Press. June 24, 2009. Retrieved September 13, 2011. "CMT Insider: Montgomery Gentry CD Assists Wounded Warrior Project". CMT. June 2, 2009. Retrieved October 13, 2011. Graff, Gary (January 12, 2010). "Montgomery Gentry "Freedom" Album Preview". Billboard. Retrieved September 13, 2011. Horner, Marianne (September 17, 2010). "Montgomery Gentry Leave Columbia Records". The Boot. Retrieved September 17, 2010. "Montgomery Gentry Ship New Single, "While You're Still Young"". CMT. April 19, 2010. Retrieved June 19, 2010. Cite error: The named reference butt was invoked but never defined (see the help page). "Montgomery Gentry sign to Average Joe's Entertainment". CMT. March 4, 2011. Retrieved March 4, 2011. Thompson, Gayle (August 18, 2011). "Montgomery Gentry Are 'Rebels on the Run'". The Boot. Retrieved September 13, 2011. "Rebels on the Run". Allmusic. Retrieved October 13, 2011. Conaway, Alanna (August 19, 2011). "Montgomery Gentry to Release New ‘Rebels on the Run’ Album on October 4". Taste of Country. Retrieved September 21, 2011. Jurek, Thom. "Rebels on the Run review". Allmusic. Retrieved October 21, 2011. Nicholson, Jessica (October 31, 2011). "Reviews". Country Weekly 18 (45): 56. ISSN 1074-3235. Wyland, Sarah (24 October 2012). "Montgomery Gentry Releases Friends and Family EP". Great American Country. Retrieved 28 July 2013. http://www.montgomerygentry.com/329-blaster-records-signs-montgomery-gentry http://www.montgomerygentry.com/337-montgomery-gentry-s-energy-shines-on-headlights "Upcoming releases". http://www.hitsdailydouble.com/sales/sales_ur.cgi. Hits Daily Double. Retrieved January 4, 2015. Foster, Ben (18 February 2014). "Montgomery Gentry Sign Record Deal With Blaster Records; New Music Soon". Roughstock. Retrieved 19 February 2014.
Montgomery Gentry's sound is defined by Southern rock influences. 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." They cite Daniels, Lynyrd Skynyrd and Hank Williams, Jr. as primary musical influences. Montgomery and Gentry alternate as lead vocalists, with Gentry often accompanying on acoustic guitar. Jurek wrote that "Montgomery's rough hewn baritone and Gentry's almost unreal range and trademark phrasing make something highly original". 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 writes 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".
Many of the duo's mid-tempo songs, such as "My Town", centralize on a theme of rural life. Others, such as "You Do Your Thing" and "Some People Change", have messages of tolerance towards others with differing opinions.Cite error: The named reference allmusic was invoked but never defined (see the help page). Gray, Michael (May 4, 2001). "Montgomery Gentry 'Carrying On' With Macho Country". CMT. Retrieved September 16, 2011. Cite error: The named reference mlive was invoked but never defined (see the help page). Cite error: The named reference tattoos was invoked but never defined (see the help page). Carlin, Richard (2006). Country. Infobase Publishing. p. 142. Cite error: The named reference my_town was invoked but never defined (see the help page). Cite error: The named reference ydyt_amg was invoked but never defined (see the help page). Cite error: The named reference edmonton was invoked but never defined (see the help page).
In 2004, Gentry purchased a black bear from a facility called the Minnesota Wildlife Connection and shot the bear from inside an electrified enclosure, commonly known as a "canned hunting". On November 27, 2006, Gentry pleaded guilty to a charge of falsely tagging a bear that was killed in a fenced enclosure as if it had been killed in the wild. Under the plea agreement, he agreed to pay a $15,000 fine, give up hunting, fishing and trapping in Minnesota for 5 years, and forfeit both the stuffed bear and the bow used to shoot the animal in 2004. Gentry posted a statement on the duo's website on November 9, 2010, apologizing for his actions as well as the unethical manner in which he killed the animal.
In November 2010, Montgomery told Great American Country that he had been diagnosed with prostate cancer. The cancer was successfully removed a month later. The same month, his wife, Tracy, announced their divorce, and served his papers at Eddie Montgomery's Steakhouse, a restaurant he owned in Harrodsburg, Kentucky. The restaurant closed abruptly in spring, 2013. The couple had four children and had been married for over 20 years. At first, Montgomery posted to Twitter and Facebook that she divorced him because she did not want to "cope with his illness", which she later denied.
Troy Gentry married Angie McClure in late 1999. They have one daughter named Kaylee, born in November 2002; Gentry also has an older daughter, Taylor, from a previous marriage."Troy Gentry pleads guilty to bear charge". Associated Press. November 27, 2006. Retrieved September 13, 2011. Newcomer, Wendy (November 18, 2010). "Eddie Montgomery Diagnosed With Cancer". Great American Country. Retrieved November 19, 2010. Duvall, Erin (December 18, 2010). "Eddie Montgomery Beats Prostate Cancer". The Boot. Retrieved March 4, 2011. Cite error: The named reference rebels was invoked but never defined (see the help page). Paxman, Bob (October 10, 2011). "Back & kickin' butt: Montgomery Gentry whips out a new collection of hard-driving, honky-tonk anthems—just like in the old days". Country Weekly 18 (41): 42–46. ISSN 1074-3235. "Eddie Montgomery's wife sues for divorce". Country Standard Time. December 1, 2010. Retrieved September 16, 2011. "Eddie Montgomery's Wife Says His Cancer Did Not Affect Divorce Decision". CMT. December 2, 2010. Retrieved September 16, 2011. Chatfield, K.C. (August 22, 1999). "Gary Allan will play Eddie Cochran in upcoming mini-series". Portsmouth Daily Times. Retrieved September 16, 2011. "It's a Girl for Troy Gentry, Wife". CMT. November 14, 2002. Retrieved September 16, 2011. "Stork Is Coming for Sara Evans, Mrs. Gentry". CMT. June 13, 2002. Retrieved September 16, 2011.