People keep typing “who is Troy Gentry” into search bars because of two reasons: his music still gets played on country radio, and his bandmate Eddie Montgomery keeps his name alive on tour every single year. Gentry was one half of Montgomery Gentry, a duo that sold millions of records and became one of the most recognizable acts in country music before his death in 2017. This article lays out exactly who he was, what happened to him, and why his story still matters today.
Background: Who Troy Gentry Was and Why People Search for Him
Troy Lee Gentry was an American country singer and guitarist, born in Lexington, Kentucky. He is best known as one half of Montgomery Gentry, the country duo he formed with fellow Kentucky musician Eddie Montgomery. Together they built a career on what they called “hillbilly honky tonk” — a rowdy blend of traditional country and southern rock that stood out at a time when pop-leaning country was dominating the charts.
Most people search his name for one of three reasons: they just heard one of his old hits on the radio, they’re curious about how he died, or they saw Eddie Montgomery still touring under the Montgomery Gentry name and wondered what happened to the other guy. All three questions lead back to the same story, which this article covers in full.
Latest Update
As of September 9, 2026, here is what’s currently known. There is no new confirmed development in Troy Gentry’s story this week — no new lawsuit ruling, no new statement from his family, and no new health or legal news to report. What is driving search interest right now is timing: September 8, 2025 marked eight years since Gentry died in the helicopter crash, and this year’s date lines up with the ninth anniversary of that crash, which reliably brings a wave of tribute posts, radio retrospectives, and searches every year around this date.
Why he’s trending: Anniversary dates like this one are the single biggest driver of search traffic for artists who have passed away. Eddie Montgomery has a pattern of posting tribute messages around September 8 each year, which tends to spike interest in his late partner all over again.
Separately, Eddie Montgomery has kept the Montgomery Gentry name active on the road throughout 2026, performing at fairs and festivals such as the Linn County Fair in Oregon and the Barboursville Fall Fest in West Virginia under the “Montgomery Gentry featuring Eddie Montgomery” banner. That ongoing touring is part of why casual fans keep discovering — or rediscovering — Troy Gentry’s story years after his death.
Full Profile
Family and Early Life
Troy Lee Gentry was born on April 5, 1967, in Lexington, Kentucky. His mother encouraged his love of music early on, pushing him toward traditional country legends like George Jones and Merle Haggard. He grew up with a brother and sister and spent his teenage years already playing local clubs around Lexington.
Career Path
Gentry’s musical path started with local Kentucky bands, including Early Tymz and Young Country, both of which also involved Eddie Montgomery and Eddie’s brother, John Michael Montgomery. When John Michael went solo, Gentry tried a solo run of his own, winning the Jim Beam National Talent Contest in 1994 and touring as an opening act for Patty Loveless and Tracy Byrd. Going solo full-time proved difficult, so he teamed back up with Eddie Montgomery, and Montgomery Gentry was born.
The duo signed with Columbia and released their debut album, “Tattoos & Scars,” in 1999, which went platinum on the strength of singles like “Hillbilly Shoes” and “Lonely and Gone.” That album also produced a collaboration with Charlie Daniels called “All Night Long,” which helped introduce the pair to fans well outside the usual country radio audience. The record’s success earned them the Academy of Country Music’s Top New Vocal Duo award and, in 2000, the CMA’s Duo of the Year honor, which broke an eight-year winning streak held by Brooks & Dunn.
From there, the duo kept a steady release schedule for nearly two decades. Their 2002 album “Carrying On” reached the Top 50 on the Billboard 200 and went gold. Later that same year, “My Town” pushed them further into the mainstream, spinning off three top-five hits: “Speed,” “Hell Yeah,” and the title track “My Town.” Albums like “You Do Your Thing” (2004), “Some People Changed” (2006), and “Back When I Knew It All” (2008) all cracked the top five on the country charts, and both “My Town” and “You Do Your Thing” eventually went platinum.
Over the following years, Montgomery Gentry racked up five No. 1 country radio hits, including “Roll With Me,” “Back When I Knew It All,” “Lucky Man,” “Something to Be Proud Of,” and “If You Ever Stop Loving Me.” Several of these songs even crossed over onto the pop charts. The duo built their identity around blue-collar, everyman anthems rooted in family, faith, and hard work, and that image, paired with high-energy live shows, is what made them stand out from more polished country acts of the era. Their success was formally recognized when they were inducted into the Grand Ole Opry in 2009 and the Kentucky Music Hall of Fame in 2015. Later albums included “Rebels On the Run” (2011) and “Folks Like Us” (2015), with a final album, “Here’s to You,” released in 2018 after Gentry’s death.
Age
Troy Gentry died at age 50. Had he lived, he would be 59 years old as of this article’s publication in September 2026.
Religion
Gentry’s specific religious affiliation was never publicly detailed in interviews or verified reporting. This detail is unconfirmed and should not be stated as fact.
Spouse/Partner
Gentry was married twice. His first marriage was to Kia Bradley, with whom he had a daughter, Taylor. He later married Angie McClure in 1999, and the couple had a daughter, Kaylee, born in 2002. Angie Gentry survived him at the time of his death.
Net Worth
This figure is genuinely unsettled across sources, so treat any single number with caution. Some outlets reporting near the time of his death cited a net worth in the $8 million to $10 million range built from album sales, touring, and royalties. Other, lower-quality sites have published wildly different figures ranging as low as $1 million and as high as $25 to $30 million. None of these numbers come from an official estate filing or a verified financial disclosure, so his exact net worth remains unconfirmed.
Parents
Troy Gentry was raised by his parents, Lloyd and Patricia Gentry, in Lexington, Kentucky. His mother is often credited in interviews as the one who introduced him to classic country music.
Height
No verified, sourced figure for Troy Gentry’s height could be confirmed through official biographies, major news coverage, or his official band materials. This detail is unconfirmed.
Education
Gentry attended Lexington Community College and later the University of Kentucky, where he majored in marketing and business management before pursuing music full-time.
Hometown/State of Origin
Lexington, Kentucky.
Official Social Media / Website
The band’s official site, which continues to be updated under Eddie Montgomery’s ongoing touring, is montgomerygentry.com.
Quick Facts Table
| Category | Detail |
|---|---|
| Full Name | Troy Lee Gentry |
| Born | April 5, 1967, Lexington, Kentucky |
| Died | September 8, 2017, Medford, New Jersey (age 50) |
| Known For | Co-founder of country duo Montgomery Gentry |
| Bandmate | Eddie Montgomery |
| Debut Album | “Tattoos & Scars” (1999) |
| Notable Hits | “Roll With Me,” “Lucky Man,” “Something to Be Proud Of” |
| Awards | CMA Duo of the Year (2000), Grand Ole Opry induction (2009), Kentucky Music Hall of Fame (2015) |
| Spouse | Angie McClure Gentry (m. 1999); previously married to Kia Bradley |
| Children | Taylor and Kaylee |
| Net Worth | Unconfirmed — estimates range widely, often cited around $8–10 million |
Key date: September 8, 2017 — the day Troy Gentry died in a helicopter crash near Medford, New Jersey, hours before a scheduled Montgomery Gentry concert.A note on rumors: Because Troy Gentry has been gone for nearly a decade, older or recycled headlines sometimes resurface and confuse readers into thinking something new has happened. As of this writing, there is no credible new report changing the established facts of his death. Any claim suggesting otherwise should be treated as unconfirmed until a major outlet reports it directly.
Reader Questions (FAQ)
Is Troy Gentry still alive?
No. Troy Gentry died on September 8, 2017, in a helicopter crash near Medford, New Jersey, at age 50. He was killed hours before Montgomery Gentry was scheduled to perform a concert that night.
How did Troy Gentry die?
He died when a helicopter he was riding in crashed in a wooded area while approaching the Flying W Airport in Medford, New Jersey. The pilot also died in the crash. Investigations later pointed to pilot error and a maintenance failure as contributing causes.
Who was Troy Gentry’s singing partner?
Eddie Montgomery. The two Kentucky natives formed Montgomery Gentry in the late 1990s and stayed partners until Gentry’s death in 2017. Montgomery has continued performing under the Montgomery Gentry name ever since.
Did Montgomery Gentry break up after Troy Gentry died?
Not entirely. Eddie Montgomery kept the band’s name alive and continues to tour as “Montgomery Gentry featuring Eddie Montgomery,” saying the two had promised each other that whoever survived would keep the music going.
Was Troy Gentry married?
Yes. He was married twice — first to Kia Bradley, with whom he had a daughter named Taylor, and later to Angie McClure, with whom he had a daughter named Kaylee. Angie survived him.
What songs was Troy Gentry known for?
As part of Montgomery Gentry, he sang on hits including “Roll With Me,” “Back When I Knew It All,” “Lucky Man,” “Something to Be Proud Of,” and “If You Ever Stop Loving Me,” all of which reached No. 1 on country radio.
How old was Troy Gentry when he died?
He was 50 years old. He was born on April 5, 1967, and died on September 8, 2017.
Wrap-Up
Troy Gentry’s story is really two stories in one: the rise of a Kentucky kid who spent years grinding through local bands before finally breaking through with Montgomery Gentry, and the sudden, jarring way that career was cut short in 2017. The music itself — blue-collar anthems built for truck cabs and county fairs — still gets radio play today, which is a big part of why his name keeps resurfacing in search results almost a decade later.
The other half of the story is Eddie Montgomery, who made a choice a lot of surviving band members don’t make: he kept going. Rather than let Montgomery Gentry end with Troy’s death, Montgomery has spent years touring under the same name, telling interviewers that he made a promise to his old partner long before the crash ever happened. That choice is a big reason Troy Gentry hasn’t faded from the country music conversation the way some artists do after they pass.
If you searched “who is Troy Gentry” hoping for a quick answer: he was a singer, a guitarist, a father, and one half of a genuinely successful country duo, and his death in 2017 didn’t erase the mark he left on the genre. Anniversary dates like the one this article was published near tend to bring his name back into search trends every year, and that’s likely to keep happening for a long time to come.
Thomas Andrew is the founder of Odubio.com, a digital platform sharing inspiring biographies, news, and stories about global icons and achievers.