Troy Gentry, American singer-songwriter and guitarist

Montgomery Gentry, an iconic American country music duo, was forged from the shared musical spirit and Kentucky roots of singers Eddie Montgomery and Troy Gentry. Their high-energy, down-to-earth style quickly made them a beloved act, leaving an indelible mark on the genre.

Their collaboration didn't begin with Montgomery Gentry itself; in the 1990s, they honed their craft performing in different bands, often alongside Eddie's brother, the acclaimed country artist John Michael Montgomery. This period was instrumental in shaping their individual talents and collective chemistry. While Troy Gentry briefly pursued a solo career after winning a talent contest in 1994, fate intervened when a record deal eluded him. He soon reunited with Eddie Montgomery, a pivotal moment that led to the official formation of Montgomery Gentry in 1999, marking the beginning of their remarkable journey.

A Distinctive Sound Rooted in Southern Rock and Country Soul

From the outset, Montgomery Gentry distinguished themselves with a powerful sound deeply infused with Southern rock influences. This meant their music often featured driving guitar riffs, a bluesy edge, and a raw, arena-rock energy that blended seamlessly with traditional country storytelling. Their live shows were legendary for their infectious enthusiasm and rock-and-roll swagger, making them a favorite on the touring circuit.

Their unique style also made them sought-after collaborators. Over the years, they shared the stage and recording studio with an impressive roster of artists, including the legendary fiddler Charlie Daniels, fellow country superstar Toby Keith, the alternative rock band Five for Fighting, and even members of the iconic Southern rock group The Allman Brothers Band. These collaborations further cemented their reputation as genre-bending pioneers within country music.

A Decade of Chart-Topping Hits and Platinum Success

The duo's prolific career saw them release a string of successful albums through Columbia Records' Nashville division. Their debut, Tattoos & Scars, arrived in 1999, quickly followed by Carrying On (2001), My Town (2002), You Do Your Thing (2004), Some People Change (2006), and Back When I Knew It All (2008). A comprehensive Greatest Hits package also commemorated their remarkable output.

These albums weren't just critically acclaimed; they were commercial powerhouses. Montgomery Gentry notched over twenty singles on the prestigious Billboard Hot Country Songs chart. Among their most celebrated tracks were the five No. 1 hits that became anthems for fans: "If You Ever Stop Loving Me," "Something to Be Proud Of," "Lucky Man," "Back When I Knew It All," and "Roll with Me." Beyond their chart-toppers, ten more of their songs climbed into the Top 10, including the poignant No. 3 hit, "Gone," which achieved the remarkable distinction of being the most played country song by a duo in 2005.

Their commercial success was further validated by the Recording Industry Association of America (RIAA), which certified three of their albums—Tattoos & Scars, My Town, and You Do Your Thing—as platinum, signifying sales of over one million units each. This level of consistent success underscored their widespread appeal and impact on the country music landscape.

Acclaim and Induction into the Grand Ole Opry

Beyond sales and chart performance, Montgomery Gentry's talent was recognized with numerous prestigious awards and honors. In 1999, the year their debut album dropped, they were celebrated as Favorite New Artist—Country at the American Music Awards, a testament to their immediate impact. The following year, 2000, saw them earn the coveted Duo of the Year title from both the Academy of Country Music (ACM) and the Country Music Association (CMA).

This early recognition was no fluke; they remained perennial nominees for Duo of the Year by one or both associations every year until 2012, highlighting their sustained excellence and popularity for over a decade. A crowning achievement in their career came in 2009 when they were formally inducted into the Grand Ole Opry, country music's most hallowed stage. This induction solidified their place among the genre's legends, an honor reserved for artists who have made significant and lasting contributions.

A Tragic Loss and a Continuing Legacy

On a somber note, the music world was struck by tragedy on September 8, 2017. Troy Gentry, at the age of 50, died in a helicopter crash in Medford, New Jersey. The duo had been scheduled to perform that very evening. The accident, which also claimed the life of the helicopter pilot at the scene, saw Gentry rushed to the hospital, where he sadly succumbed to his injuries.

This devastating loss left a profound void in the hearts of fans and the country music community. Despite the immense grief, Eddie Montgomery made the heartfelt decision to continue touring under the Montgomery Gentry name, honoring Troy's memory and their shared musical legacy. He has also pursued a solo career, ensuring that the spirit of Montgomery Gentry lives on, echoing in every performance and new release.

Frequently Asked Questions About Montgomery Gentry

When and how was Montgomery Gentry formed?

Montgomery Gentry officially formed in 1999 when Kentucky natives Eddie Montgomery and Troy Gentry reunited. They had previously performed together in various bands during the 1990s, even after Gentry briefly pursued a solo career attempt.

What is Montgomery Gentry's musical style?

Montgomery Gentry is renowned for its distinctive blend of traditional country music with strong Southern rock influences. Their sound often featured powerful vocals, prominent guitar riffs, and a high-energy delivery that made their live performances unforgettable.

What are some of Montgomery Gentry's biggest hits?

The duo achieved significant chart success with five No. 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." Their song "Gone" also reached No. 3 and was the most played country song by a duo in 2005.

Did Montgomery Gentry win any major awards?

Yes, they won Favorite New Artist—Country at the American Music Awards in 1999, and Duo of the Year from both the Academy of Country Music and the Country Music Association in 2000. They were also inducted into the Grand Ole Opry in 2009.

What happened to Troy Gentry?

Troy Gentry tragically died on September 8, 2017, in a helicopter crash in Medford, New Jersey, just hours before a scheduled performance. The helicopter pilot also perished in the accident.

Does Montgomery Gentry still perform?

Following Troy Gentry's death, Eddie Montgomery made the decision to continue performing and touring under the Montgomery Gentry name, preserving the duo's legacy. He also maintains a solo career.