9 Years Ago Today, Half of One of Country Music’s Biggest Duos Died in a Helicopter Crash Days After Recording a Hit Album

On this day (September 8) in 2017, Troy Gentry, one half of Montgomery Gentry, died in a helicopter crash at the age of 50. When he died, the duo had a decade of hits under their belts. They dominated the country charts in the late 1990s and early 2000s with songs like “Lonely and Gone,” “She Couldn’t Change Me,” “My Town,” and the chart-topping “If You Ever Stop Loving Me.” They just finished recording what would have been their first album in three years days before the accident.

Gentry cut his teeth on the Lexington, Kentucky, club circuit. In early 1990, he joined a band called Early Tymz with Eddie Montgomery and his younger brother, John Michael. That group disbanded, and the trio became Young Country, helmed by the younger Montgomery brother. However, he left the group to pursue a solo career and signed with Atlantic Records in 1991.

Gentry decided it was time to do the same. In 1994, he won the Jim Beam National Talent Contest. Then, he landed opening gigs with John Michael Montgomery, Patty Loveless, and Tracy Byrd. However, he couldn’t find a record deal. Eventually, he reunited with the elder Montgomery brother to form Deuce, according to AllMusic. They later changed their name to Montgomery Gentry and signed with Columbia Records. Their debut album, Tattoos and Scars, dropped in April 1999.

The Rise of Montgomery Gentry

Montgomery Gentry hit the ground running. Their debut single, “Hillbilly Shoes,” reached No. 13 on the country chart. Later that year, they hit the top five with “Lonely and Gone.” The album produced three more top 40 hits.

The country music industry took notice. They won Vocal Duo of the Year at the CMA Awards, breaking Brooks & Dunn’s eight-year winning streak. They also took home the Top New Vocal Duo or Group trophy at the ACM Awards.

The duo’s peak chart performance came in the mid-2000s. “If You Ever Stop Loving Me” became their first No. 1 single in 2004. Later that year, they kicked off a four-year streak of top 10 hits with “Gone.” They had topped the charts four more times before the end of the decade with “Something to Be Proud Of,” “Lucky Man,” “Roll with Me,” and “Back When I Knew It All.”

By the mid-2010s, their singles had started slipping down the chart, and their recording schedule slowed. However, they toured regularly and drew large crowds of devoted fans. In fact, they were on tour when Troy Gentry died.

The Death of Troy Gentry

Montgomery Gentry were slated to perform at the Flying W Airport & Resort in Medford, New Jersey, on September 8, 2017. Before the show, Troy Gentry boarded a Schweitzer 269 helicopter piloted by James Evan Robinson for a sightseeing tour. Engine problems brought the helicopter down in a wooded area, killing the pilot instantly. Gentry died hours later, after being rushed to a nearby hospital.

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Montgomery Gentry had finished recording their next album just days before the fatal crash. Here’s to You dropped in February 2018. It peaked at No. 3 on the Top Country Albums chart.

Featured Image by Ethan Miller/Getty Images for ACMA