Troy Gentry of Montgomery Gentry Killed in Helicopter Crash

Duo Were in New Jersey for Friday Night Concert

Updated: Friday, Sept. 8, 2017 — 6:05 p.m. ET

Troy Gentry, the more sedate member of the hard-hitting Montgomery Gentry duo, died in a helicopter crash Friday (Sept. 8) in Medford, New Jersey, where the act was booked for a concert at the Flying W Airport & Resort. He was 50 years old.

A native of Lexington, Kentucky, Gentry was born April 5, 1967.

Details of the helicopter crash are still being investigated, but Gentry and the helicopter’s pilot were killed after the aircraft left the Flying W Airport. The helicopter was trying to land when it became distressed around 1 p.m. ET, Medford Township Police Chief Richard Meder told NJ.com.

Although his older partner, Eddie Montgomery, was the scene-stealer onstage with his black hat, ankle-length slicker and mike-swinging antics, Gentry served as the clean-cut and more restrained member of the duo.

Gentry got his music start playing in a band in the early 1990s that included Eddie Montgomery and his younger brother John Michael Montgomery. Gentry then tried for a solo career after winning the Jim Beam National Talent Contest in 1994. The win led to opening concerts for Patty Loveless, Tracy Byrd and Eddie Rabbitt, among others. Unable to secure a record deal, however, he paired with the elder Montgomery into a duo that was finally signed to Columbia Records.

The duo got their big break in 1999, when they went Top 15 with “Hillbilly Shoes.” It helped them establish their rowdy, simple and self-sufficient good-ol’-boy personae that served them so well in such other hits as “Daddy Won’t Sell the Farm,” “She Couldn’t Change Me,” “My Town,” “Hell Yeah” and “Something to be Proud Of.”

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Between 1999 and 2015, the duo released eight albums. Their last No. 1 single, “Roll With Me,” came in 2008, and their last single to chart, “Folks Like Us,” was released in 2015.

In 1999, Montgomery Gentry won the favorite new country artist prize at the American Music Awards. The following year, they won the top new vocal duo and vocal duo of the year honors, respectively, from the Academy of Country Music and the Country Music Association.

They were inducted as Grand Ole Opry members in 2009 and were inducted into the Kentucky Music Hall of Fame in 2015.

The most notorious bump in Gentry’s career path came in 2004 when he bought and killed a black bear in Minnesota that was penned in an electrified enclosure and then passed it off as having been killed in the wild. He subsequently pleaded guilty to the crime, was fined $15,000 and forbidden from hunting, fishing or trapping in the state for five years.

In addition to Friday’s show in New Jersey, Montgomery Gentry’s tour schedule included a Sunday appearance at the Wayne County Fair in Wooster, Ohio. Their tour included 11 other shows in Pennsylvania, Massachusetts, Colorado, Washington, Tennessee, Nevada, Florida and Georgia through the end of October.

Edward Morris is a veteran of country music journalism. He lives in Nashville, Tennessee, and is a frequent contributor to CMT.com.