The duo was scheduled to perform a show on Friday at the Flying W Airport & Resort in Medford, N.J.
The helicopter crashed in a forested area just outside the venue, according to FAA reports cited by Associated Press.
Gentry and a fellow passenger were killed, though it was not immediately clear who was piloting the helicopter.
"Troy Gentry's family wishes to acknowledge all of the kind thoughts and prayers, and asks for privacy at this time."
The duo released its debut album "Tattoos & Scars" in 1999, and went on to score several country chart-topping hits, including ''Lucky Man," "Roll With Me," "Something to Be Proud Of," ''Back When I Knew It All" and "If You Ever Stop Loving Me."
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