At around five years old, Gerald Edward "Eddie" Montgomery began performing with his parents' band, Harold Montgomery & Kentucky River Express. When Eddie reached his teens he joined his father's band full-time and replaced his mother, Carol, as the group's drummer.
As a teenager, Troy "T-Roy" Gentry began doing guest vocals with area bands and eventually landed a gig with a group in his hometown of Lexington, Kentucky.
Eddie Montgomery and Troy Gentry first played together in Early Tymz, a Lexington, Kentucky, band formed in 1990 and led by Montgomery's younger brother, John Michael Montgomery. After Early Tymz broke up, the Montgomery brothers and Gentry formed another band, Young Country, but both John Michael Montgomery and Troy Gentry both left soon afterwards to pursue solo careers.
Troy Gentry won the 1994 Jim Beam National Talent Search in Nashville, which led to opening slots for Patty Loveless, John Michael Montgomery, Tracy Byrd and Eddie Rabbitt. However, Gentry was unable to find a record deal, so he reunited with Eddie Montgomery to form a duo called Deuce, which played at local nightclubs. The duo later changed its name to Montgomery Gentry, and signed with Columbia Records' Nashville division in 1999.
Montgomery Gentry released its debut single, "Hillbilly Shoes," in early 1999. which peaked at #13 on the country charts and #62 on the Billboard Hot 100.
Eddie Montgomery was diagnosed with prostate cancer in November 2010. The cancer was successfully removed a month later.
Montgomery and his then-wife, Tracy Nunan, opened a steakhouse restaurant in Harrodsburg, Kentucky in 2009. The couple later divorced, and the restaurant became a point of contention in their financial settlement. It closed abruptly in May 2013, and Montgomery was forced to file for bankruptcy. The steakhouse was auctioned off to help settle $12.7 million in defaulted debts to Central Bank & Trust.
Troy Gentry married Angie McClure in late 1999. They have one daughter named Kaylee, who was born on November 13, 2002 in a Nashville area hospital. Kaylee weighed 5 pounds and 1 ounce, and Gentry assisted in the delivery.
Eddie Montgomery told The Boot
that Montgomery Gentry's song selection process for their albums is very collaborative. "For the most part, we agree on everything," he said. "I think, one, because we've known each other for so long, [and] we've got a lot of similar tastes in music. [Gentry] is a little more traditional and a little more Southern rock-ish, to where I'm a little bit more contemporary, but between my vocal style and his vocal style, we can pull it off, doing what I love to do and what he loves to do."
On September 8, 2017, 50-year-old Troy Gentry was killed in a helicopter crash in Medford, New Jersey. The duo was slated to perform that night at the Flying W Airport & Resort.