September 9

Troy Gentry Singing ‘Roll with Me’ Video Reminds all to Value Life

Defining tragedy is never easy, especially if the definition involves a very talented man whose voice echoes oozing emotions of hope and making the most out of this very unsure world. 10 years ago, Troy Gentry of Montgomery Gentry sings his heart out on a very rare and unedited performance of ‘Roll with Me,’ a song that would be unfortunately relevant today not only because of his talent but because of his tragic death after a Helicopter plane crash.

Troy Gentry, Beginnings

Troy Gentry was a proud native of Lexington, Kentucky but likes to call Nashville his home. His voice first heard in the country scene in 1990 when Eddie Montgomery formed a band with Gentry and his younger brother, John Michael Montgomery and therefore creating ‘Early Tymz.’ After some time, the trio tried to pursue solo careers with Troy Gentry winning the Jim Bea, National Talent Contest in 1994 which leads to opening of opportunities for other memorable country acts such as Patty Loveless and Tracy Byrd.

Unable to find a record deal after his winning moments, Troy Gentry reunited with Eddie Montgomery to form a duo calling themselves, ‘Deuce’ playing at local nightclubs. Later on, they rebranded themselves to what we have known today as Montgomery Gentry.

Eddie Montgomery tried to clear the air in one of the interviews how their duo was not forced to combine because of industry’s iron fist but because they are friends who happened to jive together musically:

“After artists come to Nashville, then (the labels) put duos together, See, we were friends before we were ever a duo — and so that’s different, I reckon — lifetime friends, man, hanging out together.”

Roll with Me, Troy Gentry

‘Roll With Me’ is a 2008 song of Montgomery Gentry and considered as one of their chart-topping hits that pierce everyone’s soul as the narrative of the song is about a narrator coming to realize what life has to offer and how short it was to focus on things that make us burn bridges and waste opportunities to love harder and live more.

Watch Troy Gentry on this solo act and realize how his lessons echo our perception of our lives:


Roll With Me Lyrics

Wake up in the morning
Get to living my life
Making sure that Im all that I can be
Went to church on Sunday
There was a moment that came
I swear it was like the Lord spoke right to me

So now I’m slowing it down and I’m looking around
And I’m lovin’ this town and I’m doing alright
Aint’ worried ’bout nothing cept for the man I wanna be
I’m thinking maybe it’s time to be livin’ the rhyme
When I’m singing a song about nothing but right
And it’d sure be nice if you would roll with me



roll with me, Troy Gentry

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