Remembering The Great Troy Gentry With Some Of Montgomery Gentry’s Biggest Hits

Troy Gentry, Eddie Montgomery are posing for a picture

Man, it’s hard to believe that’s been three years since the country music community said goodbye to the great Troy Gentry.

And honestly, I remember it like it was yesterday. We were in Nashville on “business,” which basically means we took a few meetings and spent of the rest of the time drinking excessively. But, there we were, back in our hotel after going to brunch, about to plot out the day when we heard the devastating news about the helicopter crash.

And it hit HARD…

Growing up on Montgomery Gentry who were always a staple on my mix CDs in the burned CD era, songs like “Speed,” “My Town,” and “Something To Be Proud Of” are still some of my favorite country songs of all time. If I want to throw something on to get the nostalgia going, Montgomery Gentry it is.

Of course, Troy’s life and legacy will continue to live on through the music he created and the countless other artists he’s inspired, so on the three-year anniversary of his tragic death, let’s all take a moment to pause and remember some of these great Montgomery Gentry hits.

“My Town”

Released in 2002, “My Town” is the ultimate small town anthem for anybody anywhere… even if you hate it there.

Who heard it?


My favorite Montgomery Gentry song of all time. Also released in 2002, from their My Town record, this was PEAK Montgomery Gentry.

“Something To be Proud Of”

Released in 2005 on the You Do Your Thing record, the song went on to become the band’s second career #1 single, kicking off a run of 9 straight top 10 singles.

“Hillbilly Shoes”

Chris Stapleton honored Troy with this heart-wrenching performance of “Hillbilly Shoes” on the day he died.

Blake Shelton also performed “Over You” in honor of his late friend at the Troy Gentry Foundation concert at the Grand Ole Opry House.

A beer bottle on a dock



A beer bottle on a dock