Remembering Troy Gentry With Many Off-Stage Moments

Montgomery Gentry

The country music community was shaken Friday (September 8 2017) when Troy Gentry, one half of the award-winning duo Montgomery Gentry, was tragically killed. Gentry passed away from injuries sustained in a helicopter accident at the Flying W Airport in Medford, New Jersey. The aircraft’s pilot also perished in the incident.

Gentry left behind a wife and two daughters along with millions of heartbroken fans around the world, including his fellow country artists who have taken to social media to share memories of their beloved friend.

In remembrance of Troy Gentry, we would like to share some of our favorite memories. Known for his quick smile, incredible voice and his amazing sense of humor, Troy Gentry was never afraid to show off his goofy side. Below are some of our favorite, and funniest, Troy Gentry memories.

1. Meet Troy’s Hysterical Alter-Ego ‘Cowboy Joe’ In This Throwback Parody

Sporting one of the biggest cowboy hats we’ve ever seen, country music singing sensation Troy Gentry unveils ‘the man behind the hat’ in this funny video!

Ripped from the video archives of their behind-the-scenes footage, this hilarious 2008 segment is titled “Tea Is For Texas” and pokes fun at the comically-large items you can buy throughout the state – emphasizing that “everything is bigger in Texas”.

The easily-excitable ‘Cowboy Joe’ pops onto the screen yammering about what’s on the menu for the show that day and quickly bursts into song before heading over to the fridge and fixin’ himself a drink, but when he is handed a spoon that’s bigger than a broom – all bets are off!


2. Eddie & Troy Pull Epic Prank….And They Can’t Stop Laughing

The boys of Montgomery Gentry are often out on the road with their band and find themselves with down time during stops, every now and again. Well, this time, it appears they found a way to fill the time – at one of their band member’s expense!

Poor Bo is sleeping on the tour bus when Eddie and Troy get the wild idea to scare the living daylights out of him!

The whole prank takes all but 10 seconds, but for the entire duration of the rest of the video Eddie and Troy are laughing uncontrollably, with Troy doubled over!


3. Troy Takes The Blazin’ Hot Wings Challenge

Heading to Buffalo Wild Wings, the boys from Montgomery Gentry get Troy to compete against the likes of some tough people already on the wall of fame in a test to see just how much heat he can handle!

The special sauce BWW uses for the “Blazin'” competition is rated at almost 300,000 Scoville units – which makes it 60 times hotter than a raw jalepeno pepper and matches with some of the hottest habanero peppers available!

If, after 6 tortuous minutes, you’ve eaten all of the desperately hot wings and not cried uncle or tapped out – the restaurant will give you a commemorative tee shirt, a photo on the wall, and endless bragging rights!

Are you ready to find out how far our boy Troy got in this super spicy challenge?

We’ll give you a hint: he’s not a quitter!


4. Troy Tells Eddie He’s Going To Shave His Beard, But When He Turns Around? Hilarious! 

In a goofy attempt to shave his beard, Troy ultimately decided to take a break halfway through the process and just enjoy the best of both worlds!

Troy proudly displays the left side of his face to showcase his impressive salt and pepper colored scruff reaching just beyond his sideburn. However, with a quick neck turn, we are unexpectedly presented with a fresh and clean shaven right side of his face!

Troy slowly adjusts his pose and faces the camera head-on, allowing us to see the hysterical side by side view of his creation of a masculine looking man on the left and a clean cut gentleman on the right. What a contrast! His little ruse elicited quite a bit of laughter from his entourage, as well!

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