Eddie Montgomery and Troy Gentry were the ultimate "blue-collar" kings of country music. They had the grit, the black hats, and that unmistakable blend of Southern rock and barroom anthems. But when December rolls around, fans often find themselves scouring Spotify or old CDs looking for a definitive Montgomery Gentry christmas music collection.
They won't find one.
Unlike almost every other major country act of the 2000s—think Alan Jackson, George Strait, or even Rascal Flatts—Montgomery Gentry never actually recorded a full-length Christmas album. It's a weird gap in a career that spanned nearly two decades and dozens of hits. You’d think the guys who sang "My Town" would have a definitive version of "I'll Be Home for Christmas," right?
Well, the reality is more about timing and the specific brand they built. They weren't "polished" artists. They were loud. They were proud. They were about Saturday nights, not necessarily Sunday morning hymns, at least in their public-facing discography.
The Tracks That Actually Exist
Even though there isn't a 12-track LP with them sitting in sleighs on the cover, we do have some rare gems. The most prominent piece of Montgomery Gentry christmas music is their cover of "Merry Christmas from the Family."
Originally written and performed by Robert Earl Keen, this song is the antithesis of a "silent night." It’s about chain-smoking, running out of ice, and relatives who don't necessarily get along. Honestly, it was the perfect fit for them. They recorded it for the Country Christmas compilation (released by Sony) back in the early 2000s.
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It feels authentic. When Troy sings about "tamales and celery," you believe him.
- Merry Christmas from the Family: This is their heavy hitter. It’s rowdy. It’s funny. It fits the "Hell-raisin' talent" vibe they spent years cultivating.
- Christmas in the Country: You can find live versions or various promotional radio spots where the duo performed snippets of holiday classics, but "Merry Christmas from the Family" remains the only studio-quality mainstay.
Why just one? Labels usually push for holiday records because they are "evergreen assets." They sell every year forever. But Montgomery Gentry was focused on a very specific trajectory of high-energy radio singles. A slow, somber Christmas record might have felt like a momentum killer during their peak years between Tattoos & Scars and Some People Change.
The Robert Earl Keen Connection
You can't talk about their holiday output without mentioning Robert Earl Keen. His songwriting influenced a generation of Texas and outlaw country artists. When Montgomery Gentry covered his Christmas song, they didn't try to make it "Nashville pop." They kept the rough edges.
The song describes a dysfunctional but loving family gathering. It mentions "fake snow" and "margarita mix." For fans of MG, this was much more relatable than a choir-backed rendition of "O Holy Night." It reflected the lives of the people who bought their tickets—folks who deal with real-world holiday stress.
Why a Full Album Never Happened
I've spent years tracking country music trends, and usually, the lack of a Christmas album comes down to one of three things: contract disputes, a lack of interest from the artist, or a tragic interruption.
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For Eddie and Troy, it seemed to be a mix of the first two, followed eventually by the third.
By the time they might have been "old enough" in their careers to settle down for a legacy holiday project, the industry was changing. Then, the unthinkable happened in 2017. The helicopter crash that took Troy Gentry’s life in Medford, New Jersey, effectively ended the duo's creative output as a pair.
They had just finished a new album, Here’s To You, which was released posthumously. But there were no holiday tracks in the vault.
It’s a bit of a bummer. Imagine a Montgomery Gentry version of "Run Rudolph Run." It would have been incredible. The guitar riffs alone would have made it a staple at every Southern holiday party.
The Legacy of "Blue Collar" Holidays
Despite the lack of a dedicated discography, the duo’s music often gets lumped into "Country Christmas" playlists anyway. Songs like "Lucky Man" or "Back When I Knew It All" have those themes of gratitude and reflection that spike in popularity during December.
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Fans have even created their own "DIY" Montgomery Gentry holiday playlists. They take the one official song and pad it out with tracks from their peers like Toby Keith or Blake Shelton. It’s a testament to their staying power that people are still looking for Montgomery Gentry christmas music years after Troy's passing.
Where to Find the Rare Tracks
If you're looking to add them to your holiday rotation, don't look for a standalone CD. You have to go digging in the "Various Artists" bins or digital folders.
- Check Sony Music Compilations: Most of their holiday work was licensed through their parent label's big multi-artist packages.
- YouTube Archives: There are several "Grand Ole Opry" holiday performances floating around. These are often the only places to hear them do more traditional carols.
- Bootlegs and Fan Edits: Be careful here, but some long-time fans have cleaned up radio broadcasts from the mid-2000s where the duo sang live in-studio.
Honestly, the "Merry Christmas from the Family" video is a must-watch. It captures that early 2000s country aesthetic perfectly. It reminds us that Christmas isn't always about perfection. Sometimes it's about the chaos.
Actionable Next Steps for Fans
If you want to keep the spirit of MG alive during the holidays, here is how to actually find and organize their limited festive output:
- Search specifically for "Country Christmas (Sony Music Distribution)" on streaming platforms. This is the primary home of their studio holiday recording.
- Create a "Redneck Christmas" playlist that bridges the gap. Pair "Merry Christmas from the Family" with tracks like "The Night Before Christmas" by Jeff Foxworthy or Alan Jackson's "I Only Want You for Christmas."
- Support the Troy Gentry Foundation. If you're feeling the holiday spirit of giving, this foundation continues to do great work in Troy's memory, focusing on cancer research and helping military families.
- Look for "T-R-O-U-B-L-E" era live recordings. Occasionally, 1990s and 2000s radio promo discs surface on eBay that contain "Holiday Greetings" from the duo, which are cool collectors' items.
The music of Montgomery Gentry was always about the people. Even without a 10-song Christmas LP, they gave us enough truth in their music to last several lifetimes of Decembers.