The Top 15 Songs From 49 Winchester, One Of Year’s Biggest Breakout Acts

49 winchester country music
Joshua Black Wilkins

Is it too early to say that 49 Winchester should win every “Best Band of the Year” award for 2022?

Not in my opinion, these guys have been on an absolute heater all year long. Call it a breakout year, call it a long time coming, call it whatever you want, just don’t call it a surprise.

Because here at Whiskey Riff, we’ve been telling you this would happen for quite some time.

No bands out there deserve it more, either. The Appalachian soul outfit has blazed their own trail over the last decade and finally began to receive some of the recognition they deserved as they gained momentum with the release of their aptly titled third album III back in 2020.

And they haven’t stopped to catch their breath since.

Hailing from Castlewood, Virginia, the boys hit the road hard, winning over fans in different markets across the country with their high energy live shows. They continued to hone their craft and by February of this year, they debuted their lead single off of Fortune Favors the Bold, “Annabel.”

Gaining momentum with each single release, and with more and more recognition in the music media, 49 Winchester had fans foaming at the mouth for their highly anticipated fourth album Fortune Favors the Bold.

And they delivered one of the best albums of the year.

The 10 song tracklist weaves gracefully between honky tonk heartbreakers and boot stomping barn burners, masterfully capturing the highs and lows of life on the road as well as life in the heart of Appalachia. The lyrics, written entirely by frontman Isaac Gibson, paint a vivid image of these concepts in a way that beautifully juxtaposes his dynamic vocals with the heavy content of the music. And it’s a powerful thing.

We have the rest of 49 Winchester to thank as well though, because if it weren’t for bassist Chase Chafin, guitarist Bus Shelton, Noah Patrick on pedal steel, Tim Hall on keys, and drummer Justin Louthian, Fortune Favors the Bold may not have come to fruition.

If the album is enough, these road dogs are on their way to triple digit shows this year, and many of them have been high profile.

They played over 20 shows supporting Whiskey Myers across the country on their Tornillo Tour and opened for the legendary Turnpike Troubadours at the hallowed Ryman Auditorium as well as a recent sold out show at The Whitewater Amphitheater in New Braunfels.

Throughout 2022, they have also found themselves on the bill at several festivals including Austin’s SXSW, FloydFest, Bristol Rhythm and Roots, Mile 0 Fest, and many more.

Perhaps most notably, they have headlined tons of shows themselves, including their long-awaited Grand Ole Opry debut on August 30. These guys have done it all this year, and proved that fortune truly does favor the bold.

With all that being said, if you have somehow managed to make it this far without giving them a listen, I have listed fifteen of my favorite 49 Winchester songs at the moment, and highly recommend anybody who isn’t familiar changes that.

Check them out here:

15. “Michigan” – 49 Winchester (2014)

14. “All I Need” – Fortune Favors the Bold (2022)

13. “It’s a Shame” – III (2020)

12. “Annabel” – Fortune Favors the Bold (2022)

11. “Fool Hearted” – The Wind (2018)

10. “Long Hard Life” – III (2020)

“Well I done the best I could but I still wound up in jail
And I asked my little wife if she would come and go my bail
But she done spent all of my money
Now I’m sitting in this cell & it’s a long hard life

Well there just ain’t no damn jobs
You gotta do all that you can
Well you got to make your money
Raise your youngins like a man
But the hand that used to feed me just got shut down by the man
And it’s a long hard life…”

9. “Hillbilly Daydream” – Fortune Favors the Bold (2022)

8. “Fortune Favors the Bold” – Fortune Favors the Bold (2022)

“I could sit here on this couch all day
Wish my whole damn life away
Or I could get up off my ass and grab the bull by the horns
Still young enough and dumb enough to grow up fast
But I’ll save that part for last
I’m gonna take every chance I can for this rock ‘n roll
Fortune favors the bold…”

7. “Everlasting Lover” – III (2020)

6. “Raleigh” – III (2020)

“And I know your heart is hurtin’ and I know your back is too
And I know you’re almost certain that I’m no good for you
But just give me a shot, honey give me a chance
I’ll make you laugh, I’ll make you dance

Thank God the jukebox had George Jones
You wouldn’t have known all the words, it would’ve left you there all alone
‘Cause you look like some trouble wearin’ red
And I ain’t the kinda man that needs that runnin’ through his head…”

5. “Russell County Line” – Fortune Favors the Bold (2022)

4. “Chemistry” – III (2020)

3. “Damn Darlin’” – Fortune Favors the Bold (2022)

2. “Veruca Salt” – The Wind (2018)

1. “Hays, Kansas” – III (2020)

Like what you heard?

You’d be crazy if you didn’t.

These guys still have several shows scheduled for the rest of the year, including next weekend’s Greenville Country Music Fest.

Get out and there and see a show.

A beer bottle on a dock



A beer bottle on a dock