10 Bars and Restaurants Where Country Stars Got Their Start

In 1989, an obscure country singer performed a show at The Bluebonnet Convention Center in Victoria, Texas. He then sat at the local Walmart for several hours expecting to sign autographs, though there weren’t many takers. Later that same year, after his songs had been flooding the radio, everyone realized what an opportunity they had missed in not getting his autograph, because that struggling artist was none other than the now legendary Garth Brooks.

Though it’s somewhat common to run into celebrities at airports or sporting events, the stories that are truly intriguing are those from before they achieved fame. As is referenced in Dierks Bentley’s 2013 hit “I Hold On,” many country singers get their start in “a million bars, singing every country song. “So, with that in mind, here are 10 places you might have encountered a future country star.

10. Cheatham Street Warehouse – George Strait

george strait at cheatham street
Cheatham Street Warehouse/Ace in the Hole

In 1975 George Strait had just gotten out of the Army, and had joined a band called “Ace in the Hole”, these five guys toured all over central Texas, and had a weekly gig at a San Marcos dance hall known as the Cheatham Street Warehouse. About six years later, George would go on to have a top 10 Billboard hit with his breakout song, “Unwound,” and the rest, as they say, is history.

9. Big O’s Bar – Gretchen Wilson

Though it’s no longer operating, the rough Illinois honky-tonk where the “Redneck Woman” singer got her start tending bar and singing for tips was a real tough joint, complete with bullet holes at the front door. According to the former owner, Mark “Big O” Obermark, Wilson even got into a fist fight at the bar with another waitress. The story goes that the other girl’s glasses were broken in the melee, and Big O paid to replace them. When she came back for a visit after her success, Wilson paid him back with interest and immortalized the bar in her song “Pocahontas Proud.”

8. Deerhurst Resort – Shania Twain

Shania-Twain at Deerhurst
Deerhurst/Shania Twain

In 1987, after her parents both unexpectedly died in a car crash, 21-year-old Eilleen Twain (as she was known in those days) landed herself a job as an entertainer for this Ontario luxury resort to support her four younger siblings. It was several years before her big break in Nashville, and she sang mostly show tunes. Shania still visits Deerhurst from time to time.

7. Chucky Trading Company- Kenny Chesney

It was at this Mexican restaurant in Johnson City, Tenn. that Kenny Chesney got his start singing for $5 per hour plus all the enchiladas he could eat. The restaurant closed in 1998, but the proprietors still maintain a billiard parlor called Numan’s in a downtown Johnson City location.

6. Eddie’s Attic – Jennifer Nettles

Jennifer Nettles Eddie's Attic
Eddie’s Attic/Mike Clifton

You could probably tell from Sugarland’s breakout single “Baby Girl” that Jennifer Nettles is all too familiar with the bar scene. In fact, the blonde crooner got her start at this Decatur, Ga. venue, and credits it with helping her build a fan base. Eddie’s is still hosting open mic nights, and you might just see a future Nashville star there.

5. Nashville South – Jason Aldean

The “Take a Little Ride” singer got his start at the tender age of fifteen, singing with the house band at this Macon, Ga. nightclub. Though it’s now closed, Jason Aldean still remembers his roots playing there.

4. Woodland’s Barbecue – Eric Church

Eric Church/South Caldwell High School Yearbook

The first gig Eric Church ever played was at this cozy North Carolina eatery which still has live music performances every night. Customers hung out so long, occupying restaurant tables to listen to Church sing and play that the waitstaff eventually drove him off.

3. Billie Garner’s Supper Club – Toby Keith

The title track on his 2011 album “Clancy’s Tavern” is an ode to the real-life restaurant owned by Keith’s grandmother. As a kid, he worked in the bar stocking beer and would occasionally join the bands on stage, picking along with a guitar bought for him by his grandma.

2. Libby’s Steakhouse – Jo Dee Messina

Jo Dee Messina was only one of many country music stars who had gigs at Libby’s back in its heyday. The popular Kentucky restaurant even hosted a radio show called “Live at Libby’s” that served as a launching pad for Jo Dee Messina’s career, among others. Sadly, the restaurant burned in 2013.

1. The Tumbleweed – Garth Brooks

Garth Brooks 1989
Garth Brooks/Capitol Records

The same dancehall where he had worked as a bouncer and met his first wife was also one of the first venues Garth Brooks played with his band “Santa Fe” before being signed to a recording contract in Nashville a couple years later. The Tumbleweed is still open and operating, and who knows what future stars might be playing there this weekend?

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10 Bars and Restaurants Where Country Stars Got Their Start