If you walk down Division Street in Midtown on a Tuesday night around 11 PM, you’re going to hear it before you see it. It’s a specific kind of roar. Not the polished, over-produced country pop blasting out of the neon-soaked windows on Broadway, but something grittier. That’s the sound of Winners and Losers bar in Nashville. It’s loud. It’s sweaty. Honestly, it’s a bit of a dive, and that’s exactly why people—from broke songwriters to multi-platinum artists—obsess over it.
Most tourists get trapped in the "Nashvegas" bubble of Lower Broadway. They spend four hours waiting for a $22 burger at a celebrity-branded bar while a cover band plays "Wagon Wheel" for the tenth time that hour. There’s nothing inherently wrong with that, I guess, if you like crowds and gift shops. But if you want to know where the people who actually make the music go to blow off steam, you head to Midtown. You head to Winners and Losers.
The Midtown Vibe vs. The Broadway Glitz
Winners and Losers aren't just two bars; they are a symbiotic ecosystem. They sit right next to each other, sharing a wall and a soul, but they cater to slightly different moods. Winners is often where you start—a bit more of that traditional "honky tonk" feel but without the tourist sheen. Losers Bar & Grill is the more famous sibling, known for its patio and the high probability of seeing someone you recognize from an album cover sitting on a plastic stool.
The difference between here and Broadway is the stakes. On Broadway, the musicians are auditioning for your tips. In Midtown, at Winners and Losers bar in Nashville, the musicians are often there to forget they have a job. You might see Riley Green or Chris Young just grabbing a beer. It’s the kind of place where the "no photos" rule isn't written on the wall, but it’s heavily implied by the glare of the regular sitting next to you.
Why Whiskey Jam Changed Everything
You can't talk about Winners and Losers without talking about Whiskey Jam. Back in 2011, Ward Guenther started this Monday night event at Losers. It was basically a way for songwriters and artists to showcase new material in a low-pressure environment. It blew up. It didn’t just grow; it became a cultural institution.
Think about the names that have graced that tiny stage before they were playing stadiums. Luke Combs. Morgan Wallen. Maren Morris. They weren't playing for a crowd of bachelorette parties; they were playing for their peers. That legacy still hangs heavy in the air. Even though Whiskey Jam has grown and sometimes moves to larger venues like Winner's own parking lot or even the Ryman for special occasions, the DNA of the event is rooted in these two bars.
Monday nights in Nashville used to be dead. Now? Monday at Losers is often harder to get into than a Saturday night at most clubs in other cities. It created a "Monday night is the new Friday" culture that defines the local industry.
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What to Expect When You Actually Walk In
Don't show up expecting a craft cocktail menu with artisanal bitters. This isn't that kind of place. You’re here for a cold Miller High Life or a "Bushwacker"—Nashville’s unofficial official drink. If you haven't had one, it’s basically an adult chocolate milkshake that will give you a brain freeze and a hangover simultaneously. It’s delicious.
The layout is tight.
It gets crowded.
People will bump into you.
The walls are covered in memorabilia that feels authentic because it is authentic. It’s not curated by a corporate design firm to look "country." It’s just stuff that’s accumulated over years of late nights and loud music. The wood is worn down. The air smells like a mix of fried food, spilled beer, and a little bit of ambition.
The Food Situation
Losers actually has a legit kitchen. People sleep on the food here because they’re too focused on the stage. The "Loser Burger" is a classic, no-nonsense patty that does the job when you’ve had three too many whiskeys. They do wings, they do fries, and they do them well enough that you don't feel the need to leave to find a Taco Bell at 1 AM. Winners has a slightly different setup, often leaning into that pub-style grub that pairs perfectly with a long afternoon of football or basketball on the TVs.
The "Local" Factor and the Tourist Shift
There’s a tension in Nashville right now. The city is growing so fast that locals are feeling pushed out of their own haunts. For a long time, Midtown was the sanctuary. While the pedal taverns took over Broadway, Midtown stayed for the locals.
However, the secret is out. Winners and Losers bar in Nashville are now on every "Top 10 Things to Do" list. On a weekend, you’ll definitely see the matching t-shirts and the cowboy hats that still have the price tags on them. But somehow, these bars have managed to keep their edge. Maybe it’s the staff. The bartenders here have seen it all and they don't suffer fools. If you’re being a jerk, you’re out. It doesn't matter who you are or how much you’re spending.
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That "no-nonsense" attitude acts as a filter. It keeps the vibe grounded even when the room is packed with people from out of town.
The Secret to Enjoying Winners and Losers
If you want the real experience, don't go on a Saturday night. Go on a Tuesday. Or a Sunday afternoon during football season. That’s when you see the "real" Nashville. You’ll see the session musicians who just finished a six-hour recording date. You’ll see the songwriters who just got their first "cut" on a major record.
Sit at the bar.
Talk to the person next to you.
Don't ask them what they do for a living.
In this town, everyone is "doing something" in music. Asking is considered a bit gauche. Just talk about the game or the beer. That’s how you actually end up hearing the best stories. I once sat next to a guy for two hours talking about vintage motorcycles, only to find out later he wrote three of the biggest country hits of the 90s. That’s the magic of Winners and Losers. It’s a leveling ground.
Navigating the Physical Space
The two bars are located at the corner of Division St and 19th Ave S. Parking is, in a word, a nightmare. Don't even try to find a street spot. There are paid lots nearby, but they are expensive and the predatory towing companies in Nashville are legendary. Just take an Uber or Lyft. It’s cheaper than a ticket or a tow, and you’re probably going to want more than one drink anyway.
Between the two, Losers usually has the bigger crowd and the live music is more front-and-center. Winners has a bit more breathing room and is great for catching a game. They often have an outdoor area that is prime real estate during the Nashville spring and fall.
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Realities of the "Star-Studded" Reputation
You might see a celebrity. You also might not. People go to Winners and Losers bar in Nashville hoping for a TMZ moment, but usually, the "stars" are just there to be normal people. If you see someone famous, the Nashville way is to leave them alone. That’s why they keep coming back. If they get mobbed, they stop coming, and then the bar loses its soul.
The real "stars" of these bars are the house bands. These musicians are world-class. Often, the guy playing guitar in the corner at Losers on a Wednesday is a better player than the headliner you’re paying $150 to see at the Bridgestone Arena. That’s the standard in this town. If you aren't incredible, you don't get the gig at Winners or Losers.
Common Misconceptions
One thing people get wrong is thinking these are "fancy" Nashville spots because of the celebrity ties. They aren't. They are dark, the bathrooms are exactly what you’d expect from a high-volume bar, and the floors might be a little sticky.
Another misconception: that you have to like country music to enjoy it. While the roots are country, the vibe is just "good bar." You’ll hear rock, soul, and plenty of classic covers. It’s about the energy, not just the genre.
Actionable Steps for Your Visit
To get the most out of your trip to Midtown and these iconic spots, keep these tips in mind:
- Timing is everything: If you want to see Whiskey Jam, check their social media (Instagram is best) to see who is playing and where it's happening that night. It often starts around 8 PM on Mondays.
- Dress down: This isn't a "dress to impress" club. Jeans, boots, or sneakers are the move. If you show up in a suit or a formal dress, you’re going to feel very out of place.
- Cash is king: While they take cards, having cash for tips makes the bartenders' lives easier and usually gets you served faster in a crowd.
- Explore the neighborhood: While Winners and Losers are the anchors, don't miss Kung Fu Saloon for arcade games or Rebar for their famous "Bushwacker" variations right around the corner.
- Hydrate: Nashville humidity plus heavy pours can sneak up on you. Drink water between those domestic tallboys.
Winners and Losers represent the bridge between the old Nashville and the new "it" city. They have managed to grow without losing the grit that made them famous in the first place. Whether you end up at Winners or find yourself a "Loser" for the night, you’re participating in a piece of living Nashville history that hasn't been sterilized for the masses yet. Enjoy the noise. It’s the heartbeat of the city.