Photo: Adam Spangler

Westwood Avenue runs through one of Nashville’s leafy, aging Northern suburbs. The houses are a mix of cute, modest craftsman construction. But the trees. Majestic southern sentinels. Incredible draping oaks and maples provide dappled shade during a hot muggy September day. The South slides from Summer to Fall like nowhere else in the country. Smells like hot dirt. Feels like home. It’s always good to return to the South.

I’m getting sentimental. It’s been 25 years since I walked around Nashville like this, alone, wasting time, thinking about, everything, and looking for a place to sneak a joint. Same as it ever was down here and in my brain. Southern suburbs have a strange pull on me, having spent my first 18 years in a couple variations of them. Maybe it’s the weather. Maybe it’s the smell of that Appalachian red clay ground. Maybe they are just more adorable down here—some kind of southern hospitality built into the bricks. Alright, I am getting sentimental. It’s not my native north Atlanta bucolic burbs, but the sights, the sounds, it might as well be. I can hear ‘Blue Sky’ and the soundtrack of my youth bubble up in my memory as I walk past the school yard.

The foothills of the Appalachias are bigger than political lines and stretch from central Georgia across nearly all of Tennessee, and that blue sky covers all. This particular stretch is where Teddy & The Rough Riders, and a full crew of Nashville musicians, came of age. Childhood friends turned into lifelong brothers and bandmates; it’s as if this neighborhood is fueling today’s buzzing scene. I wanted to get a sense of where it all began. I flew in to Nashville to see the boys play a bunch of shows across AmericanaFest, and alas, try to understand what created Teddy, one of the more unique voices in today’s country rock scene. With so many of my generation’s musical titans passing away, it feels particularly ripe to think about what’s happening on the ground as we continue to send our old sixties and seventies heroes up into that big blue sky. (We love you Dickey).

Teddy & The Rough Riders are having a year. They won the 2024 Ameripolitan Awards Honky Tonk Band of the Year in the Spring. Summer was spent putting that award to proof on the road, backing up Emily Nenni across the U.S. and Europe. September brought their first official AmericanaFest showcase—just one of the nine gigs they’re part of in six days. Then some big dates with Nenni and Orville Peck before a month of headlining dates leading up to the new album drop in October.

The momentum feels long overdue for a band working on ten years together and dropping their third critically acclaimed genre-bucking LP in five years. And that’s on top of near non-stop Emily Nenni tours as her career continues to takeoff. This band has always been willin’. Nine shows, six days. Let’s go.

There is no Teddy. Or Teddy is two people. Multi-generational Nashville natives Jack Quiggins and Ryan Jennings are Teddy. The Rough Riders are a carousel of friends and hired guns depending on the situation. Their latest album, Down Home, out this October from Appalachia Record Co., affords the time and space to bring in more players. Out on the road you typically get the three-piece. These days that’s Jack (guitar and vocals), Ryan (bass, vocals), Tim Kuras (drums). But in their hometown for AmericanaFest, folks get half of what the boys call “Teddy’s Deluxe,” when Sean Thompson adds a dueling guitar. For the full Deluxe package, we’d need pedal steeler Andrew Schneider in the mix.

Most everyone who knows them refer to the entire enterprise as “Teddy’s.” It’s a fun formula anchored in and made possible by the song writing. The core tight trio can run through beautifully sharp songs or spin them up into fiery improvisational southern rock hot rods. Smart lyrics delivered by heartwarming harmonies balance the good ol’ fashion guitar shredding to create a warm tone and syrupy rich sound that set Teddy’s apart, even from the long list of cosmic country rock and soul that spilled from the sixties. Teddy’s is not quite that. Not quite anything but themselves. They bring Lowell George and Little Feat to mind, in so much as you can hear their influences, but their sound remains uniquely their own. Place is also important here. Deep South roots establish Teddy’s sound as country. Only when Jack and Ryan come together and drop in the pockets of their shared history does this Frankenstein come alive.

Back to the burbs. Westwood Avenue. Jack and Ryan take me down the side alleys and back streets to Dragon Park, where they used to skate and look for a good place to smoke a joint. “Weirdos with long hair on LSD,” Ryan quips of their teen years together. After nearly a decade living in a 7-bedroom 100-year-old house on Music Row, Ryan recently moved back into this neighborhood that raised him. Jack lives not far away, just like in childhood. Though Jack is technically from the southeast Nashville suburb of Antioch, he spent most of his free time here, skating his teenage blues away along with what he calls this core group of dudes that sticks together today. At the center of this was group was Ryan and Carter Brallier, best friends since birth (their parents were neighbors and friends).

Twenty or so years later, skateboards traded for guitars, these same streets, same trees, same suburbs, same kids. Same as it ever was. “Timeless,” Ryan calls it on a concept record he made with Carter, named aptly, Westwood Ave. I know these guys. I know that’s dangerous to say, but as with so many southern suburban youths, this unique and somewhat in-between cultural experience, was mine as well. You’re southern but you’re not country. You’re connected to the city, but mostly by strip malls and big box stores. It’s a kind of heaven for kids until you start to think everything happening is happening somewhere else. It can make finding yourself a different kind of journey. Where am I turns into who am I as one grows.

“For the longest time,” Jack says over burgers at Brown’s Diner before our stroll down memory lane, “The idea of Teddy’s probably has roots in the fact that we felt we weren’t allowed to play country music, and I feel like people still feel that. Even people that grew up in Nashville are like, ‘I won’t wear a cowboy hat because I’m not country’ or I’m not a hillbilly. And hey, I’m not country. We grew up in the city. We grew up here. We’re locals but we’re not cowboys. I hate horses. But the music is for everybody.”

As they grew, they tried on different hats, explored other tastes. “I played in a psych pop band (the Paperhead),” says Ryan. “For a while we were kids listening to and playing a lot of different stuff, but it was always the lose, the loud, and the simple that we gravitated toward. Whatever was the most fun.”

It started coming together after high school. Ryan and Jack lived in Knoxville together for a few years, which is where the idea of Teddy’s first hatched. On the front porch. Some of the hottest summer days they can remember. Sweating. Passing big bottles of George Dickel around and playing music. Same as it ever was. Aint that country? “We had good neighbors in Knoxville,” says Ryan. “They were like, ‘Hey, just so you know, we open our windows every time you play music.’ We thought that we were always being too loud and stuff, but turned out everybody loved it around there. That’s weirdly special.”

Some school, some music, some dump truck driving. Both Jack and Ryan have fond memories and a love for Knoxville, but it seemed almost without question that they would be back in Nashville before long getting after this new thing. A few years prior, while the boys bounced around schools and jobs in Knoxville, Carter started working at Santa’s Pub, a double-wide trailer-turned-bar-turned honky tonk-turned Nashville legend, where Sunday became Carter’s night to step out from behind the bar with his Ice Cold Pickers and let loose with the locals, newbie wannabes, and anyone else brave enough to step up. The scene set a tone that Carter took to the stage. Anyone is welcome. Leave your ego at the door. The song is the boss here. It did after all evolve out of a karaoke gig.

Photo: Adam Spangler

“It was like a little Velvet Underground for country,” Jack says. “Where it made everybody want to start a band.” Ryan jumps in: “Santa’s Pub. That music. That atmosphere. The people. That scene, still running all these years later; it’s what made it ok to be like, yep, we’re doing this country garage rock thing.”

“We needed to fill the bar on Sundays,” Carter tells me later. “I was running karaoke; I pitched the idea of a house band and a few weeks later Ice Cold Pickers was born. It took awhile to convince Jack and Ryan to come up and play but soon enough once they came home, this became a home.”

And still going 12 years later. What you begin to see is a through line of trust and commitment with this group, an openness and willingness to collaborate with others. They all spring, Carter believes, from that core group of friends. “Teddy’s has it too. The trust that those two guys have. The lack of ego. I don’t know if you get that without them knowing each other since we were kids.” Instead of Dragon Park, just find them at Santa’s.

It’s where Jack met Emily. And Where Emily found her feet to start launching her career. It’s almost hard to overestimate the influence Santa’s had on this group. It was the education the boys didn’t get going to school. The dissertation eventually came in 2019 with their debut album, The Congress of Teddy and The Rough Riders. Self-produced and published, the album set the sound the boys continue to perfect and grow. “Since the beginning, we’ve had a specific sound in mind,” says Jack. “And that branches out really far at times, but it is always streamlined in our own weird way.”

There’s no tricks to the Teddy’s sound. Anyone can witness it come alive. Rich telecaster tones. A bouncing backline. Honeyed harmonies. A little irreverence. A lot of love. The kind of stuff a soloist dreams of. Enter pedal steeler Luke Schneider. Enter Sean Thompson. Two friends who wanted in. That’s how we get Teddy’s Deluxe. The Teddy’s universe can pull you in. It was through Luke that the band met Margo Price, who produced their sophomore album. It was 2020 and things seemed to be going up and up for the spaceship Teddy.

“I do feel like COVID uniquely fucked us,” Ryan says. “We just happened to be lining up things around that record when it all stopped. We were on our way to play Luck Reunion with Emily and everything got canceled. We got back to Nashville. No jobs. No nothing.”

When they weren’t looking for work they made music. It was during this rich recording period they shared studio time with Thompson, who created the next Weird Ears album, Head in the Sand, due February. When not in the studio, Teddy’s spent a ton of time, literally, Down Home in the basement, featured on the album’s cover.

It may not have happened just as they’d planned it, but they came out of the pandemic on equal footing and with a new album, albeit later than they would have liked, because here we are, and it’s almost 2025. The boys are busier than ever and have songs in the bag they are ready to release, even as they tour the new record.

“We need to find a way to get music out faster,” Ryan says. “But we need to get paid too, because we don’t have time to hold real jobs anymore.”

“It’s funny,” Jacks says. “I like to work. We do work. A lot of days, it’s like I’m right back behind the wheel of that dump truck.”

Afternoon was waning and there was a gig to prepare for. We finished our Teddy’s walking tour at the haunt of haunts, Dragon Park.

“C’mon, climb up on the dragon,” I urge them. The Teddy’s boys oblige and Jack scampers up the 10-foot tall dragon torso, dipping in and out of the concrete as if a serpent breed. “That’s the house where we got weed. Aw man, these are the same concrete panels we used to skate.”

“It’s barely changed some of this,” Ryan says, his head on a swivel taking it all in. I pull on a vape pen and exhale all the stress that doesn’t matter to the blue sky above. These really are the days, I think, doing a whole lot of nothing is my favorite, swapping stories and good times. It’s like we’re walking through a Teddy’s song. I got a friend who said something a few years ago that has stuck with me. Lots of good things in life. Few things better than kicking around, smoking onies with the boys. He was a mid-west suburb kid. Same as it ever was.