Teddy Robb knows when to play his hand. He’s a high-stakes gambling man, you could say. During his business studies at Kent State University, he woke up one morning and decided to move to Nashville on a whim. That was seven years ago.
Barely in Music City a year, something told him to head out west. So, Robb packed up his belongings (again) and relocated to a small ski town in Colorado. Set within White River National Forest, Vail lies at the foot of Vail Mountain and boasts one of the most sought after skiing destinations in the country. A crisp, serene, snow-capped mountain ridge frames Vail Ski Resort, and unbeknownst to him, the spontaneous decision sent him on a path to a record deal with Monument Records, under the Sony Music umbrella, and his debut EP.
“I think I did what I had to do. I don’t regret it at all,” he recalls over a recent phone call with American Songwriter. “There might be a few things I would have done differently along the way. Since I’ve taken on this pursuit of making music, I’ve always followed a gut feeling and sometimes even questioning whether it’s right or wrong. But sometimes, it’s so subtle to go left or right. I just had to trust what felt right.”
Colorado possessed a particular kind of allure for him, notably the skiing culture. “This will sound silly, but I needed to go snowboarding a bunch,” he says. “I wanted to go live a wild life that maybe I wouldn’t ever get to do. So, I just did it. I jumped in a car and drove out there.”
During the following year, Robb dove headfirst into studying country and folk music, drawn to lyrics with a particularly offbeat edge. “A few years ago, I might not have understood it, and I might not quite understand what grabs me completely now. It’s when something sounds like I haven’t heard it before, and it still works in what I want to do,” he says.
It was only a matter of time, and a year later, Nashville called him back in again.
However, things didn’t totally click until Robb signed with SMACKSongs, a publishing company housing such Nashville elite songwriters as Shane McAnally, Josh Osborne, Ryan Beaver, and Old Dominion’s Matthew Ramsey. Within his first year, Robb did what most songwriters do. He showed “up everyday with my lunch box and wrote a song,” he remembers. “No matter what, you’re trying to walk out with a song. That first year was scary and exciting, and I started getting into rooms with people who’d been my songwriting heroes. All of a sudden, I’m writing a song with them.”
McAnally became a great source of inspiration, and Robb’s own musical and lyrical identity falls in much the same category. Yet, across his debut EP, there is a distinctness to not only his vocal approach but style ⏤ situated in the contemporary landscape but leaving his own unique imprint. He also combs influence from other songwriting pillars like Ashley Gorley and Tom Shapiro.
“I’d write with them any time they’d like. They’re paving the way for us right now. One of the biggest things I’ve learned is I’m starting to find my crew of people who I click with and can be vulnerable with,” Robb says. “If I go write with one of those legends, there’s a little bit of trying to impress. Then, there’s when you’re writing with your friends and peers. It takes a bit to find those people.”
Robb’s self-titled debut EP culminates years of songwriting, performing countless shows at $150 a pop, and being patient with a timetable lying out of his control. They often say Nashville is a 10-year town, and if he would have known it would take seven years for a debut, he “may have done things differently,” he admits with a laugh. “In my head, I thought I would know sooner whether it was going to happen or not. I figured I’d come down to Nashville, and I’d either get beat up and go home or it’d happen pretty quickly.”
But work kept falling in his lap. So, he stayed. “It almost felt like that no matter how bad things got and how frustrated I was, it was, ‘Well, I can go play this gig for $150 a night and keep food on the table and not have to call my parents to tell them I’m coming home.’ I kept getting onstage night after night and trying to write songs and trying to sing on a microphone. All the while, almost every night like clockwork, I’d go be onstage for three or four hours and make some money.”
Fast forward a few years, and Robb was ready to make a splash. He initially released “Lead Me On” as his debut single, a guitar-soaked romancer that has netted more than 20 million streams on Spotify to-date. Instead of releasing an album or EP then, he decided to trickle out more singles over the ensuing months. “Really Shouldn’t Drink Around You” and the tearful confessional “Tell Me How” arrived in 2019, all smaller puzzle pieces to a much larger picture.
“We had no idea what would happen with ‘Lead Me On.’ When we put it out, we were all excited about it, and it did more than I ever imagined,” he says about his singles-centric release model. “Same thing with ‘Really Shouldn’t Drink Around You’ [nearing on 3.5 million streams]. “You just have to be fluid with all this. As certain songs take off and people gravitate toward certain ones, you might have a different plan come up.”
Holding onto “Lead Me On,” which opens his five-song debut, was a no-brainer. “It was one of the first songs I wrote and saw people light up over. I was writing good songs. Then, I wrote [this song], and I felt everything was different. It was a song,” he reflects. “People started getting fired up. As songwriters, sometimes we don’t even know. We’re so close to all of our songs. Then, you play them, and you have to trust your core group of people and lean on them. Once in a while, you get a song, and you’re like,’“I don’t care what anybody says. This is what I love.’”
Musically, “Me On You,” released in March, fits snuggly against his catalog so far, but for Robb, he looks back at the song as the moment that “changed me as an artist,” he says. An outside cut, written by Ryan Beaver and Deric Ruttan, it was love at first listen. “When I heard this song, I noticed a really clever lyric, and that melody on the chorus crushed me.”
“I typically always fall in love with Ryan’s songs. This was another example of me hearing a unique melody and lyric. There’s a line about Colorado. It took me back out there in my mind. The song had such a vibe to it, and I dreamed about recording songs like this,” he continues. “I’m glad I am able to sing this song most days. It’s a tricky song to nail. That high part is funny; if you nail it, it sounds awesome. If you don’t nail it at the falsetto part, then, it sounds horrible. I love the challenge of dialing in my vocal for this song. I hope I did it justice.”
“Good Love and Good Whiskey,” written by Jesse Frasure, Bart Butler, Chase McGill, and Carey Barlowe, emerges today as the final piece in Robb’s growing musical identity, playful production with quirky wordplay. “Same kind of guy that brings a girl to a bar / With guys like me around / Who knows good love and good whiskey / Ain’t good watered down,” he sings on the chorus.
“I was looking for a song like this,” he says. Producer Matt McGinn found the song and brought it to the table. It hooked Robb immediately. “You have to have a lane, but you can’t always stay exactly in that lane. This song is country music with some awesome guitar licks and solo.”
Start to finish, Teddy Robb’s debut arrives with an indelible cohesion. His voice glues it all together, and the production ─ courtesy of McGinn, Ben Fowler, and McAnally trading off duties ─ proves an ample backdrop. “Ben has such a unique way of doing things. I did start feeling like we had an identity. Now that I’ve been in the studio making more music, I’m like, ‘Wow, are we potentially creating something that is unique to us,’” he says. “I love the quality of where it’s going. Something that did strike me along the way is we are creating our own sound.”
He adds, “That’s the ultimate goal for me ─ to have something that sounds unique. I think the combination of having Shane involved and Ben and my artistic ability ─ you have no choice but to have your own sound. There’s no other combination that’ll be just like that.”