Photo by Andrew Bless

By Ian Bremner

His bandcamp bio simply reads, “hang in there.” It’s what we’re all trying to do these days. In a signature baritone drawl, Tommy Alexander has a way of saying things as they are. An integral part of the songwriting community in Portland, he is a man with a plan. There is always an underlying strategy, but he operates mostly on feel. He gigs around town with his friends, songwriters in their own right, he runs a booking agency and writes about music himself.

The artistic collective in town has grown into a family, but everyone needs to leave the nest at a certain point. At the time of our chat, Alexander and his wife are packing up for Nashville, Tennessee. It’s not a decision made lightly, but the pandemic has changed everything. Having such strong roots in a city is extremely fortunate, but that support system also allows for spreading the wings and shaking things up. If we’re being honest, the Southwest, Midwest and East Coast is where most of the touring is and for folks like Tommy Alexander, it could be the next best place to release and play more music in 2021.

Ian Bremner: Light and Drama feels connected to your record Waves, but also much different. Both songs seem far more stripped down and direct in a way. Why did you choose to pull these back and release separately?

Tommy Alexander: To be honest, I didn’t know I had them. I was going back listening to cassette tapes because I wanted to clear them to start working on new stuff. I was listening to all of the tapes and those two songs were on the same tape. The cassettes only hold around 20 minutes. Listening back I was like, “shit, these are solid.” It’s just me and the guitar and I didn’t foresee them getting any better and since they were from that time it just felt right.

IB: I noticed Mike Coykendall on the credits. He seems to be a Portland legend and willing to work with a lot of up and coming artists. How did you link up with him?

TA: Mike has become one of my closest friends over the years. We became friends 5 years ago. Now we’re just family. We have a small space together in Portland where we were working in our 4 track studio, then we finished them later on. Mike’s a legend. Yeah, He’s the best

IB: Between the Mama Bird folks, Kassi Valazza, Taylor Kingman, Bart Budwig, Mike and a few other artists, there is quite a collective of you that plays together often. You’ve been playing some socially distanced shows over the last few months. How have those been going?

TA: They’ve been going well. We actually played with the band last night. There’s a venue in town right now, they have an outdoor, 40-seat table situation. There’s pods and people are super respectful of all of the regulations and things. I’m actually heading there right now to see Willy Tea Taylor and Taylor Kingman with our other friend Joshua Thomas and the Turkey Buzzards. Just playing music feels good man. It’s been a year. That’s too much time.

IB: Someone was asking me who I want to see post-pandemic and at this point it doesn’t even matter. I’d kill for an open mic night. I don’t need to hold out for some dream band. Just excited to go back to seeing music.

TA: I’ve only seen the shows I’ve been a part of at the Alberta Street Pub. In a way it’s kinda prime time for us, because as you were saying people just want to see music. I think we’ve played 10 times the past few months and every show sells out. There’s nothing else to do. We just book the show and it’s like “oh hey it sold out again, cool!”

IB: You run a booking company, Pilot Light Booking. Is that purely entrepreneurial, or how did you get started with that type of work?

TA: I was just booking tours for myself and Taylor [Kingman] and we wanted to call it something and he came up with Pilot Light. We started booking tours for Whiskerman and it just started growing from there. I supposed that was 2018. Now three years later we have 42 acts. It’s crazy.

IB: You have a couple other side hustles. You are a fellow music writer and interviewer [for Glidemag]. When you are talking to other songwriters and musicians, does that change your approach to your own songwriting?

TA: It does help assure me of my own approach. I’ve been able to talk to a lot of my favorite songwriters and they all work in pretty similar ways. It kinda makes me feel like there is some common thread running through it all. When I talk to a guy like Brad Barr [The Barr Brothers] and he’s talking about his songwriting process and it lines up with a lot of mine, it makes me feel like “alright, I guess I am not doing this totally wrong.” The main thing is it’s helped me embrace my own process more. 

IB: Things seem to be opening up and becoming more “normal” whatever the hell that means. Your album came out right at the beginning of all this. Does releasing music in a time where you can’t necessarily tour change your approach?

TA: Not really personally. I had to go with what feels good. I had the record [Waves] ready. It would have been nice to tour but I didn’t want to hold it back or anything. I want to put out another full length this year too, so it wasn’t worth waiting around. These two songs were kind of an expression of the moment. I just wanted to share what me and Mike had been working on before I leave for Nashville. I have one more song I want to put out too. Then I will start on my new full length project. Just feels right. It’s more about a feeling than actual strategy.

IB: A bit of a random question, but I noticed you have a quite a famous fan in Michael McDonald of the Doobie Brothers and of course solo fame. How did that happen?

TA: He came to a show of mine in Santa Barbara years back. He just really loved it and came up to me after the show and we became friends ever since. That day, he invited me to come open up for him on tour for the next month. I was already on tour, but the next month I flew back down and did a show with him. That’s the long story short, but it’s been great. That was 4 or 5 years ago. He’s just the coolest guy ever. He’s really an inspirational guy as far as how he treats people. He’s very humble and kind as you can ever hope someone like him to be. I remember being somewhere in Idaho on tour at a rest stop and there was a tour bus driver who had just dropped off Cyndi Lauper and it came up about doing a show with Michael on that tour and the driver was like, “oh, he’s the best.” I had already thought that, but the driver said “No, he really is the coolest out of all of them.” 

Buy and Listen to Light & Drama below