Interview: Woody Pines

Years ago I was hosting a party in Nashville, TN, and I wanted to hire a live band to play at the event. While I was quite familiar with the local music that Chicago had to offer, I wasn’t familiar enough with Nashville, but I knew there was a wide variety of talent there. I had rented out The Johnny Cash Museum and had a great set-up, I just needed a great band. Thankfully, a friend of a friend who lived in Nashville gave me a couple of recommendations, and for the vibe I was looking for one band truly stood out. That band was Woody Pines. They dazzled so much the first year my event was in Nashville that I hired them to come back and play again the following year. The band usually consists of three members – Woody Pines himself on lead vocals, guitar and harmonica, plus an upright bassist and a percussionist.

I’ve been following Woody Pines, the individual and the band, ever since those events, hoping to one day see them live again. When Covid-19 hit and performers started canceling live shows (and doing more live streams), I started to notice that Woody was popping up in my Facebook feed more often with regular live stream shows and asking for donations to help support himself during this pandemic. Even more interesting, I learned that he was streaming them from the Dominican Republic. I was curious to learn how he ended up there, and how things were going with his live streams, so I reached out to connect and catch up with him.

The Indy Review (IR): Can you tell me a little more about how you ended up in the Dominican Republic?

Woody Pines (WP): I’m trying to think of a way to condense the story of, “Why I’m in the DR,” to a consumable length, because it is a difficult and long story. [I] came here [on] vacation, sort of an anti-vacation, searching for a cheap Airbnb here on the island as an antithesis for the all-inclusive hotel I was invited to. When I came I made friends and connections, and became part of the community, something that I was missing as a touring musician.

I eventually ended up having opportunities to play gigs and some other beach bars in two or three different towns along the north coast. I came back to build a small career here and my dream was to bring my band. Then the pandemic hit, things closed down, the tourists went home, and I discovered even more what it was like to live in the small village.

I’ve been trying to learn a new language (Spanish) since I am immersed here in the DR and have a Spanish-speaking girlfriend now. Sometimes the days pass so quickly and, since all the regular schedules are out of whack, it’s changed my whole perspective of being a human on the planet really. Luckily, I do have access to some amazing beaches.

It is sort of a “wild west” here – with ex-pats from all over the world, malevolent people, good people, poor people, rich people, sketchy people, sick people – with very few laws, prostitution is legal, drugs are prevalent. Basically, you can do anything you want but you will reap the consequences, and fairly quickly. Never have I played music in a place where the songs, the old blues and country songs from America’s past, seems so real and poignant. There just seems to be a lot of corruption. That said, if you help people and do well and do good, then you bring positive people into your circle. Never have I lived in a place were karma seems to act so quickly.

IR: Has doing these live streams helped you support yourself during these times?

WP: Yes, the live shows on Facebook have really saved my life, allowed me to pay rent, pay my bills, and allow me to keep connected with my own culture and also with my career. It’s amazing to talk with people from England, Scotland, Wales, Germany, and America, and see everybody online from all over the world.


IR: Anything you’d like to tell music fans about surviving during this pandemic?

WP: I have many fears about the healthcare system here being overwhelmed because it is an under-developed government. A lot of the houses in my village are open air with very little, as far as windows and doors – not a lot of room, so people sort of spill out in the street. That said, we have all been wearing masks with pride and pleasure for a long time since March.

– Like and Follow Woody Pines on Facebook to get notified of his livestreams when they happen (you can also view the past livestreams here):

– You can donate to help Woody Pines, as he “sings for [his] supper” at

Woody Pines identifies his music as “hillbilly boogie,” and it’s all delightfully crafted, upbeat, and fun to listen to. You can enjoy all five of his albums in full on Spotify:

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