The Songwriter Series: Gregory Alan Isakov

Colorado-based folk singer Gregory Alan Isakov is an artist that’s easy to root for. He’s hard-working, unassuming, and he sings it like he means it.

Originally from Johannesburg, South Africa, Isakov has been turning out tender, deeply poetic songs for some years, catching the attention of several television producers stateside, as well as legions of loyal fans.

We caught up with Gregory on The Songwriter Series this week.


At what point did you know that you wanted to be a songwriter professionally? Was there something that made you realise it was the best thing for you?

“I don’t remember if there was a ‘moment’, per se. I have always written songs, played them to myself in the kitchen for years.

I never wanted to go to school for music because it was too personal at the time. I got a horticulture degree instead and it is my other great passion. During school, I would go out and play the open mics at bars and coffee shops and it was the scariest and most vulnerable feeling that I had ever experienced. I wondered if that feeling would ever go away, and it hasn’t. I’ve become used to it, i guess, but it was important at the time to push myself and do things that scare me.

There were nights I could feel myself and the crowd connecting to the songs in this way I had never experienced before. And it was an incredible feeling.”


Is there a song that you wish you’d written?

“There are so many. Most of Leonard Cohen’s catalogue (especially ‘One of Us Cannot Be Wrong’) and Dylan’s ‘You’re Gonna Make Me Lonesome When You Go’. John Prine’s ‘Mexican Home’ and Sam Beam’s (of Iron and Wine) ‘Trapeze Swinger’.”


Please describe what it is that you experience when you’re on stage.

“The shows are truly the reward of all of it. There are so many days of travel, not knowing where you are gonna be sleeping that night, or if the trains or planes are on schedule. So I find, when I walk on the stage, there is this enormous sense of gratitude and relief.

Every time I play a song – it’s never the same twice. It becomes a completely new experience and I am often amazed how the songs have this life of their own. I guess I try to get myself out of the way as much as possible and really give all of myself to the songs. I guess the overall sense on stage is this humble gratitude to get to do this.”


Is there any chance of a South African tour?

“That would be amazing. I was there visiting family in 2008 and it was the first time being back since I was a kid. I remembered the trees and smells so clearly, its so different than America, but it is so familiar. We visited the house I grew up in, outside of Johannesburg, and it was really remarkable how differently a kid remembers things.”


Is there a song on your setlist that you look forward to playing a little bit more than the others?

“It changes a lot. For the last few shows, I’ve looked forward to the new songs because they are unreleased and there is a certain fresh approach that they naturally have. If there is a song that is unfinished, there is a good chance that if I perform it, the song will finish itself.”


Can you think of a gig, or a moment during a performance, when you realised you were doing something bigger than you had been before?

“I think, as a musician, you always are pushing yourself and doing shows without expectations, because it is a lot of work and like any craft, you are always learning and deepening every day. So each time I am on tour there will be more people at the shows, but I don’t notice it drastically because I may have played that town 10 or 15 times before. But there are definitely moments where I realize that a lot more people are coming out and really connecting with what we are doing.

In the past few years, we have performed in some amazing spaces like Red Rocks Ampitheater, or Telluride Bluegrass Festival, where there will be a moment on stage where I laugh to myself, because I would never have expected to be there. 

There was one moment a few years ago we had the opportunity to open for the Indigo Girls, and they asked me to sing ‘Closer to Fine’ with them during the encore. I remember it got to my verse and there I was singing that familiar song with thousands of people singing with me, it was mind blowing.

A lot of times those moments happen at smaller shows, where I will feel the room become so present and quiet and it feels like everybody is in a dream, and it’s the same dream. I love those moments.”


Is there a songwriter who you love, that you wish more people had heard of?

I really like Nathaniel Rateliff, a friend of mine here in Denver. His songs are remarkable.


What do you hope people take from a Gregory Alan Isakov record?

“I hope  that people feel the vast sense of space that I work so hard at incorporating in the songs. I hope it makes somebody feel small and big at the same time, and that the world around them is beautiful, however lonesome or heartbreaking it can be.”


Keep an eye on the Gregory Alan Isakov Facebook page for tour and record updates. 

Check in this Friday as Gregory Alan Isakov reveals his Top 5 folk songs of all time for The Songwriter Playlists.

Recently, Texan alt country singer David Ramirez picked one of Gregory’s songs for his Playlist – check it out.


Last time on The Songwriter Series: Horse Feathers’ Justin Ringle.



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