This past summer, he returned to South Africa with his family, and this time it was a positive experience.

Gregory Alan Isakov: It was amazing. It looks a lot like Colorado, actually.

KB: After you moved to the states, at what age did you start playing music?

GI: Pretty early on. I think I was playing like jazz when I was 11 or 12 through middle school and into high school. My older brother had an electric guitar that I would steal every once in a while. (laughs) Then I started playing acoustic and playing out by the time I was like, 15.

KB: What kind of music did you listen to back then?

GI: My older brother was really into Phish, Rush, and the Doors. My dad was really into Miles Davis…I listened to a lot of jazz, and then Simon & Garfunkel. When CDs first came out, that was one of the ones we got that I listened to over and over again. And I loved Michael Jackson when I was little. I listened to “We Are The World” over and over again.

KB: Really? That’s awesome. Well, it was pretty big back then.

GI: (laughing) Yeah! It was huge in South Africa.

KB: So how did grow in terms of your musical and songwriting skills over the years?

GI: In high school I listened to a lot of Kelly Joe Phelps and the East Coast folk people too. I didn’t sound anything like them, and it used to get me down. At some point I was like, ‘Well, this is what I do.’ It was weird to write music that didn’t sound like them, but I’m sure they got in there somehow.

KB: Well, what’s the point of sounding like someone else? There’s enough of that already and not much creativity involved.

GI: When I was putting out the record [The Sea, The Gambler] that we just put out, I was only listening to like, stand up comedy and talk radio.

KB: You wanted to make absolutely sure that you weren’t subconsciously plagiarizing from anyone, heh?

GI: (laughing) Yeah.

KB: Well, I did pick up a little of your middle school roots there and some jazz on the title track. It popped up as a cool interlude in between the other songs.

GI: We were going for a Tom Waits-y, jazz feel on that.

KB: You’ve got another song “San Francisco” and it feels like you’ve got influences from other parts of the world where you incorporate these stories. Have you done much traveling, and if so, how did those experiences come into your songwriting.

GI: I did a bunch of traveling overseas when I was in high school. I think it definitely still gets in there and why I love it so much…where you can travel and maybe break even.

KB: What stuck in your mind, whether is was seeing different cultures or meeting different people? Are there any stories that you have that kind of stuck out?

GI: I took some time off during high school. I didn’t know what I was doing there. I ended up traveling in the Middle East for like six months, and played a lot of guitar on the streets. I could never do that again, ‘cause I’m so quiet. But getting to experience music in different places and in different ways…touring through the east coast, I always feel like it’s just saturated with songwriters. You think, “Oh, I hope this song is lyrical enough.’ And then when I go through Montana, everyone is just enjoying it and I don’t feel that intensity around it. It’s cool to see different parts of the country that way, musically and see what people are doing.

KB: In the Middle East, where were you traveling and what period of time was that?

GI: I was in 11th grade. I was all over. I went into Syria, Egypt, Jerusalem, and took a few classes at a high school program for a little while. I don’t know why I was so drawn to that part of the world at that time. (laughing) It felt far enough away from my folks and from everyone.

KB: So your folks were cool with letter you go there at such a young age?

GI: Yeah. They’re pretty cool.

KB: So what brought you to Colorado?

GI: After high school I was in this band, and we moved to the city in Philly, and I realized that I hated it, and I hated living in the city. Then I got this hint that I wanted to study horticulture and found a small school in Boulder called Naropa, and they have a great program there. Then I just stuck around. It was hard to leave. I was involved in the writing program as well…that was my other passion.

KB: What kind of writing have you done?

GI: I write every day. Mostly it’s just poems, stories, and stuff like that. Songs just sort of happen for me from mostly away from the guitar and some with the guitar as well…

KB: So some of the writing that you do eventually progresses towards songs?

GI: I think so, yeah. Every time when I get into a funk where I’m not writing songs, I’ll just start writing and within a couple of pages I’ll have something. So I like to keep that as a big part of my life.

KB: Speaking of writing music, how long was this recent album in the making?

GI: It was about a year and a half. I worked on it in between touring and when I was working out on the farm, doing trade for a living and food, when let me focus on it for that year. During that year, I already have another record written. But I was surprised at how long it took.

KB: Well, when you’re funding everything yourself, that can make a difference.

GI: (laughs) Yeah, definitely.

KB: The musicians that accompany you on the album, are those the same one that play with you live?

GI: For the most part, yes.

KB: How did you come to meet them?

GI: The drummer, Jen Gilleran, was a tabla drummer in New York. She found me…she’s really creative with her sound and we just sort of hit it off musically. Jed Bowes plays fiddle with me for like three years now. He’s a carpenter and I do a lot of gardening, so we would do a lot of jobs together and play afterwards. Phil Pucker plays cello with us now, and so far that’s been really good.

KB: So you won the Telluride Songwriting competition this last year. What was that like?

GI: That was weird. (laughs) I felt kind of silly entering, ‘cause I felt like I chose a few things in my life that aren’t competitive. I really wanted to get into the festival, but that’s the only way you can get in. I didn’t think I was going to win at all. I came late to the awards, and I was the only singer that sat down, and I didn’t talk or tell stories, and look at people…

KB: Like pull some Garrison Keller action?

GI: Yeah! Right. Exactly. So I thought, ‘There’s no way that I’m in this genre.’ So I was totally shocked when I won. It was amazing.

KB: What did you win?

GI: They gave me this hand-built, Shanti guitar. I guess it’s worth like $10,000.

KB: Holy crap.

GI: I know. So they presented it to me on the main stage and they let me sell my record in the main stage tent, which was awesome.

KB: I know you’ve open for some pretty big names like Ani Defranco and Fiona Apple. Have you ever gotten to talk or hang out with any of them?

GI: The openers that I’ve gotten have been kind of random, but I’ve gotten along with everyone that I’ve played with. I guess the most meaningful ones have been the Kelly Joe Phelps shows that I just did, just ‘cause he just kills me. He’s such a cool guy. It’s great to see someone doing it the way I’m trying to do it. He doesn’t have a radio hit. He’s really understated but amazing.

KB: So he doesn’t have any ringtones or anything?

GI: (laughs) Exactly. Fiona Apple was really cool. She listened to my whole set. She was really sweet. The Ani DiFranco one, she had just had a kid and didn’t want to talk to anyone. But I understood that, and overall people have been really awesome.

KB: Have you ever played Hotel Utah in San Francisco?

GI: Yeah, I have.

KB: When I was listening to your album I had to remember to ask you about that, because your music would fit perfect with that venue.

GI: It is so rad. I like the balcony in there.

KB: It is like this living room where bands play. It’s funny, because I was there watching…what’s the guy’s name from Red House Painters?

GI: Mark Kozelek?

KB: Right! I was watching him play and there was this chick talking really loud with her boyfriend, sitting in the balcony area right above the stage. And Mark stops the set and reminds her that he’s trying to play, and if she’s more interested in her conversation that maybe she should take it somewhere else. It was hilarious. But that’s kinda how he rolls, or did at that time.

GI: I think it’s great though. The bar should be high, so I think that’s awesome.

KB: Well, he’s been through his trials and tribulations.

GI: Yeah, I don’t know that I would go his route. (laughing)

In November, Gregory’s his route will take him on the road again for a Midwest tour, and then hits California and the Northwest in December. This Friday he plays the 11pm slot for A Moveable Feast at the Walnut Room in Denver.

You can pick up his latest album, The Sea, The Gambler, CD Baby or check out his tunes at myspace.com/gregoryalanisakov.

-Kim Owens, September 20, 2007

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