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Photo credit: Ryan Kibby

Photo credit: Ryan Kibby

by Rob Preskill


I spend a lot of my music-loving time pining over eras I thought to be gone, some of which had preceded me. Last month, in a digital moment, a coast-to-coast train named Matt Pless roared through my local indie station playlist just as I was changing frequencies. He was picking and crooning a song called, "I Hope You're Happy Now," which had the most sincere dead-ahead lyrics I had heard in a long time. Chilling lines fell on plucked strings telling me, "You're legacy don't matter any more," causing me to pull my car over on the side of the road, to jot down the song's name.  

Later on, I would call-up YouTube performances, and view a sporadic, short and stunning musical history of someone I hadn't yet discovered. Matt Pless' appearance after appearance in towns all over American, viewed in no particular order, rattled me with this feeling that I'd had several times before, but not in a while. With underground communities of music lovers who open their great rooms and dens to musicians like him, he is just where he should be—making himself at home in your playlist.  There is a difference between the over-produced artist who takes a good impromptu song and places it through committee and the busking street performer who fine tunes his guitar-picking and lyrical scenes until they are worn true like a perfect stone and ready for skipping. Mr. Pless is the latter. Having spent years throughout America playing street corners, bars, and places adjoining other friendly foyers, he is as close as one comes to a folk troubadour today. 

Pless likes to associate himself with his punk roots, especially as folk songwriters go, but be prepared to snap your fingers in appreciation.  Sit still for a few of his songs, and you will find one may change your outlook on life, wittingly recalling other well-word guitar picking tunes while remaining fresh and in the moment.  The themes in some of the songs skip faster than traditional folk—propel you beyond the span or scope of a Woody Guthrie tune. They do not linger on a single story line, but instead weave together patterns we have heard into a new patchwork we haven’t quite seen. Unlike one unmentionable curly-haired, early folk rebel, I talked with him and found him surprisingly open and hopeful while lyrics were wise beyond his years.  He has produced songs that reminisce like, "Ashtray" and "The Book of You and I"; political songs such as, "The Breadline", and the confounding rock riddle called "My Idea of Heaven" as well as ones that wallow in love, drugs and a dark reality like, "I Hope You’re Happy Now" and "The Crayon Song." Older works were re-released on Nostalgia Ain’t What it Used to Be. His 2014 release Songs in the Key of Blue, make the listener sit in disbelief that such pure stuff still buds from the musical tree. There are people who are totally comfortable in their role, and Matt Pless is one of them.  When I talked with him he was in New York City for a few months on the heels of a two year town-to-town tour. 


Q: I look at the music business as being a business and something you have to work at.  I know it’s more than that but is that generally true?  How did you get into this business? How old were you?

MATT PLESS: I don’t look at what I do as a business--I’ve been playing music and writing songs since I was a kid.  Acoustic stuff.  My older band had just fallen apart and I could not find any other musicians to play with, so I started doing acoustic singer songwriter stuff. 

Q: Are you from Baltimore?  Where are you now?

MATT: I was born in Baltimore, yeah. I don’t spend much time there now. I'm spending a lot of time in NYC now. I don’t have a place here, though. I got off this huge two-year and have been spending some time here winding down and getting ready for the next project. 

Q: You say when your band disbanded, it was natural to just keep playing.  You may have been looking for a band but nevertheless, you’re clearly a singer-songwriter. There’s a lot of internal stuff in your lyrics that lend to a solo performance.  I am guessing you've been a busker in the past? It seems like your work has been played and fine-tuned for years. 

MATT: Yeah, I’ve been a busker. I’m actually featured in this book that just came out about New York City buskers called, The Noise Beneath the Apple. That’s a coffee table book.  I worked with that project for a while.

Q: So let's say you’re a 17 year old kid and you’re musically inclined, what do you have to do to get where you are now in terms of making all these songs happen, putting it all together, in terms of arranging and writing this kind of music.

MATT: I have no idea. I just can start writing.  It’s not like I fine tune my stuff in a conscious way. It’s just like I’ve been playing these songs and the fine tuning developed on its own...based on my voice, my experience and the growth of my ability with instruments. If you do anything enough it’s going to make it really tight. Much of how the songs came out is hard for me to explain. Some of the older songs I still play, and some of them I don’t play anymore. There’s a difference in vocal quality and that sort of thing.  A different tone. Nuances.

Q: In a society that’s so goal-oriented, your style of songwriting might be called more organic. Even the career that you’ve developed for yourself is organically based and home grown.

MATT: Yeah, I mean I’m doing it all myself. So, I’m involved in the whole process.  The booking, the touring, the writing. In that sense …yeah. But I've always liked catchy music.  Much of the time, that aspect of my personality actually gets incorporated into my songs on a conscious level. I try to target a natural feeling, a natural melody that comes out of me that I feel strongly about. Natural words. And I craft them into a format or formula of the verse-chorus-verse type thing or like …I like hooks, you know? But they come to me in those unconscious moments; the conscious moments are the ones that let me know if I have come up with a good song during my unconscious moments.

Q: Even in alternative music out there it seems like songwriters are a little afraid of rhyming. You’re not afraid of something that’s catchy. Take for example “My Idea of Heaven” (what I call, The Milkshake Song). Every verse is dizzy with riddles and sing-songy lines that rhyme, and it feels like the riddle is getting heavier and more dangerous, more political, until it ends with punch line. So that’s intentional?

MATT: I like catchy music although I wouldn't say I intentionally write hook laden tunes, but because I gravitate toward catchy melodies, I would say the chances of that influence ending up playing a part in my song writing is pretty high. As far as the "Milkshake Song" I wrote it in 5 minutes during a bout of writer's block when my brother told me to "Just write about anything you think of." I had been listening to this Brooklyn punk band I like a lot called "Crazy and the Brains" when I wrote the lyrics and I think their music influenced me a lot on that one. People seem to really love that song. I dunno what it's about, I think it's a ridiculous bunch of words, it doesn't really have any direct meaning. Someone once told me that it was like a "giant metaphor for nihilism" because the lyrics glorified the consumption of bacon, which is, according to the guy who told me this, "the most unhealthy food in the world." Therefore, unapologetic love for bacon equates to the idea that nothing matters and the future is hopeless. So do what you want right now regardless of how it may affect you later. I think people are reading into it too much. All this talk of riddles and politics [laughs] it's just a song man...

Q: When I hear a song like, “Of Love and Loss,” I know the roots of your music when I’m hearing it but I also keep hearing new things.  You seem unafraid to sound like a traditional folkie though. 

MATT: I just do what I feel depending on where I am in life. I don't care if it sounds like folk music right now, if that's what that song calls for. But there are other sides to what I do too.  As far as the folk music side, the more finger picky stuff, I’m not ashamed of that. It’s cool. 

Q: I noticed you worked on Occupy this Album.  And you’re the first song on the album. Tell me your relationship with the movement and how you met the people who put the album together.

MATT: I was busking for change in Zuccotti Park and this insurance salesman approached me and told me that seeing me play had inspired him to create a benefit album for the Occupy movement.  I ended up scoring the first track on an album that featured a bunch of heavy hitters: Crosby and Nash, Willie Nelson, Jackson Browne, Joan Baez, and a bunch of other musicians. I was never heavily involved in the Occupy Movement however. For as much good as it may have done by shining some light on economic inequality in this country, I had a lot of criticisms in regards to the movement in general. In addition, the producers of the album kept trying to make me THE occupy guy, voice of the revolution, and all that ridiculousness, and I didn't want anything to do with that. Occupy Wall Street had so many voices, singling one particular voice out and putting them at the musical helm just didn't make any sense to me. Occupy Wall Street was something I did, it wasn't 'what I do'.

Q: Sounds like there’s a lot that happened there.

MATT: Yeah I was down there playing music. I was writing about it in my journal of road stories. It was cool though.  There’re all there in a book I have back home.  Maybe one day I’ll put that out.

Q: You wrote a book about it?

MATT: A journal, yeah, I’m trying to write a whole new book now -- about my life. I’m working on it, so that writing will probably be in there. It was definitely a cool experience in my life.

Q: A song like the Crayon Song just blows me away. Is that one of your newer songs?

MATT: It’s kind of old actually. I think I had written it in 2008.  That song has just lasted. People really get into that.  I’m not sure why that one is one of the big ones but it seems to strike a chord with people.

Q: Do you remember writing it? Was it a quick process? A longer process? What do you remember about writing it?

MATT: Yep. I had just learned how to fingerpick in a different style from this guy in New York who saw me playing on the street. He said he learned how to fingerpick from Dave Van Ronk.

Q: What was his name?

MATT: Erik Frandsen. He’s an old school cat from Greenwich Village. When he saw me playing, I was playing this pop rock, I was strummin’.  He’s like, hey man.  “Let me buy you a beer.” I said, “Okay,” He invited me into this tavern. So we're having a drink he’s talking about folk music. … anyway, he taught me how to finger pick in a way I had not learned before. I practiced it and I finally got it and the first thing I wrote with it was "The Crayon Song." I based it on this line I’d been carrying around “…I'm off to wander with my lover in her bag of pretty colors…” It had been in my head for a long time.  I was hanging out in New York City staying up all night with different situations going on and you know, I’d say the whole thing just popped together one day.  It was a combination of learning this finger picking style, hanging out with girls in New York City and my friend’s mother passed away and for whatever reason, she was on my mind. A lot of heavy emotional stuff went into that.

Q: What I noticed is how free the song feels and yet how tightly wound it is. It feels like a perfect song. I just felt that from what I heard in that song. That’s not something I hear a lot.  I listen for it but it’s not everyday that I hear new music like that.

MATT: I appreciate that.


Q: Your music strikes me as having a healthy dose of innocence, forward projecting cynicism, hope, and wisdom.  How old are you, first of all. And how old do you feel?

MATT: I feel much younger than that now [laughs]. I think between Generation X and Millennials.  I play to those age groups mostly these days on the DIY circuit. Many listening to my music in a heavy way were born from 1975 to 1995—that folkie side seems to grab the Boomers. I think the Gen X-ers are more cynical and apathetic about things and the millennial are more optimistic--I was between that, so there’s part of me that’s more cynical and a part that’s hopeful. I try to look at the big picture, I know how easy it is to get stuck in tunnel vision. I look at the big picture as much as I can. Sometimes I think the more extreme your songs are, the farther you go in one direction, the harder it is to get your point across.

Q: Do you have a song you love the most right now as you are playing out.

MATT: Right now?  I love this new song called, "The Boy in the Bottle." It’s not recorded yet.  I like everything that’s a brand new song. I always like playing "The Crayon Song" though. It’s a relaxing song. When I play that, it feels very meditative--and I get centered and everything’s secure. With that song, everything goes away. Also, that song "Ashtray" – it seems that certain audiences will sing along with that one. That’s always fun too.

Q: I noticed that you had a tour last year. It seemed like you went across the country recently. Did you take a bus? How did you get around? 

MATT: I took my Ford Focus. I’ve been across the country a bunch of times on tours. Most recently, I left in 2013, and I’ve been on the road pretty much ever since. Before that I was touring more regionally ever since November 2012. So it’s been me driving around in my car. Playing house shows, living rooms, bars, coffee shops. 

Q: Can you name some towns?  Maybe some of your favorite little towns?

MATT: Many times, I find the small unknown towns have the best shows, mainly because people in those areas are starving for entertainment, or some event or happening that will break through the monotony for a little while. I have been around the United States performing on tour 15 times now. I can safely say I have had great times and really fun shows in Buffalo, New York, at a place called the Hoyt house. there is a great DIY scene in Buffalo, lots of house and basement venues. Stockton California has shown me a lot of love, as well as the folks in Denver, Colorado. There is a really great Venue there called The 7th Circle Music Collective that always has really fun and well attended shows. I make it a point to book a show there during every tour. Fort Collins, Colorado, is also a wonderful place.  I love the mom and pop hippie community vibe that runs through that town. I have had really fun shows in Savannah, Georgia--there seems to be a pretty active scene down there. I really dig hanging out on the West coast, southern California has a pretty active scene for folk music and "folk punk,"  if you are into that type of thing....but I mainly enjoy that part of the country just because it's California and everything out there feels like it's exploding with possibility and sunshine. New York City will always be close to my heart. I learned so much from the time I spent living in that town. Every serious artist should spend some time in New York City. Then there are random towns like Oklahoma City, Chesterton, Indiana, or Huntsville, Alabama. The list of cool towns with interesting things happening is endless...I hope I never stop discovering new places.

Q: Do you have a lot of friends nationally, or are you getting followed on line so you have that crowd? How do you find your communities?

MATT: It just kind of happened, man. There’s this record label called Plan-it X Records. That label has a lot of music that falls in the same line as some of the stuff I’m doing. I was advised to play their festival a couple years back: Plan-It-X Music Festival in Bloomington, Indiana. A lot of bands play, and kids come out from all over the country. I went there with a hundred CDs and I gave them all out.  It was like a bomb, a grenade. All these kids went back to their little towns and said, “Hey, come play here, come play here.”  I started connecting the dots in asking friends I had met to fill the gaps in where I didn't know people and I kept building it off of that. You meet people, you make friends with them. You help them out when they come to your town. Try to help them with shows and contacts. It’s a real cool community atmosphere and the Internet makes it real easy to network with these folks, many are progressive thinking, you learn a lot, you see a lot and there’s a lot of good music too.

Q: When you drive, you drive alone?

MATT: Basically yeah. Sometimes I take people with me. I went on tour with a friend of mine. Francie Moon. I was with her 7 or 8 months out of the year. She played shows with me. People at shows are really cool.  They donate at the door, and nobody’s ever turned away. You can make a little money and we sell merchandise. I usually eat food with the amount coming from merch. And the door money goes to the gas tank so you can do pretty well.  You sleep on couches, and people feed you a lot. You meet people on a level that you wouldn’t necessarily meet at a bar. You’re at a house just hanging out and then they take your music and they tell their friends.  All of a sudden you have a fan base in town.

Q: So you play a lot of house shows?

MATT: I like playing bars and places like that but I noticed people at house shows pay attention much more. For lyrical music of any sort, people tend to want to listen more.  At a bar they might not necessarily hear what you are saying.  A lot of the time you’re going to play to what sounds like a high school cafeteria. 

Q: When I think about the fact that you drive around the country and your concerts can take place in a community around someone’s living room, I can't help but contrast that with the insulated environment many peoeple are in. I am in Silicon Valley--a giant suburb with corporate buildings.  People here are not just looking at computers/devices more, they are talking to fewer people and staying within structured work groups. Even if you work in a city like San Francisco, you’re connected to the building that you work in for most of the day—your food and your social life are there, and eventually your art is somehow incorporated into that work environment.  What's happened with our society that we can’t get out and take a drive?  What does our future look like?

People can always meet people.  Right now we don't see the result of the cyber age, the Internet and all that: the global network thing online. We are seeing how people without it are transitioning and reacting to it infiltrating their lives. It will be interesting to see how emotions are affected, and communications affected by people who were born more recently growing from birth into a society without having a reference point before mass communication and instant messaging. 

Q: With all the technology in our hands the biggest lesson we could teach our children is to get out of the house.

MATT: You’re giving them everything they need in the palm of their hand, so they don’t have to go anywhere. There’s no incentive to.  But humans always have an innate want to discover things.  People being born now might look at what we have right now and what we had before as this mythological time where people actually went out and did things. You know, "we didn’t have the Internet."  People will always rebel, at some point. They’ll rebel probably with what’s happening right now and they’ll want t to go outside, they’ll want to get back to the earth.  I mean, people are doing it right now. People want to get back to earth, get off the grid. It’s always going to be that way.  There might be more of that actually as people go into a world with complete global integration. Or provide them with the App that allows them to.

Q: It’s becoming evident that technology is basically taking all this great art and music and compressing it, controlling it, and devaluing it—and also making the exchange efficient. Yet the trustees of this art-data—what we see as art—are held to no higher standard than the kids downloading the stuff.  How can a great musician/songwriter make a living today?

MATT: All that stuff is changing.  The folks who are 15 to 25 are going into a world where they don’t have to pay for music so it’s not a thing they have to do. They’re not used it.  They’re not picking up a CD for ten bucks. That’s not the way it is. They don’t know that other way. They have no reason to feel like that’s something we should go back to. I totally get that. It’s hard to turn that back. Everyone wants something for free, let’s face it. For me and a lot of people that make music and films that can be frustrating. Originally the fans were talking, “Screw Metallica – they’re working for the man.  We don’t need to pay for their music. They have enough money.”

Today, you’re not hurting record labels [through free downloading]. If you forgot to buy a song on the Internet--for a dollar--you’re hurting the artist who’s not associated with any of that….Everybody's money will be made off merchandising and live performances. It is harder to cover costs and make any sort of stable living on the DIY level without constant touring. And you give up as much as you gain. But without the same sort of exposure on a larger scale, be it from a reputable label or some other fluke or fate it will continue to be a challenge to carve out a living. 

I think licensing happens a lot now. People get into licensing films and tv shows.  At one point people were saying, don’t sell your song out.  But now that the options are limited, it's more enticing. People are trying to find some way to navigate the system.

Money is an unfortunate reality.  At the same time I know people who download and share and give it away for free.  And that’s also what it’s about. I’d rather have my music out there for free with people enjoying it. In the end, it's all about having people hear my music and hopefully be inspired by it the way so many other artists have inspired me. I want to be a link in the ongoing chain of art and I want my link to be a strong one. 


Q: What are some bands or artists you can recommend to my readers--recent influences of yours.

MATT: For political, social commentary, Pat the Bunny is known for singing socially aware songs; Casper Allen…he’s a really good lyricist, writer. Francie Moon who I mentioned before has an incredible voice and she’s really grown as a song writer in the past year. You’re gonna hear a lot from her, check her out. Also a great underground poet/musician called, "Love The Poet" who provides a fantastic machine-gun-fire social commentary poems and spoken word. I saw her perform in Baltimore. If you want some really good politically minded folk music also check out Ryan Harvey.

Q: Do you have something you want to tell people about that’s newly available or being released in the near future?

MATT: I have some stuff I am working on that will probably be released before spring. And there’s Songs in the Key of Blue, the 7” Vinyl release that you can listen to now on Bandcamp [ ]. I am working on a book. I am always trying to work on something creative.  

Q: I think your music is really special. Thanks for spending some time...

MATT: Thank you.

Matt Pless’ latest release is in 7” Vinyl and you can hear it at . A full album called, TUMBLEWEED, was released in 2013 and has a number of timeless songs as well.  Please pay the artist for his work.

This summer, Matt Pless featured on LA indie radio station 88.9 KXLU who posted his performance on Youtube:

Matt’s Fan Site

Matt Pless Facebook Page:

Matt’s Tumbler Page:

Copyright (c) 2014, Journola. Thank you to Matt Pless for allowing us to publish his words, music, bio and likeness with attribution. Thank you to Ryan Kibby for non-exclusive, totally-revocable use of the photo.



A Link to the Past

A Link to the Past