The Long Trails and Tall Tales of Matt Pless

For years, I’ve wanted songwriter and modern-day troubadour Matt Pless to sit long enough to answer some questions about traveling and performing music. The Baltimore-based artist has done plenty of both over the last several years. He estimates he’s played 800 shows or more since 2013. He’s been adding to the tally recently with a new tour that sweeps through Texas this month, including a stops in Houston for a Sunday evening set at Walter’s.

It’s not just Pless’s determination to take his music to the masses that interests me. As someone who’s followed his career since his stellar 2013 release, Tumbleweed, I’ve also followed the stories associated with him. The music is wonderful, but the folk tales are borderline legendary and involve names like Prince and Katy Perry. Pless treats these tales – which he claims are all true – like his songs. That is to say, he fuels them with fascinating, wordy detail.

Before we get to the tall tales and long trails, I ask Pless what he recalls about his trips to Houston.

“Houston, I remember, being filled with enthusiastic kids who loved DIY culture and independent bands. First time I played here I got housed up with a girl who had a killer flu and I ended up sick as a dog for a week,” he recalls, then goes on to proclaim his love for Whataburger and Houston sunsets. “Houston is way cooler than a lot of places, I'd say.”

That’s quite an endorsement considering all the pins Pless has already poked into his travel map. Before he hit the road, he was a city kid from Maryland, a self-proclaimed “fast-talking, sarcastic, East Coast smartass.” He remembers writing his first songs as a third-grader, tunes he and a friend sang to classmates during recess. Those were the origins of a showman who’s honed his skills over thousands of hours of shows.

“I’ve never been nervous or anxious onstage. I've been performing in various forms since I was a child, school plays and homemade movies and such, so it's kinda just a part of who I am I guess," Pless recalls. "My first show was with my old pop-punk band at our high-school talent show.

"I remember walking out and being blinded by the spotlight. I couldn't hear anything, we were playing in that huge auditorium full of people screaming and cheering obnoxiously. I just hit the first guitar chords, started singing amidst that wild blur of noisy, static chaos and thought to myself, ‘I am gonna do this for the rest of my life.’”

He’s tried to honor that promise with prolific writing and traveling. He says he’s been around the U.S. 18 times playing music, virtually nonstop since 2013. That’s when I first met him, at a 4/20 music fest in southeast Houston. Pless has met thousands of people since then, I’m sure. But, he correctly recalls I bought him a beer that night because he was one of a handful who’d heard of my son’s band, Days N Daze, back then.

I’m nowhere near the most notable character he’s met while touring.

“Strangest character I ever met on the road was this old man in Tennessee who sat in a folding chair under an umbrella on the sidewalk of a busy intersection every day, preaching about the end times through the mouth of a ventriloquist dummy he kept on his lap,” Pless relates. “He had a bullhorn and a speaker system and all these signs about fire and brimstone and all that. He was ranting about how he used to be a trucker until the night his dummy came to life and told him he had to spread the warning of the coming apocalypse, in the same fashion as Noah warned of the flood. He hasn't made it in a Matt Pless song, but I did put him on one of my older album covers.”

What about his oddest gig?

“One time, in 2008, I somehow ended up playing at a Christian camp in Michigan. After my set, a preacher started screaming to the audience about how Obama was the Antichrist and how rock music was the sound of the devil,” he says. “One time, I was playing a coffee shop in Austin to a crowd of seven people when Jack White walked in the back door and stood there watching my set until I recognized him and sorta took a double-take from the stage. He left after that. Next day, on the Internet, I found out he got arrested later that evening in a bar fight.”

The biggest gig he recalls was at City Winery in New York City for the release of Occupy This Album, an Occupy Wall Street benefit album. Pless’s track, “Something’s Got to Give,” is the lead song on a compilation that also includes Jackson Browne, Willie Nelson, Patti Smith, Debbie Harry and others.

“I got too wasted after my set, got called up for an encore, forgot the words to one of my songs and stopped midway through, in front of 600 people. I really screwed up, in front of the media, celebrities and other high- profile people. Bruce Willis was there! You can ask him about it.”


There’s a line in “Call It Art,” one of Pless’s newer songs, that imagines his pursuits leaving him dead, “broke and lonely and unknown.” It’s a rumination on art and how fame is always near, but just out of Pless's reach.

“I worked as a stagehand for a while," he relates. "One time I was on as a ‘runner’ for a Prince show. I had to run out and get things for bands — food, props, drugs, magazines, etc. Prince wanted a boombox, a half-hour before the show, or else he wouldn't go on stage. One of his people gave me 800 bucks and sent me off to find the boombox. I brought it back, gave it to one of the people on the tour crew, Prince went on stage, and played a great show. But I dunno what he did with the boombox.”

Is it true that Katy Perry stole your record deal, I ask?

“Yes, in a way, Katy Perry did indeed steal my record deal," he confirms. "Back in 2006, 2007. The story involves a millionaire freemason who found me playing music in the NYC subway, gave me $1,400 in cash, shopped my demo, got me to the door of Island Records, told me I had to wear a cowboy hat and stop writing politically charged music. I didn't play ball.

"The VP of Island was putting most of his budget into a ‘new artist he signed named Katy,’ according to my freemason middleman," Pless continues. "So, due to lack of funding into my project, and probably lack of a cowboy hat, Katy Perry got the gold. But, ultimately, it shoulda been me playing the Super Bowl and dating John Mayer.”

Tell me one more, I insist. The James Franco story.

‘Yes, I was in NYC crashing on my friends’ couch and while wandering around one afternoon, I saw a long line. It turned out to be a magical line and I got to audition for the HBO series The Deuce, which stars James Franco. They thought I had ‘cool hair,’ so they gave me a part as an extra.”

These might seem like tall tales. They happened, Pless says, but that’s not the point. The point is he would never have been in a position to have these moments if not for the music and the places it’s taken him. He sings with a clear voice that’s all his own, but there are hints of Bob Dylan and Paul Simon there. When Pless is served alphabet soup, it's a sure bet he sees more letters than broth in his bowl because he fills up songs with lyrics from beginning to end, to the glee of anyone listening for poetic content that runs from thoughtful to droll. His latest single, a scathing political commentary titled, "When the Frayed Wind Blows," contains more than 600 hundred words, all matched to fit across and down like a musical crossword.

Of his last release, 2016’s Lavender, Pless says, “I wrote the whole thing on acid. It was really different than my usual style. Okay Recordings are going to re-release it on vinyl soon and change the title to Call It Art. You can lick 20 limited edition copies of the jacket and talk to God through a backward message. I have a new album out right now called Catch Me If Ya Can. I didn't write it on acid. It's got a good deal of political and socially-themed songs on it. I think people will dig it.”

So Pless travels on, content to create new stories in new and revisited places. Next stop, Houston, Texas.

“Touring that much is amazing, but like anything in excess, it can eventually fuck you up in many ways,” he says. “I've never toured outside the country except for Canada and one time a rich supermodel took me on a cruise to Mexico. I want to hit up Europe in 2018, though. That's always been a dream of mine.

“This current tour is gonna roll through at least half of the summer,” Pless adds. “When it's over I am going to chill out and work on finishing a memoir, doing regional shows, looking to branch my audience beyond the DIY scene, getting famous, making a million dollars and seeing what happens next.”

Matt Pless performs Sunday, May 21 at Walter's Downtown, 1120 Naylor, with Days N Daze, Noogy, Dead Rabbits, Radio Flyer and Metanoia. Doors at 8 p.m., all ages, $7.