Drew Kennedy

Anderson Fair presents Drew Kennedy.

Rebellion doesn’t have to be loud. Smarter won’t always get in your face. A revolution can be an awfully nice guy with a small Bose p.a. and head full of songs in a Prius, passing 15-passenger vans and tour buses on his way to his next gig.

“You can’t wait for someone to give you the green light,” says Drew Kennedy, his Prius parked in his New Braunfels, Texas, driveway. “You have to take ownership over what you’re doing and make it happen for yourself. If you wait for someone, you’re going to be waiting for a long time. Maybe forever.”

Over the past decade, Kennedy has left the waiting to other people. The 35-year-old has devoted his life to writing and performing his songs his way for anyone who cares. With a catalog seven-albums deep, one novel penned, a music festival created, and an ever-growing group of admirers comprising elite peers and everyday listeners, Kennedy has done more than build a strong career in music. He has reimagined what it means to be a contemporary songwriter, both artistically and entrepreneurially.

But tell that to the guy himself, and he shrugs and smiles.

“I just want to write the best songs that I possibly can,” Kennedy says. “I don’t want to ever stop approaching this as a student of popular song or the craft of writing.”

His most recent release, 2014’s Sad Songs Happily Played, is both a career-spanning snapshot and a winning testament to his instinctive “well, why not?” M.O. On a Friday night in November 2013, Kennedy performed in one of his favorite venues, a former post office in League City, just southeast of Houston. Talking to the sound engineer after the show, he mentioned what an ideal space it’d be for a live recording.

That’s when the engineer told him he already had the whole evening on tape.

The night so serendipitously captured on Sad Songs is token Kennedy: his distinct but regionally muddled drawl, formed by a youth in the Northeast, college in the South, and adulthood in the Southwest, yokes beautifully crafted, often heartbreaking songs with side-splittingly funny stories in a seamless give-and-take. As the show rolls on, you can almost hear his audience leaning in, held captive by the guy on stage with just a guitar.

“I’ve always been attracted to more somber music,” Kennedy continues. “But I like making people laugh, too. I like knowing I can keep them engaged for two hours. I look at all of it as an extension of songwriting — making the arc of the show go from beginning to end and giving a reason why you’re playing each song.”

Kennedy was 19 when he decided he wanted to give the guitar a try. His grandfather bankrolled his first steps. “He gave me 300 bucks and I went out and bought a black acoustic Yamaha guitar that was $299,” he says. “I started gigging within a month of getting that guitar. And it was awful. But I didn’t know any better.”

Kennedy chocks his willingness to jump first, ask questions later to naiveté, and that’s probably true, at least during his earliest years on stage. But another motive has overwhelmingly helped him call the shots: he likes proving people wrong. “I was supposed to be a lawyer or something,” he says. “I was supposed to do what everyone else does: find a safe job and make a bunch of money and be successful that way. I want to show people that you don’t have to do that to be successful — to be the kind of person that you want to be.”

Today, Kennedy’s definition of success is simple and unyielding. “I just want to serve the inspiration that will become the song and make it as good as I possibly can,” he says. “And that is it.”

Fidelity to inspiration defines just about everything Kennedy does, including deciding when to record. He released his first album, Hillbilly Pilgrim, in 2003, and the dozen years since then have seen a steady flow of output: 2007’s Dollar Theatre Movie; 2010’s An Audio Guide to Cross Country Travel and live offering Alone, But Not Lonely; 2011’s Fresh Water in the Salton Sea, best savored with its companion novel of the same name — Kennedy’s first and only work of prose to date; 2013’s Wide Listener; and 2014’s Sad Songs Happily Played.

Kennedy’s collections have earned widespread attention. No Depression, Engine 145, CMT Edge and other beacon roots publications have heaped praise upon praise of his efforts. His always expanding circle of co-writers and collaborators now includes Lori McKenna, Walt Wilkins, Matraca Berg, Jeff Hanna, Travis Meadows, Susan Gibson, and other heavy hitters, while Jason Boland and the Stragglers, Patty Loveless and Jason Eady, Bart Crow, and more have recorded his work. McKenna and Kennedy’s richly layered story song “Rose of Jericho” made its way onto both of the writers’ most recent studio albums.

Kennedy makes regular trips to Nashville, every month and a half or so. He still marvels at the immensity and ingenuity of the town’s creative community, and he approaches co-writing as a learning opportunity that doesn’t end once the session’s over. “You take a little bit of every co-writer you have with you. The next time that you’re sitting by yourself and writing a song and you feel an urge to say it one way, you think, ‘Well, what’s another perspective?’” He concludes, “The more I surround myself with these incredibly poetic voices, the more it improves my own in my own songs.”

The Red River Songwriters’ Festival is another Kennedy creation designed to provide heavy doses of inspiration in numerous forms, from the landscape and devoted fans from all walks of life, to the brilliant artists who perform. Launched in 2011 by Kennedy and a Red River local he calls a “patron saint of songwriters,” the baby festival has now drawn some of roots music’s premier voices: Jeff Hanna, Matraca Berg, Lori McKenna, Ray Wylie Hubbard, Bruce Robison, and others have all made the trip, joining red-letter core group Walt Wilkins, Susan Gibson, Kelley Mickwee, Josh Grider, Brandy Zdan, and of course, Kennedy.

Reflecting on his chosen line of work and dogged insistence on doing things his way, Kennedy is grateful. “I appreciate that it’s not a ‘hard good,’” he says. “I’m not inventing a longer lasting light bulb. They’re songs. Songs can impact people in a very personal way, but it’s not like groceries and clothing — it’s an emotional need, not a physical need. I’m very aware of the fact that I’m really lucky to get to do this.”

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