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A Hard Sell: Eclectic Singer-Songwriter Nat Osborn Makes Albums for the iPod Generation 

For some people, playing a gig at the Bitter End, the historic New York area rock club located in Greenwich Village, might be a sign that perhaps they had finally made it. But singer/songwriter Nat Osborn, who was celebrating his 18th birthday at the time that he first played a show there, had a different reaction. With a hearty laugh, he recalls his reaction was simply, "Why aren't we playing a bigger venue?"

As it often goes, success wouldn't come overnight. But nearly a decade later, Osborn is right where he wants to be. He's the namesake behind the Nat Osborn Band, a sprawling seven-piece horn-infused project that brings together myriad musical styles, from the reggae-tinged sounds of "Yours Alone" to the Randy Newman-esque "Little to the Left," a song which Osborn describes as "a tune about hipster girls."

In a recent phone conversation from his Brooklyn home, Osborn spoke about the long road that he took to find his way musically to what he's doing now with the Nat Osborn Band. He went to a liberal arts college for four years and continued to play gigs, coming back to New York to play shows while also traveling to Boston as well as other colleges to play additional shows. After college, he moved to Brooklyn and that's when he says he really became, in his view, a professional musician. Of course as he allows, the real journey and fight to realize his own dreams was just beginning.

"It's a hard thing to juggle doing your own project and paying rent," he says. "So I've definitely spent a lot of time playing on other people's projects, doing film score work, composing for dance companies, bartending — you know, whatever I need to do. But for the last couple of years, I've been really lucky. I've been mostly able to focus on the Nat Osborn Band. I've watched that project grow and grow. I think that all of those experiences, every single one, has informed who I am now and allowed me to be the leader of the Nat Osborn Band. I wouldn't have been ready for this role a couple of years ago."

Osborn admits that cutting his teeth in the highly competitive New York City music scene was both challenging and necessary. Valuable time would be spent navigating an arduous path which would further strengthen his resolve and leave him better equipped as an artist to kill on the road, something that tied in with an important realization.

"I think that all of us, everyone has kind of realized that you've got to cut your teeth in New York, because New York is where you're going to realize how good you've got to be. Any night you go out, you're going to see bands who are incredible, original and exciting, working super-hard. [They] have their stage show, look, brand and everything together. Those guys might play to 60 people in New York. Then if they go out on the road and they're cultivating a following outside of town, they're really going to stand out outside of New York."

After releasing The King and the Clown in 2013, Osborn and the band hit the road and toured extensively, including a successful jaunt playing a number of overseas dates. As he says, they've now sold music on nearly every continent that human beings live on — there are no sales in Antarctica yet, but they're working on it.

The diversity on The King and the Clown reflects the restless nature of Osborn's creative songwriting mind, one that never has any fear in exploring a different direction, even if it makes it difficult to reconcile within the final product.

"It was hard," he says. "We were conscious that we definitely wanted to make an album that was cohesive. But I do write in a ton of different styles, so we wanted to make sure that certain sounds and voices were constant throughout. Certainly the horns helped that and using some of the same keyboards. That was kind of key to giving the album a cohesive sound. But I also wanted it to be a bit of a journey and I wanted it to be eclectic. I get bored when I hear the same song done in a different way over and over. I think that most of my generation does."

It's a sign of the times and Osborn did his best to meld the listening habits of the current crop of music fans with his own preferences.

"Most people who are under 30 grew up with an iPod in their pocket and are used to being able to flip between songs," he says. "We're far more used to that than we are putting on a record and listening to it top to bottom — which is something that I like to do and I was conscious of wanting to make a record that I felt could do that. But I also wanted to make a record that was eclectic and diverse and had a trajectory throughout to keep you interested but [also] took you a bunch of different places."

After playing at this year's installment of South by Southwest, Osborn and his band come to Cleveland for a show at the Winchester Music Hall as part of a three-week tour. The Cleveland show will feature material from a new EP that's currently in the works and Osborn says that the latest songs really came to life on the stage.

"A lot of it happened organically, just from being on the road and seeing what songs we were taking to and playing night after night," he says. "Which songs were growing and augmenting and shifting and which songs were kind of feeling stale. I would introduce new songs and we would kind of shape them — because we didn't have a lot of time and we'd be on the road and I'd want to introduce a song — we'd have one rehearsal and then they'd really kind of come together onstage."

As a result, the new songs are more defined by how they've been played live.

"The other songs were definitely more conceptual and then put together in the studio and then adapted for the stage," he says. "I think that because of that, they're high energy and it's interesting — we're working the opposite way that we did with the first record. So now we're taking songs that we've been doing live and figuring out how to adapt them to the studio and how to shape them, what to add and what to take away. I'm really excited about it."

The Nat Osborn Band, 9 p.m. Friday, March 21, The Winchester, 12112 Madison Ave., 216-226-5681. Tickets: $10, thewinchester.net.

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