Keaton Simons is proof positive that pain can be, well, beautiful.

Consider the inspiration for his sophomore album, "Beautiful Pain." The Hotel Cafe stalwart was playing a festival in upstate New York a few years ago when happenstance brought him together with the woman who would soon be his girlfriend. The experience was so powerful that it inspired the haunting songs on the album.

"I made it a point early on in my career to open myself up, to expose my vulnerabilities when I record," he said. "I'm the same way when I perform. I just love the idea of getting out there with a guitar and singing what I feel."

Simons comes from a family that is well steeped in entertainment, though he veered from television and movies toward music when he was quite young. His earliest music idols were the Beatles, Joni Mitchell, Ray Charles and Sam Cooke.

Keaton Simons with Jason Adamo and Andrew Tufano
» Where: Jammin' Java, 227 Maple Ave. East, Vienna
» When: 6:30 p.m. doors, 7:30 p.m. show Sunday
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"It was something that came to be naturally when I was very, very young," he said. "My mom played piano, and I watched [and soon joined in]. I am just lucky that I have a family that understands."

His family also helped Simons hone his music. That's resulted in not just a notable solo career but collaborations with a host of artists including Gnarls Barkley, Snoop Lion (back when he was Snoop Dog), Josh Kelley and others.

This latest album, co-produced by Mikal Blue (Colbie Caillat, One Republic), includes co-writes with some of his musical friends including Jason Mraz, Jason Reeves and Toad the Wet Sprocket's Glenn Phillips.

But for all his high-profile musical partnerships, one listen underscores that Simons' music is entirely personal. That's why it took him a few years to finish the songs on this latest release -- he wanted the romance to fully develop so he could tell the whole story in song (Simons and his girlfriend, publicist Laura Goldfarb, are now happily based in Los Angeles).

Now, as Simons confronts the "Beautiful Pain" of moving ahead in music, he remains positive that will also have the happiest of endings.

"Believe me, if I didn't know better, I'd be discouraged. I am close personal friends with extremely successful artists that were dropped or dumped and then came back and made it," he said. "I'm going to keep writing and writing and performing and performing. I'm going all the way with this."