Thomas Kemper plays “Man of Constant Sorrow” as his dog, Oswald, sings along | Video and photos: Stephanie McGeary


If you’ve spent much time in Old Town, you’ve surely encountered a few buskers – folks singing or playing music for passers-by, in the hopes of receiving some monetary donations. But how often have you encountered a busking dog? Well, if you’ve been in Old Town recently, probably at least once.

His name is Oswald Cobblepot, the Associate (yes, like the Penguin from Batman, but with “the Associate” at the end) – a seven-year-old German shepherd and American bulldog mix, who can often be heard loudly howling along with the booming voice and guitar strumming of his partner, Thomas Kemper, near the Old Town Gazebo.

The duo, usually bearing a sign that reads “veteran and his dog sing for tips” have drawn the interest of many listeners, some who have wonder how this adorable canine learned how to sing. Kemper said that one day his furry friend just started singing along with him, completely out of the blue.

“Somebody asked me one day ‘how long did it take you to teach your dog to sing with you?’” Kemper told the Outpost, sitting outside Old Town Coffee and Chocolates Wednesday morning. “And I said ‘I didn’t.” He did it spontaneously…Then I thought, why don’t I make it a part of my act?”

Since Kemper first brought home his pal as a 14-week-old puppy, Cobblepot didn’t so much as make a peep for most of his life. He never barked at other dogs. He never howled along with the sound of ambulance sirens. “I actually thought he was a barkless dog,” Kemper told the Outpost.

Then about two years ago, Kemper said, he sprayed on some new cologne and, seemingly offended by the smell, Cobblepot barked at his owner for the first time. Shortly after that he started vocally expressing himself regularly, howling along with many of Kemper’s songs.

At first, Kemper said, he thought his dog was howling out of pain or dislike of the music. But after some time, it became clear that his pup was enjoying himself. Cobblepot seems to join in when Kemper hits a certain tone with his singing – the right combo of volume and pitch just seems to set him off. “Then once he gets rolling he just does what he feels, joining in at different parts,” Kemper said. 

Unlike his canine partner, 54-year-old Kemper has been singing pretty much his whole life. He grew up in a very musical family – his dad was a jazz saxophonist and his mom was a classical pianist. Kemper said that his parents, who were very into the Human Potential Movement of the 1960s, would set up a radio in his room when he was little and keep it on all the time, changing the station daily, to expose him to different musical styles. Apparently it worked, because he has always loved music and started singing when he was very young. He got his first guitar when he was 14 and taught himself to play to accompany himself. He’s been busking ever since.

Kemper said that he used to have a much wider vocal range – nearly four octaves. But a little more than seven years ago, Kemper was in a pretty serious motorcycle accident that left him with several injuries, including to his vocal cords. He was able to find his singing chops again, but he now stays in the bass range. What Kemper lacks in vocal range, he more than makes up for in volume and soul, belting out sounds that seem to resonate across all of Old Town. Kemper draws a lot of his inspiration from other singers who don’t necessarily have a lot of range, but do have a unique style, even some grit, to their voice – like Billie Holiday, Tom Waits and Bob Dylan.

“I would rather hear somebody who doesn’t necessarily have the technical virtuosity and capacity, but who has the soul,” Kemper said. “I’d much prefer somebody who just plays their heart out.”

Working as a busker, Kemper has spent most of his life traveling and has lived all around California, Arizona, Texas and Oregon. After most recently living in Eugene for a stint, Kemper and Cobblepot came down to Humboldt last November and are currently living at Nation’s Finest, a transitional housing facility for veterans in Eureka. Kemper is a veteran, having served in the Navy in the 1980s. 

Throughout his travels Kemper has had many different living situations — living out of an RV, camping — and has often been without conventional housing. But he’s never considered himself homeless, and identifies as “an urban backpacker” he said. He is currently seeking permanent housing, with support from Nation’s Finest. Kemper said he’s seeking a little more stability for himself and especially for his old pal, Cobblepot, who is getting older.

In case it isn’t apparent by this point in the story, Kemper really loves Cobblepot, who has been faithfully by his side for seven years. All of Kemper’s family has passed on, he said, and Cobblepot really is his only family, as well as his best friend and musical partner. He also is a real crowd-pleaser and when Cobblepot isn’t singing, he is usually eagerly approaching people, his butt wiggling excitedly, asking for love and pets.

“Oswald is such a social butterfly,” Kemper told the Outpost. “He really loves people. He’s taught me to be way more tolerant of people.  He’s got unconditional love. So he’s teaching me more of that.”