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Born in Wisconsin, Dennis got a large part of his early musical education as a child in Germany, when "every day I'd come home from school and turn on the Armed Forces Radio Network (AFN). Most of the DJs were regular GIs who'd brought their record collections overseas. A lot of the music was from the south and they'd play a lot of rhythm and blues and a lot of country music. Back then the armed forces were one of the most integrated parts of society, and that was reflected in what the DJs played. It was all just music - not black music, not white music – and most of it was somewhat out of date, since there wasn't the emphasis on constantly playing the current top 10 hits of the time."

After returning to the United States, Dennis attended high school in Maryland. He soon bought a brand new Martin D-18 and began writing songs. "It's still the guitar I write 'em on," he says. Dennis spent the 70s and 80s traveling around the West and Midwest, including Kansas, Colorado, Nevada, California, Oregon, Montana, Minnesota, and North Dakota, playing in coffee houses and bars, writing songs, and working odd jobs. When he reached Austin, Texas, Dennis performed both as a solo act and with a band. Next stop was Washington, DC, in the mid-80s, where he formed his own band. He did an occasional solo gig, such as opening for Steve Earle at the Birchmere. Then, for most of the '90s, he got out of music altogether.

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