Born in Milwaukee, this musician became fascinated with the trombone at an early age. But a different world opened up to him upon finding a battered acoustic guitar in his married sister's room. Taking the guitar to a local music shop, Elsesser was given some tuning tips and, within three months, was performing at his high school. After graduating from the University of Wisconsin, he moved out to San Francisco, becoming a bartender when not playing shows in and around the area at open-mic nights. He also performed with Delmarva and MK Ultra at this time. In 1997, Elsesser relocated to New York City where he began performing at legendary venues like the Knitting Factory and the Mercury Lounge. In 2000, he went to Nashville to record his debut album, simply titled Henry, which was released in 2001. He has performed at various festivals including the Montreux Atlanta Music Festival. He is often cited for his singer/songwriter style and pop sensibilities along the lines of Elvis Costello and Dave Matthews.
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