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Born in Honolulu and raised in Pittsburgh, Jennings’ musical journey began with a move to Minneapolis in the late 1990s, where he released his debut album and quickly gained attention for his raw, authentic sound. His contemporary take on classic folk resonated with listeners and fellow musicians alike, earning him fans like Jack Johnson and Isaac Brock of Modest Mouse. Over the years, his steady output of albums has solidified his reputation as one of the leading voices in the folk and Americana scenes.