Born and raised in Oklahoma, Boland grew up listening to a mix of country and rock and roll before eventually finding himself at the epicenter of the Red Dirt scene in Stillwater, where he put together the Stragglers while attending OSU. The New York Times called Boland “one of the country scene’s most multidimensional songwriters,” while American Songwriter praised him as “a troubadour for the ages,” and Rolling Stone hailed him as a “steady, reliable source of smart, gritty songwriting”.

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