Whitmore first released albums on Southern Records and later on ANTI-. His act consists mostly of playing the banjo or guitar while singing, though on occasion he performs a cappella. While he has earned much acclaim from the folk, blues and alt-country communities he is also rooted in the hardcore punk community, for example by playing on a homage to Bad Religion.
Whitmore has toured with Chris Cornell, City and Colour, Murder by Death, Clutch, Lucero, Converge, Red Sparowes, Modern Life is War, Frontier Ruckus, Frank Turner, Esmé Patterson and The Low Anthem.
Whitmore"s 2009 release, Animals in the Dark, reached Number 50 on the Billboard Heatseekers chart.