Born Margaret Wander, Dessa’s first release with Doomtree, False Hopes, introduced a unique sensibility to underground hip-hop: literary, bitter-sweet, and wry. She alternated between a clever, droll persona as an emcee and her earnest, unaffected delivery as a singer with a low, clear alto voice. Her a cappella arrangements delicate and expressive, full of sad, old world harmonies. False Hopes attracted a varied set of ferociously dedicated fans in the Midwest and beyond.