Fay Wolf will make you cry. And it’ll feel really really good.

Originally from Connecticut, Fay Wolf is an L.A.-based singer-songwriter who refers to her live performances as “sadsongfunnyjokemusictimes.” On their own, her songs beg comparisons to Tori Amos, Joni Mitchell and Ani Difranco.

In 2009, Fay Wolf released Blankets, her debut EP. Following the release, Fay’s music spread via word-of-mouth, and fans regularly gather to see her perform at venues like Hotel Café in Los Angeles and...