May Erlewine was born to a musical family; her father Michael Erlewine was a member of the Michigan blues band The Prime Movers and founded the online music guide AllMusic while her uncle is a luthier.

[1] According to Mark Deming, her work shows a variety of musical influences, such as folk, bluegrass, blues, rock & roll and others.

It grew from her experience as a child, home-schooled and surrounded by music, and as a teenager, when she hitch-hiked across North America, riding freight trains and performing on the streets.

The song, "Shine On" was covered by Rani Arbo and Daisy Mayhem on their 2007 album Big Old Life and by Sawyer Fredericks in the final round of The Voice in 2015.

[5] In late 2018, Erlewine played a series of collaborative shows with fellow singer-songwriters Sav Buist and Katie Larson (both from The Accidentals) and Beth Nielsen Chapman.