Jaymay was born on January 3, 1981, and was raised on Long Island. After graduating from New College of Florida in 2003, she was unable to find a job in book publishing and moved back to New York to play professionally.

She has been described by the BBC as being the "darling of the New York 'Anti-Folk' scene", and by the New York Times as a "big name...for the indie universe".

Jaymay appeared on the TV-show Late Night with Conan O'Brien on Monday, April 1, 2008 and on The Late Late Show with Craig Ferguson on Tuesday, May 13, 2008. She also appeared on In the Colored Room, on Channel 5, on May 17, 2008.

She has collaborated with Kevin Devine on the songs "Brother's Blood", "Time to Burn" and "Murphy's Song", with Cheyenne on "Write It Down in Red", and with Dirty on Purpose on "Light Pollution, Like Bees". In 2010, it was announced she would provide guest vocals on art-metal band Goes Cube's second full-length studio album, In Tides And Drifts. She is also featured on the My Cousin, The Emperor's songs "Burly, Old Couch" and "Somedays" from "The Subway EPs, Vol. I: Prospect Park West" released March 29, 2011.