Hest's father is a college music professor and his mother a cantor. His older brother, Daniel, is Hest's former manager. Hest took piano lessons as a child and later taught himself to play guitar. Hest attended Cornell University in Ithaca, NY beginning in 1999 and later transferred to New York University, where he received a degree in Communications in 2002.
Hest released an EP, Incomplete and two albums, Come Home and Story After Story. In March 2004, Hest signed a recording contract with Columbia and recorded the album Someone To Tell and a five-song EP "Guilty Hearts EP" in the fall of 2005. His next album was called The Green Room Sessions and he worked with producer Mitchell Froom on the follow up album called "The Break-In". In 2009, he released Twelve Mondays, a collection of 12 fan-selected songs reworked and rerecorded. In 2011, Hest released his fifth album, Sunset Over Hope Street. He released his sixth album, The Fire Plays in 2012. Hest recorded music videos for his songs "They're On To Me" (2004), "So Slow", and "Dead End Driving".