After amassing a fervent live following, Jeffrey Gaines landed a record deal in the early '90s, which resulted in three critically-acclaimed albums. In 2001, his cover of Peter Gabriel's "In Your Eyes" became an Adult Contemporary hit. Jeffrey Gaines most recently performed at the Outpost as part of an "Artists in the Round" in May 2014, along with Richard Barone, Deni Bonet, and Milton.
A gifted songwriter whose lyrics paint sometimes witty, often poignant portraits of characters often unaware of how their lives have gone wrong, Freedy Johnston seemingly appeared out of nowhere in the early ’90s and quickly established himself as one of the most acclaimed new singer/songwriters of the day. Rolling Stone named him Songwriter of the Year in 1995, with his 1994 album "This Perfect World" being the impetus for that distinction. His latest album, "Neon Repairman," was released earlier this year. American Songwriter states: "He (Johnston) tells you a story that seems so damned entertaining. But when it’s over, despite being impressed, you feel like you’ve just been worked over by one of the greats. And you have."