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Gallagher was born in Wilmington, Delaware, and was raised there with his two older sisters. His parents, John and June Gallagher, are folk musicians. He attended Brandywine High School. He eventually went on to play in numerous bands, including Not Now Murray, What Now, Annie's Autograph, and Old Springs Pike. Gallagher played Tom Sawyer as a child actor at the Delaware Children's Theatre.
Before and throughout his Spring Awakening run, he was in the folk-rock group Old Springs Pike. On January 23, 2008, his fellow band members announced his departure. The next day, Gallagher made an official announcement confirming his departure on his MySpace page. Old Springs Pike later officially changed their name to the Spring Standards