Bashoff was born in Philadelphia, Pennsylvania, the son of Irene (Zalcman) and Kenneth "Ken" Bashoff. His family is Jewish. Bashoff started acting at the age of 10, working primarily in commercials, and then singing and dancing in film and theater. He moved to Hollywood after graduating from Washington Preparatory High School in 1999.
Bashoff had a role in the CW hit show One Tree Hill in its first season. He also appeared in Bushwhacked, Big Bully (for which he won a Young Artist Award), and The New Swiss Family Robinson in 1998. After taking a break from acting, he received a recurring role on Judging Amy, playing the character of Eric Black, an abused gay teenager. In 2000, he played the role of Jesse in You're Invited to Mary-Kate and Ashley's School Dance Party. He has since appeared in Deuces Wild and Minority Report, and has a minor recurring role in One Tree Hill. He also appeared in an episode of Charmed, "The Bare Witch Project", as Duncan, a young man who accidentally conjured Lady Godiva. Then he plays the role of Josh Cooper, a victim's son, in the seventh episode of season four in the series NCIS. In October 2006, he landed a recurring role as Karl in the television series Lost, both in the third and fourth season.
On December 18, 2007, Bashoff made his Broadway debut in the role of Moritz Stiefel in the Tony Award-winning musical Spring Awakening, replacing John Gallagher Jr. His last Broadway performance was on August 2, 2008. He was replaced on Broadway by former ensemble member and Moritz understudy Gerard Canonico. Bashoff reprised his role as Moritz on the first national tour of Spring Awakening. He ended his run with the Spring Awakening national touring cast on August 16, 2009, and was replaced by Taylor Trensch.

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