Ashmanskas has done limited film and television work, most recently appearing in the Netflix series Uncoupled.
[3][4] Ashmanskas was in the original productions of Dream (1997),[5] Songs for a New World (Off-Broadway, 1995) and the Broadway revival of Gypsy: A Musical Fable (2003).
In 2006, he played several characters in the Broadway production of Martin Short: Fame Becomes Me,[9] for which he received a Tony Award nomination, Best Performance By a Featured Actor in a Musical.
[7] He starred as the title character Off-Broadway in the New Group production of Clive at the Acorn Theatre in January 2013 through March 2013.
[16] He starred as Barry Glickman in the original Broadway production of The Prom, which opened in October 2018 at the Longacre Theatre, for which he was nominated for a 2019 Tony Award for Best Performance by an Actor in a Leading Role in a Musical.