The second son of Joseph F. H. "Pro Joe" Cutrona, an Army general and combat veteran (Silver Star), he was a native of West Point and spent much of his early life in a military setting.
He had larger supporting roles in the 1996 action film The Glimmer Man and the 1999 thriller Deterrence while continuing to make frequent guest appearances in all genres of TV shows.
He satirized his military roles in a TV commercial for the KAYAK travel site and showed up in sitcoms like Becker and in crime dramas like Brooklyn South.
He collaborated with Joe Frank on his Peabody Award-winning series' on National Public Radio produced by KCRW: Work in Progress, Somewhere Out There, In The Dark, The Other Side and Unfictional from 1987 until 2016.
Samuel Beckett granted him rights to perform three theatrical solo premieres of his prose texts All Strange Away at La MaMa.