Clohessy was born in the Bronx, New York, the son of John Clohessy, a police officer. He fought in the 1975 Golden Gloves in Madison Square Garden. He graduated from Pearl River High School in Pearl River, New York, and from SUNY Purchase where he studied under Walt Witcover.
Clohessy has had recurring roles in daytime dramas All My Children, Boy Meets World, and Guiding Light. In primetime, he has become known for his multiple regular turns as police officers and other law enforcement officials, creating parallels between his acting career and upbringing by his policeman father. The first of such roles was in the seventh and final season of Hill Street Blues, as Officer Patrick Flaherty. The following season, Clohessy was cast as the new co-star of Pat Morita on the ABC detective series Ohara, playing Lt. George Shaver. In 1995, he appeared in the episode "Hell's Angel" of the situation comedy Double Rush.
He later joined the cast of the HBO prison drama Oz as Correctional Officer Sean Murphy. However, in between these roles, Clohessy had a supporting role as Thomas Smaraldo on NBC's comedy/drama Tattingers (1988–89) and soon after appeared in a starring role on NBC's short-lived comedy One of the Boys (1989). Clohessy co-starred on the Neal Marlens/Carol Black ABC sitcom Laurie Hill in 1992, playing a stay-at-home freelance writer. In 2008, Clohessy had a regular role in the short-lived Fox show New Amsterdam. He won a Screen Actors Guild Award for Best Ensemble in the HBO series Boardwalk Empire.

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