Terlesky was born in Cincinnati, Ohio, on May 30, 1961. Since the mid-1980s, Terlesky has acted in a number of films and television series. His first notable television role was in the NBC drama Legmen. His other television credits include The Facts of Life, V, Our House, Empty Nest, Walker, Texas Ranger, a recurring role on Guns of Paradise and co-starring in the sitcom The Last Frontier.

Some of Terlesky's film acting credits include Secret Admirer (1985), The Naked Cage (1986), Chopping Mall (1986), Valet Girls (1987), The Allnighter (1987), Deathstalker II (1987), Appointment with Death (1988), Damned River (1989) and Crazy People (1990).

In 1998, Terlesky made his directorial debut with the film The Pandora Project, co-directing with Jim Wynorski. He directed a number of other independent, direct-to-video and television films before getting involved in episodic television. Since 2006, he has directed episodes of Boston Legal, Grey's Anatomy, Ugly Betty, Drop Dead Diva, Human Target, Army Wives, Body of Proof, Gossip Girl, Castle, Agents of S.H.I.E.L.D., How To Get Away With Murder, and The Blacklist (TV series).