Heald grew up on New York's Long Island to Iceland in Massapequa Park.
After finishing school Heald graduated from Michigan State University. During his studies, which he finished in 1971, he had his first appearances in a theater group. During the next 15 years he worked mainly in the theater. After appearances on Broadway, he was nominated for the Tony Award twice, once for his role in the play Love! Valour! Compassion! and for his appearance in the musical Anything Goes.
From the early 1980s, Heald has also worked as an actor in movies and on television, where he first took over mostly small supporting roles. A wider audience, he was known Silence of the Lambs in the film in the role of the Institute Director Dr. Frederick Chilton. From 2000, he took over one of the main roles of the series Boston Public producer David E. Kelley. He played there the easy choleric deputy principal Scott Guber.
In 2002 he took over in Red Dragon, a prequel to The Silence of the Lambs, again the role of Dr. Chilton. Due to the success in the role of the prison director and Hannibal Lecter - opponent Heald was increasingly set to roles as shady villain (see type casting ). The permanent role offers bored him increasingly. He did not always play " the scum in the suit ." So he turned away again in 2007 reinforced the theater in order to be able to play more varied roles.
In 2008 he took over the role of being the leader in Thornton Wilder's play Our Town. The following year he played the William Shagspeare in Bill Cain's play equivocation. As part of the Oregon Shakespeare Festival Heald took over in 2010 the role of the Jewish moneylender Shylock in Shakespeare's The Merchant of Venice.
Besides his work as an actor Heald is also active as a spokesperson for the production of audio books.
After years in New York and Los Angeles Heald moved in 1996 with his family to rural Oregon. He lives there with his wife Robin Herskowitz Heald - town Ashland. The couple has a daughter and a son.