Heald has worked extensively on Broadway and has been twice nominated for the Tony Award for his work as Lord Evelyn Oakleigh in Anything Goes (1988) and Terrence McNally's Love! Valour! Compassion! (1995). He also appeared in McNally's The Lisbon Traviata (1989), Inherit the Wind (1998), Deep Rising (1998), and Lips Together, Teeth Apart (1991).
He made brief appearances in Miami Vice ("The Prodigal Son"), X-Men: The Last Stand (2006 film), and the Cheers series finale "One for the Road". He later appeared on the Cheers spin-off Frasier in a recurring role. He appeared in Unaccompanied Minors as a distressed, Christmas-hating airport employee.
Heald lives in Ashland, Oregon with his wife Robin and children Zoe and Dylan. He has converted to Judaism, his wife's faith. He regularly performs in productions of the Oregon Shakespeare Festival. During the 2010 season of the Oregon Shakespeare Festival, Heald played Shylock in Shakespeare's The Merchant of Venice.
