Pierson appeared with George C. Scott on Broadway in Tricks Of The Trade, before continuing on to do several New York soap operas and many regional theater plays. Some notable theatrical roles include Angelo in Measure For Measure at the Yale Rep, Stanley in A Streetcar Named Desire at the Penn Ctr. Stage, Bobby in Speed The Plough at the Philadelphia Theatre Company, and Ricky in Glengarry Glen Ross and Teach in American Buffalo at the Virginia Stage Company. His most prominent daytime role was as Frank Ryan on Ryan's Hope, a role he played from February 1983 through September 1985.
Pierson's first high-profile prime-time television role was as Jack Malloy, the head of a dysfunctional family, in The WB sitcom Unhappily Ever After, which was created by Ron Leavitt, one of the creators of FOX's Married... with Children. Other TV roles include a leading role as R.T. Howard on That 80's Show, and recurring roles on Grace Under Fire, In Plain Sight (USA) and The Firm (NBC). He also had a recurring role as Rodney's long lost dad on the ABC comedy Rodney.
In 2005 and 2006 he appeared in two episodes of Veronica Mars as Stewart Manning, the father of Meg Manning. In 2006, he guest-starred in Criminal Minds, playing Max Ryan, a former FBI agent-turned-author and Jason Gideon's mentor who comes out of his retirement to capture a serial killer known as the Keystone Killer in the episode, "Unfinished Business". From 2006 to 2013, he portrayed Miami-Dade Police Captain Tom Matthews on the Showtime series Dexter.

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