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Wilkinson trained at the Royal Academy of Dramatic Art before making his West End debut portraying Horatio in Hamlet (1980) for which he received a nomination for the Laurence Olivier Award for Best Actor in a Supporting Role. He returned to the West End playing Dr. Stockmann in the Henrik Ibsen play An Enemy of the People (1988) receiving a Laurence Olivier Award for Actor of the Year in a Revival nomination.

Wilkinson received the BAFTA Award for Best Actor in a Supporting Role for The Full Monty (1997) as well as two Academy Award nominations, one for Best Actor for In the Bedroom (2001) and Best Supporting Actor for Michael Clayton (2007). He became known as a character actor, acting in numerous films such as In the Name of the Father (1993), Sense and Sensibility (1995), Shakespeare in Love (1998), The Patriot (2000), Girl with a Pearl Earring (2003), Eternal Sunshine of the Spotless Mind (2004), Batman Begins (2005), Valkyrie (2008), The Ghost Writer (2010), The Best Exotic Marigold Hotel (2011), Belle (2013), Selma (2014), The Grand Budapest Hotel (2014), and Denial (2016).

In 2009 he won a Golden Globe Award and a Primetime Emmy Award for Outstanding Supporting Actor in a Miniseries or a Movie for playing Benjamin Franklin in the HBO limited series John Adams (2008). His other Emmy-nominated roles were as Roy/Ruth Applewood in the HBO film Normal (2003), James Baker in the HBO film Recount (2008), and Joseph P. Kennedy Sr. in the limited series The Kennedys (2011).