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He made his theatre debut in 1975, starring opposite Meryl Streep in the revival of the comic play Trelawny of the "Wells" at The Public Theatre's Shakespeare Festival. He played Che in the first Broadway production of Andrew Lloyd Webber's Evita (1979), earning a Tony Award for Best Featured Actor in a Musical, as well as the roles of Georges Seurat/George in Stephen Sondheim's Sunday in the Park with George (1984) for which he was nominated for the Tony Award for Best Actor in a Musical. He portrayed Lord Archibald Craven in the original Broadway cast of Lucy Simon's The Secret Garden (1991). On Broadway, he replaced Michael Rupert as Marvin in William Finn's Falsettos (1993). He starred as Burrs in The Wild Party (2000) and earned a second nomination for the Tony Award for Best Actor in a Musical.

He had leading roles in television shows, playing Dr. Jeffrey Geiger in Chicago Hope (1994–2000); SSA Jason Gideon in the CBS crime-drama series Criminal Minds (2005–2007); Saul Berenson in the Showtime drama series Homeland (2011–2020); and Rufus Cotesworth in the Hulu mystery series Death and Other Details (2024). He earned seven Primetime Emmy Award nominations for his television work, winning Outstanding Leading Actor in a Drama Series for Chicago Hope in 1995. He had recurring roles in Dead Like Me (2003–2004,) and The Good Fight (2021).

He also had film roles portraying Inigo Montoya in Rob Reiner's family adventure film The Princess Bride (1987) and Avigdor in Barbra Streisand's musical epic Yentl (1983), for which he earned a Golden Globe Award for Best Actor in a Motion Picture Musical or Comedy nomination. Other film credits include Ragtime (1981); Maxie (1985); Dick Tracy (1990); True Colors (1991); Impromptu (1991); Wonder (2017); and Life Itself (2018). He also voiced roles in Hayao Miyazaki's Castle in the Sky (2003) and The Wind Rises (2013).