A veteran of the Broadway stage, he began his career playing the role of Fop in the 1968 production of Cyrano de Bergerac.

He has also appeared in films such as Vanya on 42nd Street (1994) for which he was nominated for the Independent Spirit Award for Best Supporting Male, Tim Robbins's Dead Man Walking (1995), Before and After (1996), Maid in Manhattan (2002), Woody Allen's Melinda and Melinda (2004), and Wes Anderson's The Royal Tenenbaums (2001), Moonrise Kingdom (2012), The Grand Budapest Hotel (2014), and The French Dispatch (2021).

Pine began his professional acting career Off-Broadway, then in 1968 appeared as Fop in Cyrano de Bergerac at the Vivian Beaumont Theater.

[1] A founding member of the avant-garde theater company the Manhattan Project, he appeared in its 1968 production of Alice in Wonderland, directed by Andre Gregory.

as the first actor the writer encounters to have played a fictional Dave Gorman (in The Ice Storm).