Shawn's political work has invited controversy, as he often presents the audience with several contradictory points of view. Among the best-known of these are Aunt Dan and Lemon (1985) and The Designated Mourner (1997). Shawn's later plays are more overtly political, drawing parallels between his characters' psychology and the behavior of governments and social classes.

Shawn received the Obie Award for best playwrighting in 1974 for Our Late Night. In a conversation with Andre Gregory, parts of which were used to create My Dinner with Andre, Shawn said these plays depicted 'my interior life as a raging beast.' Critical response was extremely polarized: some critics hailed Shawn as a major writer, while John Simon called Marie and Bruce 'garbage' and Shawn 'one of the unsightliest actors in this city.' His 1977 play A Thought in Three Parts caused controversy in London when the production was investigated by a vice squad and attacked in Parliament after allegations of pornographic content. Shawn's early plays, such as Marie and Bruce (1978), portrayed emotional and sexual conflicts in an absurdist style, with language both lyrical and violent. He taught Latin in Manhattan, but since 1979 he has made his living primarily as an actor.

He also traveled to India as an English teacher on a Fulbright program. He studied philosophy, politics and economics, as well as Latin, at Magdalen College, Oxford, originally intending to become a diplomat. He graduated with a Bachelor of Arts in history from Harvard College. Shawn attended The Putney School, a private liberal arts high school in Putney, Vermont. He has two younger twin siblings: composer Allen Shawn, and Mary, who is autistic and lives in an institution. His parents were journalist Cecille ( née Lyon 1906–2005) and William Shawn (1907–1992), the longtime editor of The New Yorker. Shawn was born on November 12, 1943, in New York City, to a Jewish family. Haymarket Books published his books Essays (2009) and Night Thoughts (2017). He also co-wrote the screenplay for My Dinner with Andre with Andre Gregory, and scripted A Master Builder (2013), a film adaptation of the play by Henrik Ibsen, in which he also starred. His plays include the Obie Award–winning Aunt Dan and Lemon (1985), The Designated Mourner (1996) and Grasses of a Thousand Colors (2008). John Sturgis in Young Sheldon (2018–present). His television work includes recurring roles as Jeff Engels in The Cosby Show (1987–1991), Grand Nagus Zek in Star Trek: Deep Space Nine (1993–1999), Cyrus Rose in Gossip Girl (2008–2012), and Dr. He appeared in six Woody Allen films including Manhattan (1979), Radio Days (1987), and Rifkin's Festival (2020). He's also known for his roles in The Bostonians (1984), Prick Up Your Ears (1987), Vanya on 42nd Street (1994), The Double (2013), Maggie's Plan (2015), and Marriage Story (2019). He also voiced Rex in the Toy Story franchise (1995–2019). He is best known for his film roles in My Dinner with Andre (1981), The Princess Bride (1987), and Clueless (1995). Wallace Michael Shawn (born November 12, 1943) is an American actor, playwright, and essayist.

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