- Son of William Shawn, the legendary editor of The New Yorker.
- As a child, staged musical puppet shows with his brother, Allen, for their parents and friends.
- Before breaking into acting, taught drama and Latin at the Trevor Day School in New York City.
- Our Late Night, the first play he wrote that was produced, was initially booed by off-Broadway audiences but went on to win the Obie award in 1975; he also won Obies for 1986's Aunt Dan and Lemon and 1990's The Fever.
- First appeared on stage was in the 1977 production of his translation of Niccolo Machiavelli's The Mandrake.
- Big-screen debut was in Woody Allen's romantic comedy Manhattan (1979); his best-known film role, in Rob Reiner's The Princess Bride, followed in 1987.
- Has appeared on numerous TV series, including The Cosby Show, Murphy Brown, Star Trek: Deep Space Nine and Gossip Girl.
- Benjamin W. Chon — Grandfather
- William Shawn — Father
- Deborah Eisenberg — Significant Other
- Allen Shawn — Brother
- Cecille Shawn — Mother
- Harvard University, Cambridge, Massachusetts, United States (BA in History); attended University of Oxford, Magdalen College, Oxford, England