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Grudin graduated from Harvard, and earned a Ph.D. in comparative literature from the University of California, Berkeley in 1969. He received a Guggenheim Fellowship for 1992-1993. Until 1998 he was a professor of English at the University of Oregon. He has written about many political and philosophical themes including liberty, determinism, and several others.
Grudin is the author of the metafictional novel Book. He also wrote Mighty Opposites: Shakespeare and Renaissance Contrariety, The Grace of Great Things: Creativity and Innovation (finalist for the 1991 Oregon Book Award), On Dialogue: An Essay in Free Thought, Time and the Art of Living, The Most Amazing Thing, and, most recently, American Vulgar: The Politics of Manipulation Versus the Culture of Awareness.
- Mighty Opposites: Shakespeare and Renaissance Contrariety (1979) (ISBN 0-5200-3666-2)
- Time and the Art of Living (1982) (ISBN 0-0625-0355-3)
- The Grace of Great Things: Creativity and Innovation (1990) (ISBN 0-8991-9940-2)
- On Dialogue: An Essay in Free Thought (1996) (ISBN 0-8991-9940-2)
- American Vulgar: The Politics of Manipulation Versus the Culture of Awareness (2006) (ISBN 1-5937-6102-3)
- "Boccaccio's 'Decameron' and the Ciceronian Renaissance" co-authored with Michaela Paasche Grudin" (2012) (ISBN 978-0-230-34112-8)
- "Design and Truth" (2010) (ISBN 978-0-300-16140-3)
- "Robert Grudin". foresight.org. Foresight Institute. Archived from the original on September 24, 2006. Retrieved 2 April 2011.
- "Design and Truth: Robert Grudin". yale.edu. Yale University Press. Retrieved 2 April 2011.
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