In 1981, Winfield joined writer-performer Adam Long and actor Daniel Singer to found the Reduced Shakespeare Company, a collective dedicated to the writing and performing of Shakespearean parodies.
After departing from The Reduced Shakespeare Company, Winfield served as a writer for the Daytime Emmy Award-winning series Teacher's Pet (starring Nathan Lane and Jerry Stiller).
Winfield is the author of What Would Shakespeare Do (Ulysses Press, 2000), a self-help book that employs Shakespearean drama as a basis for advice.
The work uses a historically plausible story of William Shakespeare's young adulthood in conjunction with a comic modern plot to explore themes of religious persecution, authorial intent, and human sexuality.
It has been stated that the modern portion of the novel's plot has been based, in part, on Winfield's years studying Shakespeare in Santa Cruz and Berkeley.