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. In 1987, the Company presented The Complete Works of William Shakespeare , which became an international hit and, eventually, the longest running comedy production in London's West End, where it was nominated for a Laurence Olivier Award for Best New Comedy in 1997. The Complete Works of William Shakespeare (Abridged) Returns to Original West End Home | london.broadway.com. He contributed to the editing and adapting of The Complete Works for publication Amazon.com: The Complete Works Of William Shakespeare (Abridged) - Acting Edition: Jess Winfield, Adam Long, Daniel Singer: Books and television performance. The Complete Works of William Shakespeare (Abridged) (2000) (TV) - Full cast and crew.

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), as well as for the animated features Stitch! The Movie and Leroy and Stitch for Disney.

Jess Winfield was originally born Jess Borgeson, and changed his name to Winfield in 1993 after marrying his wife, Sandra Thomson... his works prior to 1993 are known under this former name. 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. In 2008, he published the novel My Name Is Will (Twelve/Hachette Book Group, 2008). 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. Jess Winfield - About