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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). He worked extensively for Disney's Lilo & Stitch franchise, writing the animated features Stitch! The Movie and Leroy & Stitch (also serving as a dialogue director), executive producing Lilo & Stitch: The Series, and voicing Jumba Jookiba in the English versions of Stitch! and Stitch & Ai. His role as the official voice actor of the character became firmly established in 2018 after the death of the character's original voice actor David Ogden Stiers. He has also written scripts for several other television series such as Mickey Mouse Works, All-New Dennis the Menace, House of Mouse, The Penguins of Madagascar, The Legend of Tarzan, Buzz Lightyear of Star Command, 101 Dalmatians: The Series, The Savage Dragon, The Incredible Hulk and Hercules.

Jess Winfield was 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.

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 (Abridged), 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. He contributed to the editing and adapting of The Complete Works for publication and television performance.

Jess Winfield (born March 8, 1961) is an American novelist, self-help author, television writer, and voice actor who is a founding member of The Reduced Shakespeare Company. His books include: What Would Shakespeare Do (2000) and My Name Is Will (2008). He wrote for and served as an executive producer of a number of animated television series, including Teacher's Pet and Lilo & Stitch: The Series. He is also the official voice actor for Jumba Jookiba in the latter series' franchise since 2009, voicing the character in the English versions of the anime Stitch! and the Chinese animated series Stitch & Ai.