In 1990, Vess began one of his best-known collaborations to date, with writer Neil Gaiman. He illustrated "The Land of Summer's Twilight", one of the four episodes in the original "The Books of Magic" mini-series, and worked on three issues of Gaiman’s critically acclaimed "The Sandman" series. "Sandman" #19 ("A Midsummer Night's Dream") is a meta-fictional adaptation of William Shakespeare's play and in 1991, that issue won the World Fantasy Award for Best Short Story, the only comic book to hold the honor, as award organizers subsequently amended the rules to specifically exclude comics. Vess contributed eight drawings for a prose-based inset that appeared in "Sandman" #62 ("") and illustrated the final issue of the series, "Sandman" #75, a second Shakespeare adaptation ("The Tempest"). He drew the covers for the "Books of Faerie" spin-off series "Molly's Story" (1999).