Paul Newman had been approached about the project in 1984 but turned it down due to not having done much comedy work before although he liked the film and encouraged the Coens to go ahead without him. The Coens instead waited ten years until he agreed to do it.
This is one of the few Coen brothers movies to not be edited by the brothers themselves (under the pseudonym Roderick Jaynes) along with Tricia Cooke. Thom Noble was the editor here.
Jennifer Jason Leigh won the role of Amy Archer over Ellen Barkin, Nicole Kidman, Winona Ryder, and Bridget Fonda.
Sam Raimi: in the Hula Hoop manufacturing sequence as one of the Hudsucker brainstormers. We don't see his face, only his silhouette and we hear his voice.
Joel Coen, Ethan Coen: [Gunderson] Two consecutive films made by the Coen Brothers feature the character name Gunderson. In The Hudsucker Proxy (1994), the elevator operator is named Clarence "Buzz" Gunderson (as seen in a newspaper headline). In Fargo (1996), one of the main characters is Police Chief Marge Gunderson.