DeWilde signed a two-picture deal with Disney in 1964. He first starred in "The Tenderfoot", a three-part comedy Western for Walt Disney's "Wonderful World of Color" TV show with Brian Keith. The following year he and Keith did "Those Calloways" for theatrical release, reuniting deWilde with his "Good-bye, My Lady" star Walter Brennan. Also in 1965, deWilde played a young PT boat officer, Esn. Jere Torry, the estranged son serving under his US Navy Admiral father played by John Wayne in the Pacific theater WWII drama, "In Harm's Way" (1965).