Set somewhere in the seventeen years between the events portrayed in The Shaggy Dog and The Shaggy D.A., the film follows the adventures of Wilby Daniels, now a successful lawyer, who has proposed marriage to his girlfriend, Betty. However, an aged Professor Plumcutt passes away and his last words are that his infamous enchanted Borgia Ring that transforms people into Old English Sheepdogs is to be inherited by Wilby, which again sets another sheepdog transformation in progress when Professor Plumcutt's evil, bumbling caretakers seek it for themselves. Wilby's younger brother, Moochie, now an adult, comes to his aid when the curse reactivates, and Wilby agrees to help him in exchange by getting cast as the perfect dog for a dog food commercial, as Moochie is a struggling casting director. Together, they must once again break the Borgia curse before Wilby's wedding to Betty, but this time by Wilby carrying out Professor Plumcutt's last wish to take ownership of the cursed ring and thus put an end to dog transformations.
It marks the end of the original story with Wilby as the son of Wilson and Freida Daniels.
It was featured on The Wonderful World of Disney, being preceded by the 1959 film, The Shaggy Dog. In keeping with the tradition that Walt Disney introduced films, it was introduced by Disney CEO Michael Eisner, who attempts to invoke the transformation on Wilby, but when Eisner states the words, he has passed on the curse from Wilby to himself.
Even though Wilby was the older brother to Moochie, Gary Kroeger is two years younger than Todd Waring.