Captain Feathersword is a friendly pirate captain who owns The S.S Feathersword, and is Wags the Dog's best friend and owner. He was portrayed by Anthony Field and his two brothers, Paul and John. Then in late 1995, Paul Paddick became Captain Feathersword after understudying for Anthony in a concert when he had an operation and he has played him ever since. On occasions, Paddick's understudies would fill in his roles, such as in newer episodes of the Dorothy the Dinosaur series. Although his role was originally minor, it became so significant that he is often called the Fifth Wiggle.
Captain Feathersword also has a crew, The Friendly Pirate Crew, all of which idolise and have the same bright and cheerful personality as their captain.