Doug Walker has stated that his original concept for the anniversary special was an adventure story called Ninjas vs. Pirates, in which the Channel Awesome bad guys (Dr. Insano, Dark Nella, Mechakara, etc), would go on a quest to steal a magic medallion that holds secret powers, and the Nostalgia Critic and his team would be trained by Black Dog Bill (Walker) to be pirates. The Nostalgia Critic's costume would resemble Captain Jack Sparrow from the Pirates of the Caribbean films. Ultimately, the story would lead to the resurrection of Bloodbeard Joe, a supernatural being mentioned quite often by Black Dog Bill in the How to Be a Pirate series. Walker wanted his good friend James Rolfe of AVGN fame to play Bloodbeard, but unfortunately Rolfe was unable to appear due to a very busy schedule. As a result, Walker decided to scrap the project and go with his Suburban Knights fantasy epic, in which Rolfe has a voice-over cameo.
According to Doug Walker, The Nostalgia Critic's gauntlets for his Link costume were made from a pair of brown socks with the fingers cut out. Walker bought them from a young boy at a comic convention.
First appearance of James Jarosz, who would later go on to be a recurring character actor on the series as well as a "jack-of-all-trades" behind the scenes.