The original concept was just a parody of the opening jungle trek and temple scene from Raiders of the Lost Ark. The project was put on You tube for fun but was quickly noticed by Jimmy Buffett's Media Director. The crew was contacted about showing a five minute trailer during a Jimmy Buffett concert on 08/12/2006 and it was during the intermission in front of 19,900 people. The film makers met Buffett and he told them that he wanted to make a cameo, something they have been pursing to this day.
The entire opening sequence was shot three times over a period of twelve years due to changes in the story and people leaving the project. Each time the scene was shot the sets got bigger and the production became much more involved. The opening sequence includes over fifty extras, a seaplane, pirates, horses, and multiple indoor and outdoor constructed sets.
The film makers own one of the yellow barrels used in the making of the movie JAWS. The yellow barrel is featured in every scene of the web series as a running gag. There are also multiple references to the film including a line spoken by Dr. Marcus Denny where he uses the phrase, "swallowed up whole".
All of the exterior scenes in the web series that are supposed take place in Cancun are actually shot in a sand and gravel pit in New Hampshire. The location was used for multiple days including the famous Desert Chase from Raiders of the Lost Ark where Indy is dragged under and behind a truck. In the Adventures of Indiana James a custom school bus designed to look like a pirate ship was used instead of a truck. The school bus, called The Buffett Bus, was designed and operated by two brothers Chris Hoff and Howie "CHIP" Hoff. Director Thomas Pimentel met the Hoff brothers in the parking lot of a Buffett concert in 2006.
Most of the cast thought making Indiana James was a total waste of time. The lingering production process and constant re-shoots left many of the cast members frustrated and disenfranchised. Many new characters, endless re writes and brand new scenes were added to make the ridiculous plot make any sense at all.