The Lord of the Rings is a fantasy series created by J.R.R. Tolkien. Originally a series of books, they have been adapted into a movie series directed by Peter Jackson.

Both Tim Heidecker and Gregg Turkington are fans of the series. Gregg is much more of a fan than Tim is, self-describing himself as a “Hobbit freak,” and Bilbo Baggins as a personal hero.^[1]

The Hobbit: An Unexpected Journey was released on December 6, 2012, and was reviewed in S01E07. Gregg had been waiting for the Hobbit movies to continue the story since the end of the original Lord of the Rings trilogy, having read the original books and anticipating an adaptation. Gregg later stated it was his favorite movie of the year,^[2] and subsequently the “greatest movie ever.”^[3]

During the 1st Annual On Cinema Oscar Special, Gregg predicted that, to combat low ratings, Oscar would shock the world by revealing that An Unexpected Journey would win Best Picture, an award it was not nominated for, through a write-in vote. (It lost to Argo.) He also predicted the film would win eight Oscars in total. (It did not win any.)

Gregg felt that, despite the two Hobbit movies already planned, there would be “many, many more” movies starring Bilbo Baggins, a prediction that Tim agreed was very likely, adding that the two would be “old, gray men” and still enjoying new releases of Hobbit movies.^[4]

The Hobbit: The Desolation of Smaug was released on December 13, 2013, and was reviewed in On Cinema Christmas Special. Both reviewers loved the film, selecting it as an Oscar Pick, Gregg's only complaint being that it hadn't been released sooner. Their ratings were five bags of popcorn, with Tim giving it a bonus 5 bags, and Gregg giving it a bonus 100 bags. Gregg proposed a potential commercial in which Santa Claus was revealed to be Bilbo Baggins, calling it his “ultimate Christmas.” The movie made such an impact on Gregg that it made it difficult to focus on the other movie he was reviewing, A Madea Christmas.

During the 2nd Annual On Cinema Oscar Special, Gregg appeared wearing a Bilbo Baggins costume, complete with pipe and faux hobbit feet. He had also invited a few of his "hobbithead" friends to watch the special.

Gregg again speculated that a write-in campaign would cause The Desolation of Smaug to sweep the awards, including Best Picture, Best Actor, and Best Actress.

During the special's Oscar Behind-The-Scenes Tour, Gregg is wearing a custom made “Hobbit Head” t-shirt.