Benny the Assassin first appeared in the review of Princess Diaries 2: Royal Engagement as the assassin for hired by Hyper Fangirl so that the Nostalgia Critic would be forced to review the Princess Diaries 2 with her. At the end of the episode after Hyper is blown into space, him and the Critic vow to change gender stereotypes as seen in the Princess Diaries 2.
During the review of Christmas Story 2, Benny meets up with Hyper again as she tries to cheer up the Critic.
During the review of Spawn, Benny is contacted by the Critic to be hired by Satan to serve as his new hitman. He impresses the lord when kills his would-be assassin and shows off his aim for the devil.
During the review of Old vs. New: Cinderella, Benny clashes with Devil Boner over who is Hyper's number 1 hitman until they become friends upon learning they love the same movie in Ever After and end up watching the movie together in the end alongside Hyper and the Critic.
During the review Old vs. New: Evil Dead Benny is called in by the Critic to protect him from Hyper Fan Girl and Devil Boner only to join in on the breakdown of what made the movies so unique.
Benny makes a came in the review of Alvin and the Chipmunks: Chipwrecked where he serves as the Best Man for Devil Boner and Hyper Fan Girl's wedding.
Benny appears in the review of Doom where he, the Critic, Devil Boner, and Hyper all try to enjoy a game supposedly based on the movie which was based on the game; only to find it sucked like the movie and then join forces to destroy everything related to it, Benny obliterating the movie's script.
- Princess Diaries 2: Royal Engagement (2014)
- Christmas Story 2 (2014)
- Spawn (2016)
- Old vs. New: Cinderella (2016)
- Old vs. New: Evil Dead (2017)
- It is revealed in Old vs. New: Evil Dead, that the character Bill is his brother.
- Satan respects Benny as shown in Spawn and Alvin and the Chipmunks: Chipwrecked, and also considering the fact that they are both played by Malcolm Ray.
- Benny since his first appearance has become good friends with the Nostalgia Critic, Hyper Fangirl, and Devil Boner.