The first is "Wadzilla" and was directed and written by Adam Rifkin spoofing 1950s monster movies. The second segment is "I Was a Teenage Werebear" and was directed and written by Tim Sullivan which parodies Rebel Without a Cause, Grease and The Twilight Saga and is set in 1962. The third is called "The Diary of Anne Frankenstein" and was directed and written by Adam Green and spoofs Hitler and The Diary of Anne Frank. The last segment is "Zom-B-Movie", a spoof of zombie films, and was directed and written by Joe Lynch. Tying each segment of the anthology together is a framing story: a worker for the theater, in a drunken state, digs up his deceased wife's body and attempts oral sex on it, only for her to turn into a zombie and bite his genitals, causing him to slowly turn into a zombie between segments as he is working.
Adam Rifkin and Tim Sullivan met while working on Detroit Rock City and quickly discovered they shared a mutual love of horror, monster and drive-in b-movies, so they began developing an idea to make an anthology called Famous Monsters of Filmland, loosely based on the magazine they'd grown up reading, and with each short dedicated to a different era in film. First they came up with names and mock-up posters for each of the mini-features: The Diary of Anne Frankenstein (1940s), I Was a Teenage Vampire (1950s) Zombie Drive-In (1960s) and Werewolf of Alcatraz (1970s). A deal with Famous Monsters magazine fell through, so it was pitched as a weekly MTV series to be hosted by KISS frontman Gene Simmons, but reality television was beginning to dominate American airwaves, so the project was shelved.
A few years later, Rifkin and Sullivan met with directors Adam Green and Joe Lynch at Rainbow Bar and Grill, and the idea resurfaced. Soon the quartet decided to make Chillerama as an independently produced film, with Green's studio, Ariescope Pictures, serving as the headquarters of operations. 'Due to estimated budgetary constraints, Werewolf of Alcatraz was dropped and replaced with Wadzilla; I Was a Teenage Vampire was changed to Teenage Werebear at Lynch's behest; Zombie Drive-In became Zom-B-Movie; and a fifth short called Deathication was added to the drive-in sequence to fake out viewers.
"Wadzilla" is a spoof on 1950s monster movies and is about "a guy that goes to get his sperm count raised, and it creates one big sperm that attacks New York City".