The movie opens with spoofing "Armageddon" and "10,000 B.C." In the year 10,001 B.C., a caveman Will (Matt Lanter) runs away from a mammoth before getting in a fight with Wolf (Ike Barinholtz). He then encounters a saber-toothed, gasoline-drinking Amy Winehouse (Nicole Parker), who informs him that the world will end on August 29, 2008 (which was the film's opening day and Michael Jackson's 50th birthday), revealing their fate laying in a crystal skull "Indiana Jones". The film flash-forwards to the present, where Will apparently dreamed all of this. He then finds out that his girlfriend, Amy (Vanessa Minnillo), is having an affair with Flavor Flav (Abe Spigner) and the two break up with Will not admitting his true feelings for her.
Later that day, Will has a "Sweet Sixteen" party at his house, despite the fact that he's 25. Among the guests are Juney (Crista Flanagan) spoof of "Juno" and Will's best friend Calvin (Gary "G-Thang" Johnson), who attempts to curve a bullet around the room "Wanted" to stop Seth and McLover "Superbad" (Noah Harpster and Austin Scott) from stealing the alcohol, accidentally killing "Dr. Phil" (John Di Domenico), Anton Chigurh (Barinholtz), and the Beautiful Assassin (Carmen Electra) in the process. By then, Amy arrives with her new boyfriend, an underwear model (Nick Steele), before the "High School Musical" number is performed with cameos by an off-key Jessica Simpson (Parker) and Justin Timberlake (Jonas Neal)..