Who's Nailin' Paylin? is an American satirical pornographic film released on November 4, 2008, that satirizes former U.S. vice-presidential candidate Sarah Palin. The film was directed by Jerome Tanner and stars Lisa Ann. Besides being a parody of Sarah Palin, the film includes spoofs of Hillary Clinton, Condoleezza Rice, Todd Palin and Bill O'Reilly.
Produced by Hustler Video, the film was shot in two days and includes five hardcore sex scenes spanning from the Paylin character's college years, home life in rural Alaska, and the 2008 U.S. Presidential election.
On October 31, 2008, Hustler announced that Lisa Ann was going to star in "Obama is Nailin' Palin?" a scene that continued on the adventures of Lisa as Sarah Palin except this time Barack Obama would be lampooned as well. The scene is only available through their Hustler members' website with no plans to release it on a DVD. This "bonus scene" was released on election eve November 3, 2008.
Hustler produced several sequels to Who's Nailin' Paylin? with Lisa Ann reprising her role, although they all used the real spelling of Palin's name- Letterman's Nailin Palin, You're Nailin' Palin (an interactive point-of-view DVD with Alexis Texas as Miss California USA Carrie Prejean), Hollywood's Nailin Palin and Who's Nailin Palin 2.