One movie has won an MTV award in two separate years
This is a weird one owed to MTV's propensity to drop random categories in there from time to time. (Best Sandwich in a Movie, anyone?) I suppose as a way of gauging interest in the summer movie season that laid ahead in June of 2007, they had a bizarre category called "Best Summer Movie You Haven't Seen Yet." But in all likelihood it was just a way to bolster business for the upcoming "Transformers," which was released by Paramount (a Viacom stablemate of MTV's). The film even dominated the pre-show ad space with a big Shia LaBeouf interview and various materials. It was back one year later to win the award for Best Movie at the 2008 MTV Movie Awards, making it the only film to take a prize in two separate years. Incidentally, those are the only two MTV Movie Awards a "Transformers" film has ever won.