7 Comedians Who Completely Botched Their Transition to Film

3. Jamie Kennedy

There was a brief moment in time where it seemed Jamie Kennedy would become a household name sheerly from the force of his likeable nature. Oh, how times can change. Somewhere between his breakthrough role in Scream and his starring role in Malibu's Most Wanted, Kennedy found a way to make people hate him. Hard. Once the dorky wiseass that everyone wanted to grab a beer with, he soon transformed every character he played into a pompous, proudly infantile dummy. He used his roles in Malibu's Most Wanted and Kickin' It Old Skool to trot out every cliche about black culture he could dig up, severely dating his movies in the process. Later, his attempt to fill Jim Carey's shoes in Son Of The Mask cemented the fact that this once effortlessly charming comedic actor was now, unfortunately, only reminding audiences of how funny he used to be.