Jesse Montgomery III is a fictional character appearing in the 2000 film Dude, Where's My Car?. He is portrayed by Ashton Kutcher. Jesse is one of the two main characters of the film alongside his best friend and roommate, Chester. The two of them got so wasted the previous night that they can't remember anything, which becomes a problem when they discover the morning after that Jesse's car is missing. While searching around town trying to retrace their steps as to where the car ended up, Jesse and Chester stumble upon a host of crazy characters. He's in a relationship with Wanda, a woman who lives with her fraternal twin, Wilma. The latter of which just so happens to be in a relationship with Chester. However, there's also a strong possibility that Jesse had a sexual encounter with Christie Boner in the back seat of his car during the night that he was completely wasted.