Cory Pendergast played the role of Jimmy Leach - who is the class clown, always trying to entertain everyone in the room. Aside from being the class clown, Jimmy is also Mr. Lombardo's star sailing pupil, which places him in a situation where he has to trade boat labor in order to get free lessons. During the movie, Sam gives Jimmy advice about how to become "a real boatman," which of course, Jimmy appreciates.
After his role as Jimmy Leach, Cory went on to have a pretty decent career for himself. He appeared briefly in "There's Something About Mary" (in which Matt Dillon also had a role), and then went on to star in the movie "18," together with co-stars Toi Svane Stepp (Nicole), Dee Wallace and Joyce DeWitt. For some reason, the film's negative (the original copy) had mysteriously disappeared, which is why the movie never got released. Today he does various commercials for Netflix, National Car Rental and Macy's.