Dewey Largo
He has not played a large role in the series, but was originally intended to be an uptight foil for Lisa, and her unconformist ways. In one episode, however, in which Lisa first meets Bleeding Gums Murphy, he criticizes Lisa's creative freedom with the piece he is conducting, and blatently hopes that the class won't suffer from her creativity.
In the 17th season episode "My Fair Laddy," after Willie left Springfield Elementary, the groundskeeping work was passed on to the next lowest person employed at the school, which turned out to be Dewey.
In the 17th season episode "See Homer Run," it was "visually suggested" that Waylon Smithers was caught in an act of impropriety (of a homosexual nature) with Dewey Largo and then verbally attempted to cover it up afterwards. Also in the 17th season in the episode "Homer's Paternity Coot" it is revealed that Largo was accepted to the Julliard School, but never got the letter as it was frozen atop Mount Springfield. He ended up at Springfield Elementary instead.
His last name is also an Italian word for a slow, broad musical tempo, a possible reference to the fact that he can make any piece of music uninteresting.