Family Guy (1999)

S4E2 Fast Times at Buddy Cianci Jr. High

Brian takes on the role of a substitute teacher at Chris' school after Chris' regular teacher hits the jackpot in the lottery. Assigned to a class filled with troubled students, Brian finds himself in a unique situation. Meanwhile, Chris develops a crush on his new teacher, Mrs. Lockhart, who cryptically tells him she will only love him if he eliminates her husband. Upon discovering this unsettling arrangement, Lois and Stewie conspire to show Chris that he needs to rethink his choices.