<Li> Constance "Connie" Brooks (Eve Arden) is an English teacher at fictional Madison High School . </Li> <Li> Osgood Conklin (Gale Gordon) is the blustery, gruff, crooked, and unsympathetic principal of Madison High, a near - constant pain to his faculty and students . (Conklin was played by Joseph Forte in the show's first episode; Gordon succeeded him for the rest of the series' run .) Occasionally, Conklin would rig competitions at the school--such as that for prom queen--so that his daughter Harriet would win . </Li> <Li> Philip Boynton (Jeff Chandler on radio, billed sometimes under his birth name Ira Grossel; Robert Rockwell on both radio and television), is a Madison High biology teacher, the shy and often clueless object of Miss Brooks' affections . </Li> <Li> Walter Denton (Richard Crenna, billed at the time as Dick Crenna), is a Madison High student, well - intentioned and clumsy, with a nasally high, cracking voice, which he can disguise when making mischief, often driving Miss Brooks (his self - professed favorite teacher) to school in a broken - down jalopy . Perfectly aware of Miss Brooks' feelings, he tirelessly tries to help her snare Mr. Boynton, despite the latter's cluelessness . </Li>

Who played mr boynton on our miss brooks