Noble teachers are a movie staple, but this unusual, realistic film, although a bit formulaic, surprises us with its skilled, dedicated, flawed educator. As one who asks hard questions, and presented as a great teacher, he also twice lets a well-connected student cheat. Privately telling the cheater that he himself is flawed, he rightly adds, "I failed you."

William Hundert (Kline) is retiring after 34 years of teaching classics at St. Benedictus, a private East Coast school for boys. Its students are the sons of the rich, and the school's mission is to mold them into leaders. Hundert has always said, "A man's character is his fate," and asks his students, "How will history remember you?"

A U.S. senator (Yulin) has a troubled son there, and insists, "You, Sir, won't mold my son! I will." The smart-aleck student, Sedgewick Bell (Hirsch), interrupted class, chided the teacher, and kept a cache of men's magazines, booze, condoms, and cigarettes. The other students idolized him, as the young consider an older man who wants them to think and do well silly, and that nothing is cooler than a defiant peer.

Hundert, a bachelor quietly in love with the wife of another faculty member, Elizabeth (Davidtz), had to accept her goodbye. He redoubled his work, each year holding a "Mr. Julius Caesar" quiz show in which the three best students competed. Sedgewick at last applied himself, due to paternal threats, improving enough to finish fourth. Hundert, wanting to reward him, maybe also finding rebels more interesting than bookworms, took a second look at Sedgewick's paper, raised his grade, and made him a finalist. If that had been so the first time, Hundert wouldn't have had to review Sedgewick's fourth-place paper. He got to competd in the contest, but cheated, which Hundert saw and found a silent way to block.

A few years later, Sedgewick is a rich man planning to run for senator, ready to give a huge gift to St. Benedictus, on the condition it re-run the Julius Caesar contest. The viewer can decide if he redeems himself. An eventual confrontation between Sedgewick and his own son is profound. Hundert, aware that he neither let Sedgewick win nor exposed him, thus faces his ethical shortcomings, and subtly sees justice done. As Hundert, Kline offers a character better than most teachers and most men. We care for him because he regrets so much that he's imperfect.