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Bad Teacher: Hollywood's Best Worst Teachers From Ferris Bueller to Sam Kinison

How rotten is Cameron Diaz's “Bad Teacher?” From Sam Kinison to Jon Stewart, the big screen's bad apples.

Gemma LaMana

Principal Richard Vernon – The Breakfast Club

John Hughes’ seminal 1985 teen drama follows five high schoolers from different cliques—the brain, the athlete, the princess, the criminal, and the basket case—who spend a Saturday in detention together in the school library. Their power-tripping, comically mean-spirited principal, Richard Vernon (Paul Gleason), orders them not to speak or move from their seats, and instructs them to each write an essay about “who you think you are.” Vernon treats his students with nothing but disdain, verbally haranguing them every chance he gets. In one infamous altercation, he assigns the rebellious Bender (Judd Nelson)—whom he particularly despises—two months of detention for talking back. Vernon ultimately locks Bender in a storage closet and, in a moment of weakness, physically threatens him. And, in one of the few scenes that really lets us inside Vernon’s psyche, he complains to the custodian about how the students have changed. “No, you’ve changed,” replies the custodian.

Dan Dunne – Half Nelson

In one of the best film performances of the decade, Ryan Gosling stars as Dan Dunne, a twentysomething idealistic middle-school teacher in Brooklyn who eschews the school curriculum in favor of dialectics. Dan does an admirable job of reaching students by teaching them how to interpret historicity, and helps give each of them a powerful analytical voice. However, we soon learn that Dan is addicted to crack cocaine when one of his players on the girls basketball team he coaches finds him getting high in a bathroom stall. Dan strikes up an odd friendship with the girl, but as he spirals deeper into addiction, he begins showing up to class hung over, and grows more cynical about his ability to shape his students’ minds. During the 2006 film’s climax, he even orders crack to be delivered to him at a seedy motel by the aforementioned girl.

Mr. Hand – Fast Times at Ridgemont High

Jeff Spicoli (Sean Penn, in his 1982 breakout performance) wanders through the halls of the fictional Ridgemont High School in a marijuana-induced haze, living up to his personal mantra: “All I need are some tasty waves, a cool buzz, and I’m fine.” Killing his buzz, however, is the school’s no-nonsense American history teacher, Mr. Hand (Ray Walston). When Spicoli wanders into class late on the first day of school, with a semi-valid excuse that he couldn’t locate the classroom, Mr. Hand proceeds to rip up his schedule in front of the entire class, and tells him to take a hike. Later, when Spicoli orders a pizza to be delivered to the classroom, Mr. Hand lets the entire class consume the pie in front of a crestfallen Spicoli. On the evening of the graduation dance, Mr. Hand shows up to the surfer dude’s home and, surmising that Spicoli has wasted about eight hours of classroom time over the school year, treats him to a marathon tutoring session. “You dick!”

Dolores Umbridge – Harry Potter and the Order of the Phoenix

Gone is the cutesy back-alley abortionist that melted hearts in Vera Drake. In the Harry Potter films, Imelda Staunton plays Dolores Umbridge, the strict Defence Against the Dark Arts teacher who is a plant from the corrupt Ministry of Magic. Umbridge refuses to teach the children practical magic, forcing Harry Potter (Daniel Radcliffe) and Co. to form a secret group, dubbed Dumbledore’s Army, to train in defensive spells. In the 2007 sequel, the Slytherin students are then recruited by Umbridge to uncover the group, and she eventually achieves her objective after illegally dosing Harry’s love interest, Cho Chang, with Veritaserum. After she wrestles power away from Dumbledore at Hogwarts, Umbridge appoints herself headmistress, and makes life hell for all the students there—even attempting to stop Harry and Co. from aiding Sirius Black after Harry has a vision of him being tortured. With all due respect to Severus Snape, Umbridge is the most reviled teacher at Hogwarts.

Professor Dave Jennings – Animal House

Faber College’s Dean Wormer may be one mean son of a bitch, but most of the sanctions he places on the rowdy Delta Tau Chi House (see: double-secret probation) are pretty warranted in this 1978 classic. They do kill a horse in his office, after all. Professor Dave Jennings, a disenchanted English teacher played by Donald Sutherland, has far less scruples. When he’s not busy lecturing his students on radical politics, he’s smoking up with them—including a hilariously awkward scene where Delta frat brothers Pinto (Tom Hulce), Boon (Peter Riegert), and his girlfriend, Katy (Karen Allen), share a few joints with Professor Jennings. Later, Boon discovers that Katy has been having an affair with Jennings when he catches the professor at her place wearing only a cardigan (exposing his butt).

Professor Terguson – Back to School

Thornton Melon (Rodney Dangerfield) is a self-made apparel mogul who owns a chain of Tall and Fat stores—providing clothes for plus-size people. After he splits from his cheating, gold-digging wife, he visits his son (Keith Gordon) in college and learns that he and his friend (Robert Downey Jr.) are social outcasts on campus. In an effort to reconnect with his son, and help realize his son’s dream of joining the school diving team, Thornton bribes his way into the college (despite never graduating high school). In this 1986 comedy, while he succeeds in striking up a romantic relationship with his fetching literature professor, he’s also forced to go toe-to-toe with the school’s certifiably insane history teacher, Professor Terguson—a Vietnam War veteran played by the late Sam Kinison, who is prone to violent outbursts in class when his students share their liberal viewpoints.

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Dean Edward R. Rooney – Ferris Bueller’s Day Off

Few filmmakers possessed a greater disdain for authority than the late John Hughes, who became the voice of a generation of disillusioned teens in the 1980s. In addition to The Breakfast Club’s Dean Vernon, Ferris Bueller’s Day Off’s Dean Rooney (Jeffrey Jones) also became a cultural symbol of authoritarianism gone haywire. Aside from Ferris’ sister, Jeanie (Jennifer Grey), Dean Rooney is the only one who suspects high school senior Ferris Bueller (Matthew Broderick) of truancy. When Ferris fakes a cold to get out of class and goes on a wild weekday adventure, Dean Rooney loses it, and searches all over town for Ferris. Eventually, Dean Rooney resorts to breaking into Ferris’ family’s home, only to find Jeanie there, who kicks him in the face, and the Bueller’s family dog, who does far worse.

Jim McAllister – Election

In a brilliant example of full-circle casting, filmmaker Alexander Payne chose Ferris Bueller himself, Matthew Broderick, to play Jim McAllister, a bored Nebraska high school teacher who runs the school’s student government. His nemesis is Tracy Flick (Reese Witherspoon), a brownnosing overachiever who on the surface appears to be a goody two shoes student, but in reality hides a lascivious side—one that got Jim’s best friend, a fellow teacher named Dave, fired when she had an affair with him. Jim hasn’t forgotten, so when Tracy decides to run for student body president, he rigs the election in favor of Paul Metzler (Chris Klein), a dimwitted football player who’s popular among the students, by disposing of two of Tracy’s votes. When the school janitor exposes his deception, Jim resigns from his job, and his wife also divorces him after she discovers that he tried to organize a motel sex rendezvous with his best friend Dave’s ex-wife, Linda.

Professor Furlong – The Faculty

In Robert Rodriguez’s 1998 sci-fi tribute to Invasion of the Body Snatchers, the faculty of Herrington High School is taken over by parasitic aliens who control their every move. A motley crew of students, including the campus drug dealer (Josh Hartnett), the school jock (Shawn Hatosy), his popular girlfriend (Jordana Brewster), a nerdy photographer (Elijah Wood), an edgy outcast (Clea DuVall), and the new girl (Laura Harris), must band together to stop the teachers from infecting the entire student body and transforming them into aliens. The first teacher they take on is the science teacher, Professor Furlong, played by The Daily Show’s Jon Stewart. When they confront him, he attacks the students and nearly strangles the nerd to death before the dealer intervenes, slicing off his fingers with a paper cutter, and then stabbing him in the eye with his own personal drug that he pushes around campus, killing the alien. Since the aliens require excessive water, the drug, a diuretic, turns out to be the alien’s weakness.

Mr. Strickland – Back to the Future

In Robert Zemeckis’ first Back to the Future film, Marty McFly (Michael J. Fox) plays a 17-year-old high-school student who accidentally travels back in time from 1985 to his father’s senior year of 1955, thanks to a sports car-time machine, the DeLorean, built by the oddball scientist “Doc” Brown (Christopher Lloyd). In an Oedipal twist, Marty accidentally causes his mother to fall in love with him, and is forced to unite his father and mother, lest he create a paradox that would nullify his very existence. Mr. Strickland (James Tolkan), is the bald, strict, disciplinarian principal of Hill Valley High—which both Marty and his father attended—and hates all matter of “slackers,” including Marty and his father. He often taunts young Marty in the school hallways, at one point saying, “I noticed your band is on the roster for the dance auditions after school today. Why even bother, McFly? You don't have a chance. You're too much like your old man. No McFly ever amounted to anything in the history of Hill Valley!” In Back to the Future Part II, Marty runs into Strickland in a bleak, alternate 1985, where the teacher has become so unhinged that he engages in shootouts with the town’s “slacker” students.