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Winslow High Staff
Steven Harper (Chi McBride)
The principal of Winslow High who has to deal with the wacky antics of his faculty.
Scott Guber (Anthony Heald)
The assistant principal of Winslow High. Known for being very strict, formal, and authoritarian with both students and teachers.
- Don't You Dare Pity Me!: Guber tells his older brother George something along the lines of this when George explains he hired a call girl for Guber because he felt he was lonely.
- Et Tu, Brute?: In one episode, Scott is quite furious to find out that his brother George hired a call girl (who happened to be Scott's girlfriend at the time).
- Informed Judaism: Occasionally mentions he is Jewish.
- Irony: Some students nickname him "the Nazi" not knowing that he's in fact Jewish.
- Jerk with a Heart of Gold: Scott can act like an outright jerk at times, but he does have a soft side to him and can be rather nice and kindhearted when he needs to be.
- Lawful Stupid: A point that Steven calls him on once or twice.
- Looking for Love in All the Wrong Places: He briefly dates a woman who turns out to be a call girl hired by his brother, hopelessly pursues Lauren and later Marilyn, and dates Meredith "Hook Lady" Peters until he finally finds love in a woman who turns out to be a former porn star.
- Mean Boss: Contrasting with Steven.
Lauren Davis (Jessalyn Gilsig)
The head of the Social Studies department. Appears in Seasons 1 and 2 before vanishing from the show at the start of Season 3.
Harvey Lipschultz (Fyvush Finkel)
An elderly History teacher, known for being a bigot and completely unaware of how his racist remarks make people feel. He gets partnered with Marla in an attempt by Steven and Scott to balance out their craziness.
Harry Senate (Nicky Katt)
A teacher known for employing highly questionable tactics to try and help his students. Appearing in Seasons 1 and 2, he leaves during Season 3 after a serious case of post-traumatic stress disorder (resulting from being attacked by a former student at the end of the second season).
- Badass Teacher: Come on, he's the one who set the very unruly students in the Dungeon in line (by firing off a gun in the class), plus in one episode, he seemed perfectly willing to fight with a bunch of gang-bangers in defense of a student.
- Deadpan Snarker:
Guber: What's going on?
Harry: Lipschultz told all the girls in his glass to wear a bra for the good of the country. Turns out they're all a bunch of Communist sluts.
Guber: You think this is funny, Mr. Senate?
Harry: I can never do anything right.
- What the Hell, Hero?: A prominent example is the whole situation with a student who was trying to leave a street gang after killing a rival gang member in self-defense. Harry receives an especially harsh dressing-down from Steven for keeping quiet about the whole thing.
Marla Hendricks (Loretta Devine)
A teacher who has to take medication to manage her mental illness. Used to teach in the Dungeon until the students there drove her...well, crazy, only to later be paired up with Harvey for a brief time.
Marilyn Sudor (Sharon Leal)
A teacher who also led the student choir.
- Hot Teacher: She even topped a student poll about teachers students wanted to sleep with most.
Louisa Fenn (Rashinda Jones)
Steven and Scott's secretary. Appears in Seasons 1 and 2. Disappears from the show starting in Season 3.
- I Just Want to Be Special: In Season 2, she starts a sex advice column using the alias "Helen." When Steven learns the truth and demands an explanation, Louisa pretty says she wanted to do something more than file papers and take notes. Steven isn't very sympathetic.
- What the Hell, Hero?: Sums up Steven's response to the above trope.
Milton Buttle (Joey Slotnick)
An English teacher who was often the subject of ridicule on Sheryl Holt's website cartoons. He later began a relationship with Lisa Greer, only to find out she was a student at Winslow High and later end up fired. Appears only in Season 1.
Kevin Riley (Thomas McCarthy)
A teacher and sports coach. In Season 1, he gets fired for withholding information about Milton's affair with Lisa.
- Et Tu, Brute?: Kevin was quite angry when Steven spoke against his keeping Milton's relationship with Lisa secret. When Steven tries to clear the air between them, he just replies "Go to Hell, Steven" and proceeds to deliver a "Reason You Suck" Speech.
- Put on a Bus: Midway through Season 1.
Ronnie Cooke (Jeri Ryan)
A wealthy and successful lawyer who decides to give up law in favor of teaching after being impressed by how Harry, a college friend of hers, handled the students in the Dungeon.
- Hot Teacher: Ronnie was quite attractive, to say the least. One student even tried asking her out!
- Former Teen Rebel: It's stated in one episode that he stole a car when he was a teenager.
Zach Fischer (Jon Abrahams)
Colin Flynn (Joey McIntyre)
Kimberly Woods (Michelle Monaghan)
- Hot Teacher: A male student even oogles her legs and a female student becomes attracted to her.
Carmen Torres (Natalia Baron)
- Gratuitous Spanish: Steven calls her on teaching her Physics class in Spanish.
- Hot Teacher: She even gets mistaken for a student in her very first episode.
Winslow High Students
Dana Poole (Sarah Thompson)
- Hot for Teacher: She admitted to having feelings for Harry. They briefly date sometime after she graduated from Winslow and began attending college.
Jamal Crenshaw (Edwin Hodge)
A student in the "Dungeon" classroom.
- Brother Chuck: The last we see of him, he's serving time in prison.
Brooke Harper (China Jesusita Shavers)
Becky Emerson (Courtney Peldon)
A student who appears in Season 3 as a student in Colin Flynn's class. In Season 4, she becomes Scott's assistant.
- Hot for Teacher: Had a crush on Colin Flynn in Season 3 and was thus devastated to learn that he was having an affair with her mother.
Marsha Shinn (Debbi Morgan)
The superintendent of schools in Boston.
- Bad Boss: They call her the "Dragon Lady" for a reason.