[[folder:Winslow High Staff]]

!!Steven Harper
-->'''Played by''': Chi [=McBride=]

The principal of Winslow High who has to deal with the wacky antics of his faculty.
* [[BadassTeacher Badass Principal]]: Oh, yes, Steven got his moments. He even ''slammed a bully up against a locker'' in the pilot episode.
* BaldBlackLeaderGuy: He's bald, he's black, and he's the principal of the school.
* BenevolentBoss: Most of the time. [[BewareTheNiceOnes Just don't get on his bad side]].
* BewareTheNiceOnes: Steven is a polite and soft-spoken guy, but you do NOT want to get him angry.
* FormerTeenRebel: In an early episode, he reveals he got drunk and crashed a car. In a Season 2 episode, he admits to having been involved in a robbery.
* LargeAndInCharge: Played by Chi [=McBride=], who is reportedly 6'4".
* OnlySaneMan: Though he does snap once or twice, usually in response to the weird, off-the-wall crap that goes on at Winslow.
%%* ReasonableAuthorityFigure
* TeamDad: To the rest of the faculty.

!!Scott Guber
-->'''Played by''': Anthony Heald

The assistant principal of Winslow High. He's known for being very strict, formal, and authoritarian with both students and teachers.
* TenMinuteRetirement: In the penultimate episode of Season 3, he quits after a student is found dead and he experiences a HeroicBSOD, but come the season finale, he comes back.
* [[BadassTeacher Badass Vice Principal]]: He got his moments.
%%* ButtMonkey
* DontYouDarePityMe: Guber tells his older brother George something along the lines of this when [[spoiler:George explains he hired a call girl for Guber because he felt he was lonely]].
* EtTuBrute: In one episode, Scott is quite furious to find out that his brother George [[spoiler:hired a call girl (who happened to be Scott's girlfriend at the time)]].
%%* HiddenDepths
* InformedJudaism: Occasionally mentions he is Jewish.
* {{Irony}}: Some students call him "The Nazi" not knowing that he's in fact Jewish.
* JerkWithAHeartOfGold: Scott can act like an outright jerk at times, but he does show a soft side from time to time.
* LawfulStupid: A point that Steven calls him on once or twice.
* LookingForLoveInAllTheWrongPlaces: He briefly dates a woman who turns out to be a call girl [[spoiler: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.
* MeanBoss: Contrasting with [[BenevolentBoss Steven]].
%%* OnlySaneMan
* SternTeacher: To the point where students call him "The Nazi."
* ThrowTheDogABone: In the Season 1 finale, he's given a special award, and this is after he was turned down for a Headmaster position at a private school.

!!Lauren Davis
-->'''Played by''': 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.
* DudeWheresMyRespect: She even remarks early on that teachers face disrespect every day from the students because it comes from the parents.
%%* OnlySaneMan
* SternTeacher: This trait is very noticeable toward the end of Season 2. She gets called on this by Marla and ''Guber'' of all people.
* TookALevelInJerkass: In Season 2.

!!Harvey Lipschultz
-->'''Played by''': 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.
%%* BunnyEarsLawyer
%%* HiddenDepths
* InformedJudaism: Mentions he's Jewish on a few occasions.
* LukeYouAreMyFather: Season 2 reveals that [[spoiler:Harvey fathered a son, Lester, with an African-American woman]].
%%* NWordPrivileges
%%* ScrewPolitenessImASenior

!!Harry Senate
-->'''Played by''': 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).
* BadassTeacher: 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.
%%* BunnyEarsLawyer
* DeadpanSnarker:
-->'''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.
%%* {{Flanderization}}
* PutOnABus: In early Season 3.
%%* WellIntentionedExtremist
* WhatTheHellHero: 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
-->'''Played by''': 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.
%%* BadassTeacher
%%* BunnyEarsLawyer
* HotBlooded: Marla was a very passionate and emotional woman. Guber even noted that this is her biggest flaw and the reason why she isn't effective in advocating for herself and others.
* SassyBlackWoman: Yep, she did sass like no one's business.

!!Marilyn Sudor
-->'''Played by''': Sharon Leal

A teacher who also led the student choir.
* HotTeacher: She even topped a student poll about teachers students wanted to sleep with most.
%%* SatelliteCharacter

!!Louisa Fenn
-->'''Played by''': Rashinda Jones

Steven and Scott's secretary. Appears in Seasons 1 and 2. Disappears from the show starting in Season 3.
%%* BrotherChuck
%%* DeadpanSnarker
%%* {{Garfunkel}}
* IJustWantToBeSpecial: [[spoiler:In Season 2, she starts a sex advice column using the alias "Helen." When Steven learns the truth and demands an explanation, Louisa pretty much says she wanted to do something more than file papers and take notes. Steven isn't very sympathetic.]]
* WhatTheHellHero: [[spoiler:Sums up Steven's response to the above trope]].

!!Milton Buttle
-->'''Played by''': 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 ends up fired for it. Appears only in Season 1.
* ButtMonkey: He was often the center of Sheryl Holt's website cartoons.
* PutOnABus: Midway through Season 1.
** TheBusCameBack: For only a few minutes.
* TeacherStudentRomance: With Lisa in Season 1. He gets fired when the relationship is discovered.

!!Kevin Riley
-->'''Played by''': Thomas [=McCarthy=]

A teacher and sports coach. In Season 1, he gets fired for withholding information about Milton's affair with Lisa.
* EtTuBrute: 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 ReasonYouSuckSpeech.
* PutOnABus: Midway through Season 1.
** TheBusCameBack: For one episode. He's never seen again after that.

!!Ronnie Cooke
-->'''Played by''': 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.
* HelloAttorney: Ronnie was a skilled lawyer and very pretty.
* HotTeacher: Ronnie was quite attractive, to say the least. One student even tried asking her out!
%%* PsychologistTeacher

!!Danny Hanson
-->'''Played by''': Creator/MichaelRapaport
%%* BunnyEarsLawyer
%%* CoolTeacher
* DarkAndTroubledPast: He was molested by his priest as a child.
%%* DeadpanSnarker
* FormerTeenRebel: It's stated in one episode that he stole a car when he was a teenager.
%%* HollywoodAtheist
%%* HotBlooded
* JerkWithAHeartOfGold: Danny could act like a jerk at times, but he was a good guy nonetheless.
%%* NayTheist

!!Zach Fischer
-->'''Played by''': Jon Abrahams
%%* BrotherChuck
%%* CoolTeacher
* SuspiciouslySimilarSubstitute: For Harry in Season 3.
%%* WellIntentionedExtremist
%%* WhatTheHellHero

!!Colin Flynn
-->'''Played by''': Joey [=McIntyre=]
%%* BrotherChuck
%%* CoolTeacher
%%* HotTeacher
* LikesOlderWomen: He had an affair with Becky's mom.

!!Kimberly Woods
-->'''Played by''': Michelle Monaghan
* HotTeacher: A male student even ogles [[ShesGotLegs her legs]] and a female student becomes attracted to her.
%%* NaiveNewcomer
%%* PutOnABus
%%* WideEyedIdealist

!!Carmen Torres
-->'''Played by''': Natalia Baron
* TheAlcoholic: She admits she was one.
%%* BrotherChuck
* GratuitousSpanish: Steven calls her on teaching her Physics class in Spanish.
* HotTeacher: She even gets mistaken for a student in her very first episode.
%%* NaiveNewcomer
%%* SpicyLatina

[[folder:Winslow High Students]]

!!Dana Poole
-->'''Played by''': Sarah Thompson
* HotForTeacher: She admitted to having feelings for Harry. They briefly date sometime after she graduated from Winslow and began attending college.

!!Jamal Crenshaw
-->'''Played by''': Edwin Hodge

A student in the "Dungeon" classroom.
%%* BookDumb
* BrotherChuck: The last we see of him, he's serving time in prison.
%%* TheSlacker

!!Brooke Harper
-->'''Played by''': China Jesusita Shavers
%%* PutOnABus
%%* RebelliousSpirit
%%* [[SassyBlackWoman Sassy Black Girl]]
%%* SoapBoxSadie

!!Becky Emerson
-->'''Played by''': 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.
* HotForTeacher: Had a crush on Colin Flynn in Season 3 and was thus devastated to learn that he was having an affair with her mother.

[[folder:Other Characters]]

!!Marsha Shinn
-->'''Played by''': Debbi Morgan

The superintendent of schools in Boston.
* BadBoss: They call her the "Dragon Lady" for a reason.
%%* BrotherChuck
%%* {{Jerkass}}
%%* LawfulStupid
%%* ObstructiveBureaucrat

!!Charlie Bixby
-->'''Played by''': Creator/DennisMiller
%%* BrotherChuck
* DeadpanSnarker: He's played by Creator/DennisMiller, so this is to be expected.
%%* {{Jerkass}}