[[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: Oh, yes, he gets plenty of moments to be badass. He even ''slams a bully up against a locker'' in the very first episode.
* BaldBlackLeaderGuy: He's bald, he's black, and he's the principal of a high school.
* BenevolentBoss: Most of the time. [[BewareTheNiceOnes Just don't get on his bad side]].
* BewareTheNiceOnes: Steven is a generally soft-spoken and polite guy, but you do NOT want to get him angry or annoyed.
* 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.
* {{Hypocrite}}: In the Season 4 episode where Marla slaps a student who slapped her, Steven chastises Marla for her actions and refuses to give her his support against any criticism or punitive action. This, coming from the guy who slammed a student against a locker in the show's very first episode.
* LargeAndInCharge: Played by Chi [=McBride=], who is reportedly 6'4".
* OnlySaneMan: Though he does lose his cool once or twice, usually in response to the weird and off-the-wall crap that goes on at Winslow High.
%%* ReasonableAuthorityFigure
* ScaryBlackMan: {{Averted|Trope}}. Chi [=McBride=] looks the part (and has played a fair few in his career), but Steven is ([[BewareTheNiceOnes usually]]) benevolent, calm, reasonable, and well-liked.
* TeamDad: To the rest of the faculty.
* WellIntentionedExtremist: In his appearance in the ''Series/BostonLegal'' {{crossover}} episode "Let Sales Ring," Steven is involved in a court case which involves him installing filtering devices that blocks a television news channel (implied to be Creator/FoxNews), and his explanation for doing so is basically that he was trying to protect the students against fights that break out over the issue of politics. The judge presiding over the case, however, rules in favor of a student who opposes Steven's actions and even notes to Steven that, while his intentions are good, what he's doing is still censorship.

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

The assistant principal of Winslow High, 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 he admired is killed in a shoot-out and he experiences a HeroicBSOD, but come the season finale, thanks to some prodding from Steven, he's back in the game.
* BadassTeacher: He gets his moments to be awesome.
%%* ButtMonkey
* DontYouDarePityMe: In a Season 1 episode, 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 Season 1 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)]].
* HeroicBSOD: He experiences one in the next-to-last episode of Season 3 after a student he admired is shot and killed.
* {{Hypocrite}}: In Season 2, he chastises Lauren to her stern behavior, not acknowledging he himself is the same way with both students and staff. That same season, he also chastises Ronnie for acting out on her grief in relation to a beloved student, but when it happens to him near the end of Season 3, he goes so far as to hand in his resignation.
* InformedJudaism: Guber occasionally mentions he is Jewish, and is heard in the Season 2 finale speaking Hebrew to a comatose Harry.
* {{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 [[spoiler: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.
* 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. She appears in Seasons 1 and 2 before vanishing from the show at the start of Season 3.
* ChuckCunninghamSyndrome: She disappears from the show after Season 2.
* 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 his bigotry and obliviousness as to how his thoughtlessly-racist remarks affect others. He gets partnered with Marla in an attempt by Steven and Scott to balance out their craziness.
%%* BunnyEarsLawyer
%%* HiddenDepths
* InformedJudaism: He mentions he's Jewish on a few occasions, and is heard speaking Hebrew in a Season 2 episode to a comatose Harry explaining why he didn't wear scrubs in ICU.
* LukeYouAreMyFather: Season 2 reveals that [[spoiler:Harvey fathered a son, Lester, with an African-American woman]].
* NWordPrivileges: In one Season 1 episode, while being confronted about his old-fashioned views, he uses the term "African-American black-colored Negroes." Steven isn't amused.
%%* ScrewPolitenessImASenior
* YourCheatingHeart: [[spoiler:Season 2 reveals that he has an affair with an African-American woman, siring a son, Lester, who later comes looking for him.]]

!!Harry Senate
-->'''Played by''': Nicky Katt

A teacher who's assigned to the Dungeon classroom, which is infamous for its very unruly students, and he quickly becomes 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 students in the Dungeon in line (by ''firing off a gun in the class''), plus in one episode, he was perfectly willing to fight with a bunch of gangbangers 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''': [[SelfDeprecation I can never do anything right.]]
%%* {{Flanderization}}
* PutOnABus: In early Season 3.
* WellIntentionedExtremist: He means well, but the way he goes about things tend to be VERY flawed and questionable.
* 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 social studies teacher who has to take medication to manage her mental illness. She 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: In Season 4, she slaps a female student who slapped her first after she gives the girl a ReasonYouSuckSpeech in response to the girl flippantly saying she can use her sexuality to get ahead in the world.
%%* BunnyEarsLawyer
* HotBlooded: Marla is a very passionate and emotional woman. Guber even notes that this is [[FatalFlaw her biggest flaw]] and the reason she isn't effective in advocating for herself and others.
* SassyBlackWoman: Oh, yes. She isn't afraid to stand up to either one of her bosses, so that qualifies her.

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

Another social studies teacher, she 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''': Creator/RashidaJones

Steven and Scott's secretary. She appears in Seasons 1 and 2 before disappearing from the show starting in Season 3.
* BrotherChuck: She isn't seen after Season 2.
%%* {{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.]]
* MixedAncestry: She reveals to Harvey in Season 2 that her father is black and her mother is white.
* ServileSnarker: She liked to make witty comments.
* 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 ended 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.
* YourCheatingHeart: He started sleeping with Lisa while dating Louisa.

!!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 replies "Go to Hell, Steven" and proceeds to deliver a ReasonYouSuckSpeech.
%%* JerkassHasAPoint
* 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 practicing 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!
* LoveTriangle: Becomes involved in one with Dave Fields and Zach in Season 3.
%%* PsychologistTeacher

!!Danny Hanson
-->'''Played by''': Creator/MichaelRapaport

A social studies teacher who begins teaching at Winslow High in Season 2.
%%* BunnyEarsLawyer
%%* CoolTeacher
%%* DeadpanSnarker
* FormerTeenRebel: It's stated in one episode that he stole a car when he was a teenager.
%%* HotBlooded
* JerkWithAHeartOfGold: Danny could act like a jerk at times, but he was a good guy nonetheless.
* NayTheist: He outright states he doesn't believe in {{God}}.
* RapeAsBackstory: He was molested by his priest as a child.

!!Meredith Peters
-->'''Played by''': Kathy Baker

An abusive mother who joins the staff as a teaching assistant and later a teacher. She and Scott briefly date until they break up after she hits a student with her hook hand.
* AbusiveMom: To Jeremy. She even locked him in the basement.
* AnArmAndALeg: She sliced off her own hand to get free after being tied up in the basement by Jeremy.
* {{Jerkass}}: She's a nasty piece of work, that's for sure.
* ManipulativeBitch: In Season 2, she successfully gets Jeremy and Brooke to stop dating.
* PoliticallyIncorrectVillain: She's homophobic (she's appalled to find out that her son had sex with another boy) and racist (she successfully gets Jeremy to stop dating Brooke, a black girl). Scott even calls her on it at one point.
* TheReasonYouSuckSpeech: Gives one to Scott after he decides to fire her for hitting Marcie.

!!Zach Fischer
-->'''Played by''': Jon Abrahams

A science teacher who enters in Season 3. He himself used to be a student at Winslow High years ago.
* BrotherChuck: Disappears after the third season.
%%* CoolTeacher
* LoveTriangle: Becomes involved in one with Dave Fields and Ronnie in Season 3.
* SuspiciouslySimilarSubstitute: For Harry in Season 3.
* WellIntentionedExtremist: Just like Harry.
%%* WhatTheHellHero

!!Colin Flynn
-->'''Played by''': Joey [=McIntyre=]

An English teacher who begins teaching at Winslow High in Season 3.
%%* BrotherChuck
%%* CoolTeacher
%%* HotTeacher

!!Kimberly Woods
-->'''Played by''': Michelle Monaghan

A teacher who begins teaching early on in Season 3.
* HotTeacher: A male student even ogles [[ShesGotLegs her legs]] and a female student becomes attracted to her.
* NaiveNewcomer: {{Subverted|Trope}}. After apparently her entire class easily tricked her into letting them all go, she creates an elaborate scheme to set them up. To avoid painful medical examination, they've all end up admitting they've cheated...only to learn the whole thing was a ruse to get their confessions.
* PutOnABus: For her own safety after she gains a StalkerWithACrush.
* WideEyedIdealist: PlayedWith. While she became a teacher for pretty idealistic and altruistic reasons, it doesn't mean she's out of touch with reality.

!!Carmen Torres
-->'''Played by''': Natalia Baron

A physics teacher who enters in Season 4.
* TheAlcoholic: She admits she was one.
* BrotherChuck: She simply disappeared from the series without a single mention, right after her first and only arc ended.
* GratuitousSpanish: Steven calls her on teaching her 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.

!!Anthony Ward
-->Played by: John Francis Daley
* ButtMonkey: He was often a target for bullies.

!!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: He's shown to be quite lazy, but Harry helps motivate him to do better and get into college. That is, until he ends up doing time in prison for his brother's crimes.
* WhatTheHellHero: He gets chewed out by Harry in Season 2 for plagiarizing his college application essay (he bought it off the Internet).
* YankTheDogsChain: He gets into college on his own merits, but then he gets arrested for his brother's murder of a convenience store clerk. The last time he's seen, he's still in prison and is no longer interested in attending college.

!!Jeremy Peters
-->'''Played by''': Kaj-Erik Eriksen

A honors student who was abused by his mother, Meredith. He finally snaps, locks his mother in the basement, and starts exhibiting a more rebellious personality.
* BiTheWay: Comes out as this in Season 2. He has relations with a boy, and later flirts with Brooke.
* BrotherChuck: Disappears after Season 2.
* TheDogBitesBack: He snaps and subjects his mother to the same punishment she inflicted upon him--being locked in the basement.
* StraightGay: Doesn't show any CampGay behavior despite being bisexual.

!!Kevin Jackson
-->'''Played by''': Antwon Tanner

A student in Harvey's class whom Scott recruits for his debate team after being impressed with his debating skills.
%%* EverythingIsRacist

!!Brooke Harper
-->'''Played by''': China Jesusita Shavers

Steven's rebellious teenage daughter who gets kicked out of her private school, leading to her attending Winslow High.
* PutOnABus: Leaves for college after Season 3.
* RebelliousSpirit: It's actually what gets her kicked out of private school.
* SassyBlackWoman: She isn't afraid to stand up to her dad.
* SoapBoxSadie: She gets involved in the student protest in the Season 3 premiere.

!!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.
* AttentionDeficitOohShiny: She's so easily distracted by things around her, it's amazing she didn't cause any serious accidents. To fight that at least a bit, Ronnie bought her a notebook to arrange the counseling appointments, only for Becky to forget about the notebook itself.
* 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.
* {{Foil}}: Her disorganized behaviour to Guber's strictness.
* ServileSnarker: To Guber, out of all people. And most importantly, he allows her to do that and even pick-ups some of her SimplemindedWisdom.

[[folder:Other Characters]]

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

The superintendent of schools in Boston.
* BadBoss: She seemed more interested in trying to get Steven fired for both his actions and the antics of his faculty than actually trying to support him and help defend his actions to the school board. She's called the "Dragon Lady" for a reason.
* BrotherChuck: She appears only in Season 1 and is mentioned a couple of times in Season 2 before finally being replaced with Elizabeth Vasquez in Season 3.
* {{Jerkass}}: She's very unpleasant. Steven even remarks to her that he considers her to be one of many problems he has when it comes to running Winslow.
%%* LawfulStupid
%%* ObstructiveBureaucrat

!!Dave Fields
-->'''Played by''': David Conrad

An official from the Mayor's office who comes to Winslow High to supposedly help the school meet district requirements and get more funding.
* LoveTriangle: Becomes involved in one with Ronnie and Zach in Season 3.
* ObstructiveBureaucrat: Steven even notes this.

!!Charlie Bixby
-->'''Played by''': Creator/DennisMiller
* BrotherChuck: He disappeared without a single mention, but unlike most of characters sharing this fate, at least he's semi-justified; he was a temp teacher with a specific amount of community work to do.
* DeadpanSnarker: He's played by Creator/DennisMiller, so this is to be expected.
* {{Jerkass}}: He's an investment banker doing community work to lessen his sentence, so it's a given. Then comes his utter disrespect towards being a teacher and absolute {{lack of empathy}} toward students, as he considers the whole thing just a temporary stop and minor setback in his banking career.
* JerkassHasAPoint: He gives a quasi-RousingSpeech to his students how math is one of the few ways to avoid ending up in [=McDonald=]'s. But most importantly, the confrontation with Guber about the way he handles his math classes: Pretending his students don't come from bad neighborhoods won't suddenly rewrite the reality, while basing all the math exercises on BlackComedy and "pimp accounting" at least keeps them really interested and focused on the class.
-->'''Charlie''': Do you think your cookie-cutter, bureaucratic approach to all of this just might be the reason that public schools suck so much?