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1[[foldercontrol]]
2
3[[folder:Winslow High Staff]]
4
5!!Steven Harper
6-->'''Played by''': Creator/ChiMcBride
7
8The principal of Winslow High. He regularly has to deal with the wacky antics of his faculty and students.
9----
10* BadassTeacher: Oh, yes. He even ''slams [[TheBully Malcolm White]] up against a locker'' in the very first episode.
11** In "Chapter Nine", a student takes his class hostage with a gun, and Steven volunteers himself if he lets his classmates go. The student refuses because Steven is way bigger than him and could probably take him out, gun or no.
12* BaldOfAuthority: He's bald, and he's the principal of a high school.
13* BenevolentBoss: Most of the time. [[BewareTheNiceOnes Just don't get on his bad side]].
14* BewareTheNiceOnes: Steven is generally soft-spoken and polite, but you do NOT want to get him angry or annoyed.
15* FormerTeenRebel: In "Chapter Five", he reveals he got drunk and crashed a car when he was young. In a Season 2 episode, he admits to having been involved in a robbery.
16* {{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.
17* LargeAndInCharge: Played by Creator/ChiMcBride, who is reportedly 6'4".
18* OnlySaneMan: Though he does lose his cool a few times, usually in response to any egregious disrespect or the weird and off-the-wall crap that goes on at Winslow High.
19* ReasonableAuthorityFigure: The most level-headed and stable member of the faculty.
20* ScaryBlackMan: {{Averted|Trope}}. Creator/ChiMcBride looks the part (and has played a fair few in his career), but Steven is ([[BewareTheNiceOnes usually]]) benevolent, calm, reasonable, and well-liked.
21* TeamDad: To the rest of the faculty.
22* WellIntentionedExtremist: Anti-heroic example. 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 Fox News). 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.
23
24!!Scott Guber
25-->'''Played by''': Creator/AnthonyHeald
26
27The vice principal of Winslow High. Known for being very strict, formal, and authoritarian with both students and teachers.
28----
29* TenMinuteRetirement: In the penultimate episode of Season 3, he quits after a student he admired is killed in a shoot-out. Come the season finale, thanks to some prodding from Steven, he's back in the game.
30* BadassTeacher: He gets his moments to be awesome.
31%%* ButtMonkey
32* DontYouDarePityMe: In "Chapter Seven", 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]].
33* EtTuBrute: In "Chapter Seven", 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)]].
34* HeroicBSOD: He experiences one in the next-to-last episode of Season 3 after a student he admired is shot and killed.
35* {{Hypocrite}}: In Season 2, he 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.
36* InformedJudaism: He occasionally mentions he is Jewish, and is heard in the Season 2 finale speaking Hebrew to a comatose Harry.
37* {{Irony}}: Some students call him "The Nazi" not knowing that he's in fact Jewish. He even humorlessly comments on it in the penultimate episode of Season 2.
38* JerkWithAHeartOfGold: Scott can act like an outright jerk at times, but he does show a soft side from time to time.
39* LawfulStupid: A point that Steven calls him out on once or twice.
40* 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 Violet Montgomery, a BlitheSpirit who turns out to be a former porn star.
41* MeanBoss: Contrasting with [[BenevolentBoss Steven]].
42* SternTeacher: To the point where students call him "The Nazi."
43* ThrowTheDogABone: In the Season 1 finale, he's given a special award after he was turned down for a headmaster position at a private school in the previous episode.
44
45!!Lauren Davis
46-->'''Played by''': Creator/JessalynGilsig
47
48The head of the Social Studies department. She appears in Seasons 1 and 2 before vanishing from the show at the start of Season 3.
49----
50* ChuckCunninghamSyndrome: She disappears from the show after Season 2.
51* DudeWheresMyRespect: She even remarks early on that teachers face disrespect every day from the students because it comes from the parents.
52* HotTeacher: She was fairly attractive. Plus, footage of her showering ended up on Sheryl Holt's website, leading to her being voted up on the list of sexually desirable teachers.
53* SternTeacher: This trait is very noticeable toward the end of Season 2. She gets called on this by Marla.
54* TookALevelInJerkass: At the start, Lauren was generally a well-intentioned and kind woman. In mid-to-late Season 2, however, Steven and Big Boy express concern that Lauren and Marilyn are pushing their students too hard academically. Lauren doesn't take this very well, outright clashing with Marla when [[WhatTheHellHero she calls her out]] on [[SternTeacher her harsh attitude]]. She does, however, have something of a JerkassRealization after speaking with a student who was hospitalized due to being stressed out by Lauren's demands. A couple of episodes later, she goes on a tear against Scott after he simply questions her about possibly giving students unfair advantages. Scott, for his part, chastises her for her "pissy prima donna attitude." After storming away from Scott, she barks a BigShutUp in response to a visiting Dana Poole's polite greeting. Marla later reiterates to Lauren that she's [[ThePerfectionist perfectionistic]] and [[{{Pride}} acts superior to everyone else]] [[{{Hypocrite}} despite having flaws just like everyone else]].
55
56!!Harvey Lipschultz
57-->'''Played by''': Creator/FyvushFinkel
58
59An elderly history teacher known for his old-fashioned bigotry and obliviousness as to how his thoughtless remarks affect others. He gets partnered with Marla in an attempt by Steven and Scott to balance out their craziness.
60----
61%%* BunnyEarsLawyer
62%%* HiddenDepths
63* InformedJudaism: He mentions he's Jewish on a few occasions, and is heard speaking Hebrew in the Season 2 finale to a comatose Harry, [[ConverseWithTheUnconscious explaining to him]] why he didn't wear scrubs in ICU.
64* InnocentBigot / InnocentlyInsensitive: Harvey straddles the line between the two. Similar to [[Series/AllInTheFamily Archie Bunker]], much humor and drama are derived from his ignorance and bigotry concerning certain matters (especially race), but he's portrayed as well-meaning but ill-informed, and a product of the times he more than likely grew up in.
65* LukeYouAreMyFather: Season 2 reveals that [[spoiler:Harvey fathered a son, Lester, with an African American woman]].
66* NWordPrivileges: In "Chapter Ten", while being confronted about his bigoted views, he uses the term "African American black-colored Negroes." Steven isn't amused.
67* NobleBigot: The "noble" part saves his job in Season 1. In the pilot, he tells Kevin Jackson, a black student, that it's his job to "get your black ass into college." When Harvey is facing termination, Kevin speaks up for him, saying that Harvey will do exactly what he said.
68%%* ScrewPolitenessImASenior
69
70!!Harry Senate
71-->'''Played by''': Creator/NickyKatt
72
73A teacher who's assigned to the Dungeon classroom, which is infamous for its very unruly students. 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.
74----
75* 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 "Chapter Twelve", he was perfectly willing to fight with a bunch of gangbangers in defense of a student.
76%%* BunnyEarsLawyer
77* DeadpanSnarker: Probably the biggest snarker on the whole show.
78-->'''Scott:''' What's going on?
79-->'''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.
80-->'''Scott:''' You think this is funny, Mr. Senate?
81-->'''Harry:''' [[SelfDeprecation I can never do anything right.]]
82* PragmaticHero: He employs ''very'' questionable methods to help his students. Unsurprisingly, he often clashes with Steven and Scott over this.
83* PutOnABus: In early Season 3 due to PTSD.
84
85!!Marla Hendricks
86-->'''Played by''': Creator/LorettaDevine
87
88A 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.
89----
90* 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.
91* BunnyEarsLawyer: Steven even notes that, while Marla can be erratic, she has leadership skills.
92* HotBlooded: Marla is a very passionate and emotional woman.
93* SassyBlackWoman: Oh, yes. She isn't afraid to stand up to either one of her bosses, so that qualifies her.
94
95!!Marilyn Sudor
96-->'''Played by''': Creator/SharonLeal
97
98Another social studies teacher, she also led the student choir.
99----
100* DomesticAbuse: In Season 3, she was revealed to have been abused by her husband. The following season, she confronts her reformed husband.
101* HistoryRepeats: In Season 3, she becomes close to Aisha, a student who's a gifted singer and dating a possessive, abusive boyfriend. It's then revealed Marilyn herself suffered abuse from her husband, and she rightly fears for Aisha.
102* HotTeacher: She even topped a student poll about teachers students wanted to sleep with most!
103%%* SatelliteCharacter
104
105!!Louisa Fenn
106-->'''Played by''': Creator/RashidaJones
107
108Steven and Scott's secretary. She appears in Seasons 1 and 2 before disappearing from the show starting in Season 3.
109----
110* ChuckCunninghamSyndrome: She isn't seen after Season 2.
111%%* {{Garfunkel}}
112* 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.]]
113* ServileSnarker: She liked to make witty comments.
114
115!!Milton Buttle
116-->'''Played by''': Creator/JoeySlotnick
117
118An 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.
119----
120* ButtMonkey: He was often the center of Sheryl Holt's website cartoons.
121* MeaningfulName: Milton ''Buttle'' is often the ''butt'' of people's jokes.
122* PutOnABus: Midway through Season 1.
123** TheBusCameBack: For only a few minutes in "Chapter Fifteen".
124* TeacherStudentRomance: With Lisa in Season 1. He gets fired when the relationship is discovered.
125
126!!Kevin Riley
127-->'''Played by''': Creator/ThomasMcCarthy
128
129A teacher and sports coach. In Season 1, he gets fired for withholding information about Milton's affair with Lisa.
130----
131* 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.
132* ThePiratesWhoDontDoAnything: He's stated to be a teacher, but we don't ever see him teaching anything.
133* PutOnABus: Midway through Season 1.
134** TheBusCameBack: In "Chapter Eighteen". He's never seen again after that.
135
136!!Tina Knowles
137-->'''Played by''': Creator/AlexondraLee
138
139A phys ed teacher.
140----
141* AmbiguouslyGay: Lauren suspects she's a lesbian due to a look she gave her.
142* {{Fanservice}}: The '''very''' suggestive dance routine she has her cheerleaders do qualifies. So much so that Steven forbids them from participating in a cheerleading competition.
143
144!!Jenna Miller
145-->'''Played by''': Creator/GinaPhilips
146
147An attractive English teacher who once had a relationship with Harry Senate.
148----
149* HotTeacher: Is she ever! [[CovertPervert Scott himself]] comments to Steven that she's "a nasty little thing" and is known for flaunting her sexuality. One student [[EatingTheEyeCandy ogles her ass]] and even reaches out to touch it. And Jenna herself doesn't seem bothered by it.
150* TeacherStudentRomance: She talks to Tina about how cute a male student in her class and even wonders if he's "[[BiggerIsBetterInBed hung like an elephant]]." This almost gets her in trouble when Harvey overhears/mishears the conversation.
151
152!!Ronnie Cooke
153-->'''Played by''': Creator/JeriRyan
154
155A 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.
156----
157* HelloAttorney: Ronnie was a skilled lawyer and very pretty.
158* HotTeacher: Ronnie was quite attractive, to say the least. One student even tried asking her out!
159* LoveTriangle: Becomes involved in one with Dave Fields and Zach in Season 3.
160%%* PsychologistTeacher
161
162!!Danny Hanson
163-->'''Played by''': Creator/MichaelRapaport
164
165A social studies teacher who begins teaching at Winslow High in Season 2.
166----
167%%* BunnyEarsLawyer
168* CoolTeacher: He has his students sue Harvey for defamation of character as a class assignment. Plus he regularly holds "Talk Time" for his class, allowing them to discuss certain issues.
169* DeadpanSnarker: He was hardly ever without a wisecrack.
170* FormerTeenRebel: It's stated in one episode that he stole a car when he was a teenager.
171* HotBlooded: A trait he shares with Marla. In fact, they're able to make peace with one another over this in Season 3.
172* JerkWithAHeartOfGold: Danny could act like a jerk at times, but he was a good guy nonetheless.
173* NayTheist: He outright states he doesn't believe in {{God}}.
174* RapeAsBackstory: He was molested by his priest as a child.
175
176!!Meredith Peters
177-->'''Played by''': Creator/KathyBaker
178
179An 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.
180----
181* AbusiveMom: To Jeremy. She even locked him in the basement.
182* AnArmAndALeg: She sliced off her own hand to get free after being tied up in the basement by Jeremy.
183* {{Jerkass}}: She's a nasty piece of work, that's for sure.
184* ManipulativeBitch: In Season 2, she successfully gets Jeremy and Brooke to stop dating.
185* 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.
186* TheReasonYouSuckSpeech: Gives one to Scott after he decides to fire her for hitting Marcie.
187
188!!Zach Fischer
189-->'''Played by''': Creator/JonAbrahams
190
191A science teacher who enters in Season 3. He himself used to be a student at Winslow High years ago.
192----
193* ChuckCunninghamSyndrome: Disappears after the third season.
194* CoolTeacher: He has his students observe a car falling to teach them about physics, and even dissects a corpse in his classroom to teach them biology.
195* LoveTriangle: Becomes involved in one with Dave Fields and Ronnie in Season 3.
196* SuspiciouslySimilarSubstitute: He's basically Harry Senate without any emotional trauma.
197* WellIntentionedExtremist: Just like Harry. He even dissects a corpse in his classroom, which unsurprisingly lands him in hot water with Scott.
198
199!!Colin Flynn
200-->'''Played by''': Creator/JoeyMcIntyre
201
202An English teacher who begins teaching at Winslow High in Season 3.
203----
204* ChuckCunninghamSyndrome: Disappears after the third season.
205* CoolTeacher: He's introduced wearing hip clothes, using a casual vocabulary with students, and letting students address him by his first name.
206* HotTeacher: Is there any other reason Becky developed a crush on him?
207* TeacherParentRomance: Engages in one with Patricia Emerson, much to the displeasure of Becky.
208
209!!Kimberly Woods
210-->'''Played by''': Creator/MichelleMonaghan
211
212A teacher who begins teaching early on in Season 3.
213----
214* HotTeacher: A male student even ogles [[LegFocus her legs]] and a female student becomes attracted to her.
215* 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 all end up admitting they've cheated...only to learn the whole thing was a ruse to get their confessions.
216* PutOnABus: For her own safety after she gains a StalkerWithACrush.
217* WideEyedIdealist: PlayedWith. While she became a teacher for pretty idealistic and altruistic reasons, it doesn't mean she's out of touch with reality.
218
219!!Carmen Torres
220-->'''Played by''': Creator/NataliaBaron
221
222A 21-year-old physics teacher who enters in Season 4.
223----
224* TheAlcoholic: She admits she was one.
225* ChuckCunninghamSyndrome: She simply disappeared from the series without a single mention, right after her first and only arc ended.
226* GratuitousSpanish: Steven calls her on teaching her class in Spanish. (Ironically, the show never addressed the fact that some schools in Massachusetts have an English-only mandate.)
227* HotTeacher: She even gets mistaken for a student in her very first episode and Harvey even comes onto her in his QuestForSex to stave off Alzheimer's.
228%%* NaiveNewcomer
229%%* SpicyLatina
230[[/folder]]
231
232[[folder:Winslow High Students]]
233
234!!Jason Harrelson
235-->'''Played by:''' Creator/AveryKiddWaddell
236
237A jock whose college prospects are threatened when he purposefully fails two important school tests before a football game with a rival school.
238----
239* BrilliantButLazy: He has a shiftless nature. Lauren tells him he's smarter than he lets on.
240* ChuckCunninghamSyndrome: He isn't seen again after "Chapter Five."
241
242!!Dana Poole
243-->'''Played by''': Creator/SarahThompson
244
245A popular student who kissed Harry Senate and then used the incident to blackmail Harry.
246----
247* {{Blackmail}}: She gets Harry to change Jason Harrelson's grade so he can play in an important football game and later convince Scott to back down from getting a urine sample from her by threatening to reveal their kiss.
248* TeacherStudentRomance: She and Harry briefly date sometime after she graduated from Winslow and began attending college.
249
250!!Anthony Ward
251-->'''Played by''': Creator/JohnFrancisDaley
252
253A nerdy student who was bullied. He later started writing about killing his tormentors in his journal, which was discovered.
254----
255* ButtMonkey: He was often a target for bullies.
256* IdiotBall: If Anthony had kept his journal at home in the first place, he ultimately wouldn't have been transferred to another school.
257* NightmareFetishist: He thinks it's fun to imagine his bullies dead and wrote his fantasies in his journal.
258* PutOnABus: Late in Season 1, Superintendent Shinn has him transferred to another school to give him a fresh start after she learns about his hit list.
259
260!!Sheryl Holt
261-->'''Played by''': Creator/LamyaJezek
262
263The webmistress of Holt 45, a website dedicated to posting mocking cartoons about the various goings-on at Winslow.
264----
265* DeadpanSnarker: She certainly didn't have a problem with sassing Steven or Scott.
266* KnowledgeBroker: She had a close eye on current events taking place in the school. Steven and Lauren even approached her for info at separate points.
267%%* LoopholeAbuse
268
269!!Malcolm White
270-->'''Played by''': Creator/ZacheryTyBryan
271
272A bully who torments Anthony Ward.
273----
274* TheBully: Textbook example.
275* TooDumbToLive: Yeah, Malcolm, hover close by the principal while he's talking to the kid you've been terrorizing.
276
277!!Jamal Crenshaw
278-->'''Played by''': Creator/EdwinHodge
279
280A student in the Dungeon classroom.
281----
282* ApatheticStudent: 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.
283* ChuckCunninghamSyndrome: The last we see of him, he's serving time in prison.
284* 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.
285
286!!Lisa Greer
287-->'''Played by''': Creator/BiancaKaijich
288
289A student who begins a relationship with Milton Buttle that results in him being fired.
290----
291* KarmaHoudini: Despite deceiving Milton into starting a relationship with her, she receives no punishment for this. She even avoids being transferred and is allowed to remain at Winslow as a teacher.
292
293!!Jeremy Peters
294-->'''Played by''': Creator/KajErikEriksen
295
296An 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.
297----
298* ChuckCunninghamSyndrome: Disappears after Season 2.
299* TheDogBitesBack: He snaps and subjects his mother to the same punishment she inflicted upon him--being locked in the basement.
300* MaddenIntoMisanthropy: Textbook example. His mother's abuse ultimately results in him snapping, locking her in their basement, and becoming more confident, a far cry from his original depiction as a straitlaced overachiever.
301* StraightGay: Doesn't show any CampGay behavior despite being bisexual.
302
303!!Kevin Jackson
304-->'''Played by''': Creator/AntwonTanner
305
306A student in Harvey's class whom Scott recruits for his debate team after being impressed with his debating skills.
307----
308* EverythingIsRacist: When Scott offers for him to join the debate team, Kevin jumps to the conclusion that he's only interested in him because he's black. Scott puts him in his place about it.
309* RousingSpeech: Gives one in the Season 1 finale during the graduation ceremony.
310
311!!Brooke Harper
312-->'''Played by''': Creator/ChinaJesusitaShavers
313
314Steven and Louanna's rebellious teenage daughter who gets kicked out of her private school, leading to her attending Winslow High.
315----
316* AgeGapRomance: She's a teen who briefly dates a 27-year-old insurance adjuster, much to her father's displeasure.
317* PutOnABus: Leaves for college after Season 3.
318* RebelliousSpirit: It's actually what gets her kicked out of private school.
319* SassyBlackWoman: She certainly isn't afraid to stand up to her dad.
320* SoapBoxSadie: She gets involved in the student protest in the Season 3 premiere.
321
322!!Marcie Kendall
323-->'''Played By:''' Creator/CaraDeLizia
324----
325* ServileSnarker: Much like Louisa.
326* TeenPregnancy: Midway through Season 3, she becomes pregnant by her boyfriend.
327
328!!Becky Emerson
329-->'''Played by''': Creator/CourtneyPeldon
330
331A student who appears in Season 3 as a student in Colin Flynn's class. In Season 4, she becomes Scott's assistant.
332----
333* 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.
334* HotScoop: She also worked as a reporter for the school's TV station, and is played by the attractive Courtney Peldon.
335* {{Foil}}: Her disorganized behavior to Scott's strictness.
336* ServileSnarker: To Scott, out of all people. And most importantly, he allows her to do that and even picks up some of her SimplemindedWisdom.
337* TeacherStudentRomance: Had a crush on Colin Flynn in Season 3 and was thus devastated to learn that he was having an affair with her mother.
338[[/folder]]
339
340[[folder:Other Characters]]
341!!Walter Harrellson
342-->'''Played by''': Creator/CourtneyBVance
343
344The father of Jason Harrellson, a football jock whose failing grades prevented him from playing in an important game until Harry Senate changed his grade at the behest of Dana Poole.
345----
346* AbusiveParents: He's implied to be emotionally abusive to Jason who mentions to Lauren that Walter calls him "dumb."
347* AdultsAreUseless: One of the more egregious examples in the show. Most tellingly, he expects the teachers to give his son the lessons he himself could have easily given to Jason, yet insists upon [[NeverMyFault blaming the teachers for Jason's failures]].
348* AngryBlackManStereotype: The first bit of dialogue we hear in the series is him ranting and raving about Lauren failing his son. He later accuses Steven of selling out when the principal suspends Jason for breaking Malcolm White's arm.
349* {{Jerkass}}: He has a combative and aggressive demeanor.
350* NeverMyFault: Blames the faculty for his son's academic failures rather than completely accept his own role in Jason's apathy towards his studies.
351* PerpetualFrowner: Pretty much his default expression.
352
353!!Marsha Shinn
354-->'''Played by''': Creator/DebbiMorgan
355
356The superintendent of schools in Boston.
357----
358* 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.
359* ChuckCunninghamSyndrome: 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.
360* {{Jerkass}}: She's very unpleasant and cold.
361* ObstructiveBureaucrat: Steven even remarks right to her face that he considers her to be one of many problems he has when it comes to running Winslow.
362
363!!Louanna Harper
364-->'''Played by''': Creator/LynnWhitfield
365
366Steven's ex-wife and Brooke's mother.
367----
368* AmicableExes: She and Steven remain on civil terms for the most part, but they do clash once or twice.
369* {{Hypocrite}}: She divorced her husband because [[WhenYouComingHomeDad he was hardly ever home]] and continues to give him crap about always being at school, yet she herself is often out of town on business.
370
371!!Dave Fields
372-->'''Played by''': Creator/DavidConrad
373
374An official from the Mayor's office who comes to Winslow High to supposedly help the school meet district requirements and get more funding.
375----
376* LoveTriangle: Becomes involved in one with Ronnie and Zach in Season 3.
377* ObstructiveBureaucrat: Steven even notes this in his first appearance.
378-->'''Steven:''' Mr. Fields, you are not here to help us; you are here to help the Mayor get re-elected.
379
380!!Charlie Bixby
381-->'''Played by''': Creator/DennisMiller
382
383An investment banker convicted of securities fraud who is forced to teach math at Winslow High as community work to lessen his sentence in Season 4.
384----
385* ChuckCunninghamSyndrome: He disappears 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.
386* DeadpanSnarker: He's played by Creator/DennisMiller, so this is to be expected.
387* {{Jerkass}}: He's an investment banker doing community work to lessen his sentence, so it's a given. Then comes [[ApatheticTeacher his utter disrespect towards being a teacher]] and absolute LackOfEmpathy toward students, as he considers the whole thing just a temporary stop and minor setback in his banking career.
388* 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 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.
389-->'''Charlie:''' ''[to Guber]'' Do you think your cookie-cutter, bureaucratic approach to all of this just might be the reason that public schools suck so much?
390* ThirdPersonPerson: He had a habit of repeating his own name.
391[[/folder]]

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