[[folder:Winslow High Staff]]

!!Steven Harper (Chi [=McBride=])

The principal of Winslow High.

* BaldBlackLeaderGuy: He's bald, he's black, and he's the principal of the school.
* BenevolentBoss: Most of the time.
* 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 being involved in a robbery.
* LargeAndInCharge: Played by Chi [=McBride=], who is reportedly 6'4".
* OnlySaneMan: Though he does snap once or twice.
%%* ReasonableAuthorityFigure
* TeamDad: To the rest of the faculty.

!!Scott Guber (Anthony Heald)

The assistant principal of Winslow High.

%%* BadassTeacher
%%* ButtMonkey
* 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 nickname him "the Nazi" not knowing that he's in fact Jewish.
* JerkWithAHeartOfGold: Scott can act like an outright jerk at times, but he does have a soft side to him and can be rather nice and more kindhearted when he needs to be.
* LawfulStupid: A point that Steven calls him on at one point.
* 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."

!!Lauren Davis (Jessalyn Gilsig)

The head of the Social Studies department.

%%* OnlySaneMan
* SternTeacher: 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 (Fyvush Finkel)

%%* 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]].
%%* ScrewPolitenessImASenior

!!Harry Senate (Nicky Katt)

* 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 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''': 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 (Loretta Devine)

%%* BadassTeacher
%%* BunnyEarsLawyer
* HotBlooded: Marla was a very passionate and emotional woman.
* SassyBlackWoman: Yep, she did sass like no one's business.

!!Marilyn Sudor (Sharon Leal)

* HotTeacher: She even topped a student poll about teachers students wanted to sleep with most.
%%* SatelliteCharacter

!!Louisa Fenn (Rashinda Jones)

Steven and Scott's secretary.

%%* 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 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 (Joey Slotnick)

* ButtMonkey: He was often the center of Sheryl Holt's website cartoons.
* PutOnABus
** TheBusCameBack: For only a few minutes.
* TeacherStudentRomance: With Lisa in Season 1. He gets fired when the relationship is discovered.

!!Kevin Riley (Thomas [=McCarthy=])

* [[EtTuBrute Et Tu, Steven?]]: 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."
* PutOnABus
** TheBusCameBack: For one episode. He's never seen again after that.

!!Ronnie Cooke (Jeri Ryan)

* HotTeacher: Ronnie was quite attractive, to say the least. One student even tried asking her out!
%%* PsychologistTeacher

!!Danny Hanson (Michael Rapaport)

%%* BunnyEarsLawyer
%%* CoolTeacher
* DarkAndTroubledPast: He was molested by his priest.
%%* 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 (Jon Abrahams)

%%* BrotherChuck
%%* CoolTeacher
* SuspiciouslySimilarSubstitute: For Harry in Season 3.
%%* WellIntentionedExtremist
%%* WhatTheHellHero

!!Colin Flynn (Joey [=McIntyre=])

%%* BrotherChuck
%%* CoolTeacher
%%* HotTeacher
* LikesOlderWomen: He had an affair with Becky's mom.

!!Kimberly Woods (Michelle Monaghan)

* HotTeacher: A male student even oogles [[ShesGotLegs her legs]] and a female student becomes attracted to her.
%%* NaiveNewcomer
%%* PutOnABus
%%* WideEyedIdealist

!!Carmen Torres (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 (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 (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 (China Jesusita Shavers)

%%* PutOnABus
%%* RebelliousSpirit
%%* [[SassyBlackWoman Sassy Black Girl]]
%%* SoapBoxSadie

!!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.

* HotForTeacher: Had a crush on Colin in Season 3 and was thus devastated to learn that he was having an affair with her mother.


[[folder:Other Characters]]

!!Marsha Shinn (Debbi Morgan)

The superintendent of schools in Boston.

* BadBoss: They call her the "Dragon Lady" for a reason.
%%* BrotherChuck
%%* {{Jerkass}}
%%* LawfulStupid
%%* ObstructiveBureaucrat

!!Charlie Bixby (Creator/DennisMiller)

%%* BrotherChuck
* DeadpanSnarker: He's played by Creator/DennisMiller.
%%* {{Jerkass}}