- Played by: Chi McBride
The principal of Winslow High who regularly has to deal with the wacky antics of his faculty and students.
- Badass Beard: To go hand-in-hand with his Badass Teacher status.
- Badass Teacher: Oh, yes. He even slams Malcolm White up against a locker in the very first episode.
- Bald, Black Leader Guy: He's bald, he's black, and he's the principal of a high school.
- Benevolent Boss: Most of the time. Just don't get on his bad side.
- Beware the Nice Ones: Steven is generally soft-spoken and polite, but you do NOT want to get him angry or annoyed.
- Former Teen Rebel: In an early episode, 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.
- 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.
- Large and in Charge: Played by Chi McBride, who is reportedly 6'4".
- Only Sane Man: 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.
- Scary Black Man: Averted. Chi McBride looks the part (and has played a fair few in his career), but Steven is (usually) benevolent, calm, reasonable, and well-liked.
- Team Dad: To the rest of the faculty.
- Well-Intentioned Extremist: In his appearance in the Boston Legal 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), 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.
- Played by: Anthony Heald
The vice principal of Winslow High, known for being very strict, formal, and authoritarian with both students and teachers.
- 10-Minute Retirement: In the penultimate episode of Season 3, he quits after a student he admired is killed in a shoot-out and he experiences a Heroic BSoD, but come the season finale, thanks to some prodding from Steven, he's back in the game.
- Badass Teacher: He gets his moments to be awesome.
- Don't You Dare Pity Me!: In a Season 1 episode, 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 Season 1 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).
- Heroic BSoD: 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 for her stern behavior, not seeming to acknowledge that 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.
- Informed Judaism: 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.
- Jerk with a Heart of Gold: Scott can act like an outright jerk at times, but he does show a soft side from time to time.
- 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 Blithe Spirit who turns out to be a former porn star.
- Mean Boss: Contrasting with Steven.
- Stern Teacher: To the point where students call him "The Nazi."
- Throw the Dog a Bone: 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.
- 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.
- Chuck Cunningham Syndrome: She disappears from the show after Season 2.
- Dude, Where's My Respect?: She even remarks early on that teachers face disrespect every day from the students because it comes from the parents.
- Stern Teacher: This trait is very noticeable toward the end of Season 2. She gets called on this by Marla and Guber of all people.
- Took a Level in Jerkass: In Season 2.
- Played by: Fyvush Finkel
An 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.
- Informed Judaism: 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.
- Innocent Bigot / Innocently Insensitive: Harvey straddles the line between the two.
- Luke, You Are My Father: Season 2 reveals that Harvey fathered a son, Lester, with an African-American woman.
- N-Word Privileges: 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.
- Your Cheating Heart: Season 2 reveals that he has an affair with an African-American woman, siring a son, Lester, who later comes looking for him.
- 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.
- Badass Teacher: 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.
- Deadpan Snarker: Probably the biggest snarker on the whole show.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?
- Put on a Bus: In early Season 3.
- Well-Intentioned Extremist: He means well, but the way he goes about things tend to be VERY flawed and questionable. Unsurprisingly, he often clashes with his superiors due to this.
- 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.
- Badass Teacher: In Season 4, she slaps a female student who slapped her first after she gives the girl a "Reason You Suck" Speech in response to the girl flippantly saying she can use her sexuality to get ahead in the world.
- Hot-Blooded: Marla is a very passionate and emotional woman. Guber even notes that this is her biggest flaw and the reason she isn't effective in advocating for herself and others.
- Sassy Black Woman: Oh, yes. She isn't afraid to stand up to either one of her bosses, so that qualifies her.
- Played by: Sharon Leal
Another social studies teacher, she also led the student choir.
- Hot Teacher: She even topped a student poll about teachers students wanted to sleep with most!
- Played by: Rashida Jones
Steven and Scott's secretary. She appears in Seasons 1 and 2 before disappearing from the show starting in Season 3.
- Brother Chuck: She isn't seen after Season 2.
- 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 much says she wanted to do something more than file papers and take notes. Steven isn't very sympathetic.
- Mixed Ancestry: She reveals to Harvey in Season 2 that her father is black and her mother is white.
- Servile Snarker: She liked to make witty comments.
- 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.
- Butt-Monkey: He was often the center of Sheryl Holt's website cartoons.
- Put on a Bus: Midway through Season 1.
- The Bus Came Back: For only a few minutes.
- Teacher/Student Romance: With Lisa in Season 1. He gets fired when the relationship is discovered.
- Your Cheating Heart: He started sleeping with Lisa while dating Louisa.
- Played by: 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 replies "Go to Hell, Steven" and proceeds to deliver a "Reason You Suck" Speech.
- Put on a Bus: Midway through Season 1.
- The Bus Came Back: For one episode. He's never seen again after that.
- Played by: Alexondra Lee
A phys ed teacher.
- Fanservice: The very suggestive dance routine she has her cheerleaders do qualifies. So much so that Steven forbids them from participating in a cheer-leading competition.
- Played by: Gina Philips
An attractive English teacher who once had a relationship with Harry Senate.
- Hot for Student: She talks to Tina about how cute a male student in her class and even wonders if he's "hung like an elephant." This almost gets her in trouble when Harvey overhears/mishears the conversation.
- Hot Teacher: Is she ever! Guber himself comments to Steven that she's "a nasty little thing" and is known for flaunting her sexuality. One student ogles her ass and even reaches out to touch it. And Jenna herself doesn't seem bothered by it.
- 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.
- Hello, Attorney!: Ronnie was a skilled lawyer and very pretty.
- Hot Teacher: Ronnie was quite attractive, to say the least. One student even tried asking her out!
- Love Triangle: Becomes involved in one with Dave Fields and Zach in Season 3.
- Played by: Michael Rapaport
A social studies teacher who begins teaching at Winslow High in Season 2.
- Former Teen Rebel: It's stated in one episode that he stole a car when he was a teenager.
- Jerk with a Heart of Gold: Danny could act like a jerk at times, but he was a good guy nonetheless.
- Nay-Theist: He outright states he doesn't believe in God.
- Rape as Backstory: He was molested by his priest as a child.
- 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.
- Abusive Mom: To Jeremy. She even locked him in the basement.
- An Arm and a Leg: 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.
- Manipulative Bitch: In Season 2, she successfully gets Jeremy and Brooke to stop dating.
- Politically Incorrect Villain: 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.
- "The Reason You Suck" Speech: Gives one to Scott after he decides to fire her for hitting Marcie.
- Played by: Jon Abrahams
A science teacher who enters in Season 3. He himself used to be a student at Winslow High years ago.
- Brother Chuck: Disappears after the third season.
- Love Triangle: Becomes involved in one with Dave Fields and Ronnie in Season 3.
- Suspiciously Similar Substitute: For Harry in Season 3.
- Well-Intentioned Extremist: Just like Harry.
- Played by: Joey McIntyre
An English teacher who begins teaching at Winslow High in Season 3.
- Brother Chuck: Disappears after the third season.
- Cool Teacher: He's introduced wearing hip clothes and using a casual vocabulary with students.
- Hot Teacher: Is there any other reason Becky developed a crush on him?
- Teacher/Parent Romance: Engages in one with Patricia Emerson, much to the displeasure of Becky.
- Played by: Michelle Monaghan
A teacher who begins teaching early on in Season 3.
- Hot Teacher: A male student even ogles her legs and a female student becomes attracted to her.
- Naïve Newcomer: Subverted. 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.
- Put on a Bus: For her own safety after she gains a Stalker with a Crush.
- Wide-Eyed Idealist: Played With. While she became a teacher for pretty idealistic and altruistic reasons, it doesn't mean she's out of touch with reality.
- Played by: Natalia Baron
A 21-year-old physics teacher who enters in Season 4.
- The Alcoholic: She admits she was one.
- Brother Chuck: She simply disappeared from the series without a single mention, right after her first and only arc ended.
- Gratuitous Spanish: 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.
- Hot Teacher: She even gets mistaken for a student in her very first episode.
- Played by: Avery Kidd Waddell
A jock whose college prospects are threatened when he purposefully fails two important school tests before a football game with a rival school.
- Brilliant, but Lazy: He has a shiftless nature. Lauren tells him she knows he's smarter than he lets on.
- Brother Chuck: He isn't seen again after "Chapter Five."
- Kick the Son of a Bitch: He assaults Malcolm White and even breaks his arm in defense of Anthony Ward in "Chapter Five." Too bad it gets him suspended.
- Played by: Sarah Thompson
A popular student who kissed Harry Senate and then used the incident to blackmail Harry.
- Blackmail: She gets Harry to change Jason Harrelson's grade so he can play in an important football game and later convince Guber to back down from getting a urine sample from her by threatening to reveal their kiss.
- Hot for Teacher: She admitted to having feelings for Harry.
- Teacher/Student Romance: She and Harry briefly date sometime after she graduated from Winslow and began attending college.
- Played by: John Francis Daley
A nerdy student who was bullied and later started writing stories about killing his tormentors.
- Butt-Monkey: He was often a target for bullies.
- Put on a Bus: 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.
- Played by: Lamya Jezek
The webmistress of Holt 45, a website dedicated to posting mocking cartoons about the various goings-on at Winslow.
- Deadpan Snarker: She certainly didn't have a problem with sassing Steven or Guber.
- Played by: Zachary Ty Bryan
A bully who torments Anthony Ward.
- The Bully: Textbook example.
- Kick the Son of a Bitch: He obviously stuck Anthony in a locker in the pilot. Later on, Steven slams him against a locker while confronting him about putting Anthony in the hospital.
- Too Dumb to Live: Yeah, Malcolm, hover close by the principal while he's talking to the kid you've been terrorizing.
- Played by: Edwin Hodge
A student in the Dungeon classroom.
- Brother Chuck: The last we see of him, he's serving time in prison.
- The Slacker: 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.
- Yank the Dog's Chain: 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.
- Played by: Kaj-Erik Eriksen
An 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.
- Bi the Way: Comes out as this in Season 2. He has relations with a boy, and later flirts with Brooke.
- Brother Chuck: Disappears after Season 2.
- The Dog Bites Back: He snaps and subjects his mother to the same punishment she inflicted upon him—being locked in the basement.
- Played by: Antwon Tanner
A student in Harvey's class whom Scott recruits for his debate team after being impressed with his debating skills.
- Everything Is Racist: When Guber offers for him to join the debate team, Kevin jumps to the conclusion that Guber is only interested in him because he's black. Guber puts him in his place about it.
- Rousing Speech: Gives one in the Season 1 finale during the commencement ceremony.
- Played by: China Jesusita Shavers
Steven and Louanna's rebellious teenage daughter who gets kicked out of her private school, leading to her attending Winslow High.
- MayDecember Romance: She briefly dates a 27-year-old man, much to her father's displeasure.
- Put on a Bus: Leaves for college after Season 3.
- Rebellious Spirit: It's actually what gets her kicked out of private school.
- Sassy Black Woman: She certainly isn't afraid to stand up to her dad.
- Soap Box Sadie: She gets involved in the student protest in the Season 3 premiere.
- 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.
- Attention Deficit... Ooh, Shiny!: 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.
- 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.
- Foil: Her disorganized behavior to Guber's strictness.
- Servile Snarker: To Guber, out of all people. And most importantly, he allows her to do that and even pick-ups some of her Simpleminded Wisdom.
- Played by: Courtney B. Vance
The 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.
- Abusive Parents: His own son mentions to Lauren that Walter calls him "dumb."
- Angry Black Man: The first bit of dialogue we hear in the series is him ranting and raving about Lauren failing his son.
- Jerkass: He has a combative and aggressive demeanor.
- Perpetual Frowner: Pretty much his default expression.
- Played by: Debbi Morgan
The superintendent of schools in Boston.
- Bad Boss: 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.
- Brother Chuck: 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 and cold.
- Obstructive Bureaucrat: Steven even remarks to her that he considers her to be one of many problems he has when it comes to running Winslow.
- Played by: Lynn Whitfield
Steven's ex-wife and Brooke's mother.
- Amicable Exes: She and Steven remain on civil terms for the most part, but they do clash once or twice.
- Hypocrite: She divorced her husband because 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, leaving Brooke to her own devices.
- 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.
- Love Triangle: Becomes involved in one with Ronnie and Zach in Season 3.
- Obstructive Bureaucrat: Steven even notes this in his first appearance.
- Played by: Dennis Miller
- Brother Chuck: 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.
- Deadpan Snarker: He's played by Dennis Miller, 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.
- Jerkass Has a Point: He gives a quasi-Rousing Speech 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 Black Comedy 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?