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Winslow High Staff
Steven Harper
- Played by: Chi McBride
The principal of Winslow High. He regularly has to deal with the wacky antics of his faculty and students.
- Badass Teacher: Oh, yes. He even slams Malcolm White up against a locker in the very first episode.
- 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.
- Bald of Authority: He's bald, 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 "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.
- 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.
- Reasonable Authority Figure: The most level-headed and stable member of the faculty.
- 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: Anti-heroic example. 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). 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 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. 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 "Chapter Seven", 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 "Chapter Seven", 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 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: He 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. He even humorlessly comments on it in the penultimate episode of Season 2.
- 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 out 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 Violet Montgomery, 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.
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.
- 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.
- Hot Teacher: 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.
- Stern Teacher: This trait is very noticeable toward the end of Season 2. She gets called on this by Marla.
- Took a Level in Jerkass: 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 she calls her out on her harsh attitude. She does, however, have something of a Jerkass Realization 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 Big "SHUT UP!" in response to a visiting Dana Poole's polite greeting. Marla later reiterates to Lauren that she's perfectionistic and acts superior to everyone else despite having flaws just like everyone else.
Harvey Lipschultz
- 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 the Season 2 finale to a comatose Harry, explaining to him why he didn't wear scrubs in ICU.
- Innocent Bigot / Innocently Insensitive: Harvey straddles the line between the two. Similar to 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.
- Luke, You Are My Father: Season 2 reveals that Harvey fathered a son, Lester, with an African American woman.
- N-Word Privileges: In "Chapter Ten", while being confronted about his bigoted views, he uses the term "African American black-colored Negroes." Steven isn't amused.
- Noble Bigot: 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.
Harry Senate
- Played by: Nicky Katt
A 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.
- 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 "Chapter Twelve", 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.Scott: 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.Scott: You think this is funny, Mr. Senate?
- Pragmatic Hero: He employs very questionable methods to help his students. Unsurprisingly, he often clashes with Steven and Scott over this.
- Put on a Bus: In early Season 3 due to PTSD.
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.
- 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.
- Bunny-Ears Lawyer: Steven even notes that, while Marla can be erratic, she has leadership skills.
- Hot-Blooded: Marla is a very passionate and emotional woman.
- Sassy Black Woman: 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.
- Domestic Abuse: In Season 3, she was revealed to have been abused by her husband. The following season, she confronts her reformed husband.
- History Repeats: 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.
- Hot Teacher: She even topped a student poll about teachers students wanted to sleep with most!
Louisa Fenn
- 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.
- Chuck Cunningham Syndrome: 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.
- Servile Snarker: She liked to make witty comments.
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.
- Butt-Monkey: He was often the center of Sheryl Holt's website cartoons.
- Meaningful Name: Milton Buttle is often the butt of people's jokes.
- Put on a Bus: Midway through Season 1.
- The Bus Came Back: For only a few minutes in "Chapter Fifteen".
- Teacher/Student Romance: With Lisa in Season 1. He gets fired when the relationship is discovered.
Kevin Riley
- Played by: Thomas Mc Carthy
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.
- The Pirates Who Don't Do Anything: He's stated to be a teacher, but we don't ever see him teaching anything.
- Put on a Bus: Midway through Season 1.
- The Bus Came Back: In "Chapter Eighteen". He's never seen again after that.
Tina Knowles
- Played by: Alexondra Lee
A phys ed teacher.
- Ambiguously Gay: Lauren suspects she's a lesbian due to a look she gave her.
- 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.
Jenna Miller
- Played by: Gina Philips
An attractive English teacher who once had a relationship with Harry Senate.
- Hot Teacher: Is she ever! Scott 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.
- Teacher/Student Romance: 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.
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.
- 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.
Danny Hanson
- Played by: Michael Rapaport
A social studies teacher who begins teaching at Winslow High in Season 2.
- Cool Teacher: 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.
- Deadpan Snarker: He was hardly ever without a wisecrack.
- Former Teen Rebel: It's stated in one episode that he stole a car when he was a teenager.
- Hot-Blooded: A trait he shares with Marla. In fact, they're able to make peace with one another over this in Season 3.
- 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.
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.
- 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.
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.
- Chuck Cunningham Syndrome: Disappears after the third season.
- Cool Teacher: 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.
- Love Triangle: Becomes involved in one with Dave Fields and Ronnie in Season 3.
- Suspiciously Similar Substitute: He's basically Harry Senate without any emotional trauma.
- Well-Intentioned Extremist: Just like Harry. He even dissects a corpse in his classroom, which unsurprisingly lands him in hot water with Scott.
Colin Flynn
- Played by: Joey Mc Intyre
An English teacher who begins teaching at Winslow High in Season 3.
- Chuck Cunningham Syndrome: Disappears after the third season.
- Cool Teacher: He's introduced wearing hip clothes, using a casual vocabulary with students, and letting students address him by his first name.
- 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.
Kimberly Woods
- 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 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.
Carmen Torres
- Played by: Natalia Baron
A 21-year-old physics teacher who enters in Season 4.
- The Alcoholic: She admits she was one.
- Chuck Cunningham Syndrome: 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 and Harvey even comes onto her in his Quest for Sex to stave off Alzheimer's.
Winslow High Students
Jason Harrelson
- 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 he's smarter than he lets on.
- Chuck Cunningham Syndrome: He isn't seen again after "Chapter Five."
Dana Poole
- 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 Scott to back down from getting a urine sample from her by threatening to reveal their kiss.
- Teacher/Student Romance: She and Harry briefly date sometime after she graduated from Winslow and began attending college.
Anthony Ward
- Played by: John Francis Daley
A nerdy student who was bullied. He later started writing about killing his tormentors in his journal, which was discovered.
- Butt-Monkey: He was often a target for bullies.
- Idiot Ball: If Anthony had kept his journal at home in the first place, he ultimately wouldn't have been transferred to another school.
- Nightmare Fetishist: He thinks it's fun to imagine his bullies dead and wrote his fantasies in his journal.
- 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.
Sheryl Holt
- 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 Scott.
- Knowledge Broker: She had a close eye on current events taking place in the school. Steven and Lauren even approached her for info at separate points.
Malcolm White
- Played by: Zachery Ty Bryan
A bully who torments Anthony Ward.
- The Bully: Textbook example.
- Too Dumb to Live: Yeah, Malcolm, hover close by the principal while he's talking to the kid you've been terrorizing.
Jamal Crenshaw
- Played by: Edwin Hodge
A student in the Dungeon classroom.
- Apathetic Student: 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.
- Chuck Cunningham Syndrome: The last we see of him, he's serving time in prison.
- 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.
Lisa Greer
- Played by: Bianca Kaijich
A student who begins a relationship with Milton Buttle that results in him being fired.
- Karma Houdini: 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.
Jeremy Peters
- 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.
- Chuck Cunningham Syndrome: 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.
- Madden Into Misanthropy: 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.
- Straight Gay: Doesn't show any Camp Gay 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.
- Everything Is Racist: 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.
- Rousing Speech: Gives one in the Season 1 finale during the graduation ceremony.
Brooke Harper
- 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.
- Age-Gap Romance: She's a teen who briefly dates a 27-year-old insurance adjuster, 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.
- Soapbox Sadie: She gets involved in the student protest in the Season 3 premiere.
Marcie Kendall
- Played By: Cara DeLizia
- Servile Snarker: Much like Louisa.
- Teen Pregnancy: Midway through Season 3, she becomes pregnant by her boyfriend.
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.
- 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 Scoop: She also worked as a reporter for the school's TV station, and is played by the attractive Courtney Peldon.
- Foil: Her disorganized behavior to Scott's strictness.
- Servile Snarker: To Scott, out of all people. And most importantly, he allows her to do that and even picks up some of her Simpleminded Wisdom.
- Teacher/Student Romance: Had a crush on Colin Flynn in Season 3 and was thus devastated to learn that he was having an affair with her mother.
Other Characters
Walter Harrellson
- 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: He's implied to be emotionally abusive to Jason who mentions to Lauren that Walter calls him "dumb."
- Adults Are Useless: 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 blaming the teachers for Jason's failures.
- "Angry Black Man" Stereotype: 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.
- Jerkass: He has a combative and aggressive demeanor.
- Never My Fault: Blames the faculty for his son's academic failures rather than completely accept his own role in Jason's apathy towards his studies.
- Perpetual Frowner: Pretty much his default expression.
Marsha Shinn
- 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.
- Chuck Cunningham Syndrome: 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 right to her face that he considers her to be one of many problems he has when it comes to running Winslow.
Louanna Harper
- 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.
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.
- Love Triangle: Becomes involved in one with Ronnie and Zach in Season 3.
- Obstructive Bureaucrat: Steven even notes this in his first appearance.Steven: Mr. Fields, you are not here to help us; you are here to help the Mayor get re-elected.
Charlie Bixby
- Played by: Dennis Miller
An 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.
- Chuck Cunningham Syndrome: 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.
- 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 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: [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?
- Third-Person Person: He had a habit of repeating his own name.
