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Winslow High Staff
- Played by: Chi McBride
- Badass Teacher: Oh, yes, he gets his moments. He even slams a bully up against a locker in the pilot episode.
- Bald Black Leader Guy: He's bald, he's black, and he's the principal.
- Benevolent Boss: Most of the time. Just don't get on his bad side.
- Beware the Nice Ones: Steven is a polite and soft-spoken guy, but you do NOT want to get him angry.
- Former Teen Rebel: 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, he chastises Marla for her actions and refuses to give her his support. 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 snap once or twice, usually in response to the weird, 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 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. 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
- 10-Minute Retirement: In the penultimate episode of Season 3, he quits after a student he admired is found dead and he experiences a Heroic B.S.O.D., but come the season finale, 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 B.S.O.D.: He experiences one in the next-to-last episode of Season 3 after a student he admired is found dead.
- Hypocrite: In Season 2, he chastises Lauren to her stern behavior, not acknowledging he himself is the same way with both students and staff.
- Informed Judaism: Guber occasionally mentions he is Jewish, and is heard in the Season 2 finale speaking Hebrew.
- 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 woman 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, and this is after he was turned down for a Headmaster position at a private school.
- Played by: Jessalyn Gilsig
- 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
- Informed Judaism: He mentions he's Jewish on a few occasions, and is heard speaking Hebrew in a Season 2 episode.
- 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, 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
- 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: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.
- What the Hell, Hero?: 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.
- Played by: Loretta Devine
- 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
- Hot Teacher: She even topped a student poll about teachers students wanted to sleep with most!
- Played by: Rashida Jones
- 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.
- What the Hell, Hero?: Sums up Steven's response to the above trope.
- Played by: Joey Slotnick
- 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
- 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: Jeri Ryan
- 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
- 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
- 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
- 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
- Played by: Michelle Monaghan
- Put on a Bus: For her own safety.
- Played by: Natalia Baron
- The Alcoholic: She admits she was one.
Winslow High Students
- Played by: Sarah Thompson
- Hot for Teacher: She admitted to having feelings for Harry. They briefly date sometime after she graduated from Winslow and began attending college.
- Played by: John Francis Daley
- Butt Monkey: He was often a target for bullies.
- Played by: Edwin Hodge
- 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.
- What the Hell, Hero?: He gets chewed out by Harry in Season 2 for plagiarizing his college application essay (he bought it off the Internet).
- 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
- 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.
- Straight Gay: Doesn't show any Camp Gay behavior despite being bisexual.
- Played by: China Jesusita Shavers
- 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 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
- 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.
- Played by: Debbi Morgan
- 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. Why do you think she's called the "Dragon Lady"?
- Played by: David Conrad
- Love Triangle: Becomes involved in one with Ronnie and Zach in Season 3.
- Obstructive Bureaucrat: Steven even notes this.
- Played by: Dennis Miller