Characters: Boston Public

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    Winslow High Staff 

Steven Harper

Played by: Chi McBride

The principal of Winslow High who has to deal with the wacky antics of his faculty.
  • 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 Harper is (usually) benevolent, calm, reasonable and well-liked.
  • Team Dad: To the rest of the faculty.

Scott Guber

Played by: Anthony Heald

The assistant principal of Winslow High, known for being very strict, formal, and authoritarian with both students and teachers.
  • Don't You Dare Pity Me!: 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 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 found dead.
  • Hypocrite: In Season 2, he chastises Lauren to her stern behavior, not acknowledging he himself is quite strict with both students and staff.
  • Informed Judaism: 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.

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.
  • Brother Chuck: 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.

Harvey Lipschultz

Played by: Fyvush Finkel

An elderly History teacher, known for being a bigot and completely unaware of how his racist 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.
  • 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.

Harry Senate

Played by: Nicky Katt

A teacher 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 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.
  • 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.

Marla Hendricks

Played by: Loretta Devine

A 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.
  • Hot-Blooded: Marla is a very passionate and emotional woman. Guber even notes that this is her biggest flaw and the reason why 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.

Marilyn Sudor

Played by: Sharon Leal

A teacher who also led the student choir.
  • Hot Teacher: She even topped a student poll about teachers students wanted to sleep with most!

Louisa Fenn

Played by: Rashinda Jones

Steven and Scott's secretary. Appears in Seasons 1 and 2. Disappears from the show starting in Season 3.
  • 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 in Season 2 that her father is black and her mother is white.
  • What the Hell, Hero?: Sums up Steven's response to the above trope.

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 ends up fired for it. Appears only in Season 1.

Kevin Riley

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 just replies "Go to Hell, Steven" and proceeds to deliver a "Reason You Suck" Speech.

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 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.

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.

Zach Fischer

Played by: Jon Abrahams

A teacher who enters in Season 3. He himself used to be a student at Winslow High years ago.

Colin Flynn

Played by: Joey McIntyre

Kimberly Woods

Played by: Michelle Monaghan

  • Hot Teacher: A male student even ogles her legs and a female student becomes attracted to her.

Carmen Torres

Played by: Natalia Baron

  • Gratuitous Spanish: Steven calls her on teaching her Physics class in Spanish.
  • Hot Teacher: She even gets mistaken for a student in her very first episode.

    Winslow High Students 

Dana Poole

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.

Jamal Crenshaw

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.
  • 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 isn't interested in attending college.

Jeremy Peters

Played by: Kaj-Erik Eriksen

A 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.
  • Straight Gay: Doesn't show any Camp Gay behavior despite being bisexual.

Brooke Harper

Played by: China Jesusita Shavers

Steven's rebellious teenage daughter who gets kicked out of her private school, leading to her attending Winslow High.

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.
  • 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.

    Other Characters 

Marsha Shinn

Played by: Debbi Morgan

The superintendent of schools in Boston.
  • Bad Boss: They call her the "Dragon Lady" for a reason.
  • Jerkass: She's very unpleasant. Why do you think she's called the "Dragon Lady"?

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.

Charlie Bixby

Played by: Dennis Miller