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Winchester University

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Armstrong/Parker House

     Sam White 

Samantha "Sam" White

https://static.tvtropes.org/pmwiki/pub/images/dwp_sam_white.png
Portrayed by: Tessa Thompson (film), Logan Browning (series)

  • Ambiguously Brown: In the film, Sam gets this reaction repeatedly and resents it. Gabe goes so far as to accuse her of playing up a "Tragic Mulatto" front. Sam herself identifies unambiguously as black, and does not once question, deny, or attempt to hide her own blackness. In fact she gets accused of overcompensating due to this. Averted in the series, where she's way more open about her mixed background, and makes no effort to hide it.
  • Arson, Murder, and Jaywalking: Among the criticism towards white people that Sam makes on her radio show are touching her hair without asking, dating a black person to piss off your parents and... dancing.
  • Black Gal on White Guy Drama: Sam is secretly having sex with a white guy, Gabe, at the beginning of the series. After she's outed, this doesn't go down well with her friends, particularly since she wrote against "dating the oppressor". Gabe receives a less than warm welcome when she brings him to TV night with the black students.
  • But Not Too White: Sam does not once address her white father until the end of the movie. Averted in the series, however.
  • Category Traitor: She wrote an editorial titled "“Don’t Fall in Love With Your Oppressor: A Black Girl’s Guide to Dating at Winchester,” is seen as this by some of the black students in Season 1 when her relationship with Gabe (a white person) becomes public.
  • Dating Catwoman: He's certainly no villain, but building racial tensions and Sam's very vocal position in them leads her to hide her relationship with Gabe, even antagonizing him in public.
  • Decoy Protagonist: Sam is this. While her rhetoric is both insightful and forceful, she accomplishes very little of substance compared to Lionel, who plays pivotal roles multiple times. And while she does get a significant amount of focus and development, so do the rest of the cast.
  • Friends with Benefits: Sam and Gabe's relationship starts this way, but quickly becomes a full romantic relationship.
  • Half-Breed Discrimination: Sam mentions that people insult her sometimes over being mixed race in the series. It gets much worse with the internet troll AltIvyW in Season 2.
  • Ironic Name / Meaningful Name: Sam White identifies strongly as being black, despite being mixed race.
  • Malcolm Xerox: Sam serves as a female version of this in the film, though she mellows by the ending. In the series, it's more prolonged.
  • Maligned Mixed Marriage: AltIvyW, the internet troll in Season 2, horribly insults Sam's dad (who's white) for having Sam with her black mother. This causes her to cry, and inspires Sam in taking up anti-racism again.
  • Mistaken Nationality: Reggie apparently mistook Sam for Puerto Rican at first.
  • Hypocrite: She wrote an editorial denouncing black women dating white men, but is secretly dating one herself. Additionally, she implies she gets hit with racism from both sides of the fence due to being mixed race, but she focuses exclusively on white-to-black racism, ignoring the black people who scorn and mock her for being half white.
  • Mixed Ancestry: Sam openly mentions she's biracial to her friends in the series, but doesn't in the film.
  • Never Got to Say Goodbye/Parting Words Regret: Though Sam knew her father’s health wasn’t great, she didn’t know how bad it was or that he had undergone two surgeries before dying. In their last conversation, she cut it off early, because he was cautioning her against spending too much of her emotional energy fighting others. Sam is wracked with guilt that this was their last conversation until she found a last letter from him.
  • Open Mouth, Insert Foot: When Sam gets a caller on her radio show who disagrees with her aggressive perspective on campus police pulling gun on a Reggie at a party, she accuses him of being unaware of his white privilege - only for the caller to reveal that he's actually black while they're still both on the air.

     Troy Fairbanks 

Troy Fairbanks

Portrayed by: Brandon P. Bell

  • Black Best Friend: Troy attempts to become this for Kurt, but he's able to see through it.
  • Broken Ace: He's very much the Big Man on Campus, beloved by majority of the Student Body. It quickly becomes apparent during his spotlight episode that his father puts an insane amount of pressure on him to be the model black student, to the point that Troy resorts to drugs to help cope with the stress.
  • Missing Mom: In the film, his mother is unmentioned and never seen. It's revealed in the series she left when he was young.
  • Mr. Fanservice: He's the resident beefcake of the film and series. He has about two sex scenes with Coco and later Nieka Hobbs in Chapter III, along with a shower scene showing his bare ass.
  • Really Gets Around: If Lionel's POV is accurate going by the incessant female moans, Troy has a lady over every night of the week.
  • Role Reprisal: Brandon P. Bell is one of the only actors from the film to reprise their role in the series.
  • "Well Done, Son!" Guy: Troy structures his entire life around his father's approval. Unlike in the film though, he realizes it made him into a puppet for the Hancocks and violently rejects it.
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     Lionel Higgins 

Lionel Higgins

Portrayed by: Tyler James Williams (film), DeRon Horton (series)

  • Author Avatar: For Justin Simien.
  • Black and Nerdy: Lionel. He dressed as Geordi LaForge at a high school dance, causing some mockery from other black guys.
  • Coming-Out Story: Lionel, unlike the character in the film, is still questioning his sexuality at the beginning of the series. He grows increasingly sure he's gay before finally coming out to his roommate Troy (who he finds attractive, though the latter is very straight, and he doesn't tell him this). Troy accepts it easily.
  • Disappeared Dad: Lionel's dad died before he was six. Even before this he wasn't around, due to having a secret other family he wouldn't leave.
  • Gosh Dang It to Heck!: Lionel always uses terms like "malarkey" and "hooey" rather than actual swear words.
  • Important Haircut: Lionel has Troy cut his afro after at last admitting to himself that he's gay.
  • Straight Gay: Lionel... to the straight characters, anyway. At the very least, he's not outwardly flamboyant.
  • Twofer Token Minority: Black and gay.

     Coco Conners 

Colandrea "Coco" Conners

https://static.tvtropes.org/pmwiki/pub/images/dwp_coco.png
Portrayed by: Teyonah Parris (film), Antoinette Robertson (series)

  • But Not Too Black: In the film, Coco invokes this for herself when joking that white girls' tans are getting darker than her own skin tone, "which...isn't that dark...". Coco's character arc is also very much about the nefarious effect of colorism in society; Coco tries very hard to fit within the white standards of beauty as revealed by her use of colored contact lenses (in the film) and weave, being anxious about exhibiting her natural hair and having a predominantly white Girl Posse. This explains her fallout with her friend Sam who, in contrast, tries to erase her white heritage and to emphasize her blackness.
  • Dark and Troubled Past: Coco in Episode 6 of Season 1 reveals she grew up on Chicago's South Side and watched friends and family get shot and killed, harboring the feeling that she could've done something to save them.
  • Ghetto Name: Coco's real name is Colandrea.
  • Good Girls Avoid Abortion: Played with. She is deeply conflicted about the decision, but ultimately decides to have one. But when she goes to the abortion clinic with Kelsey, she decides against it, leaves Winchester, ultimately becomes a lawyer, and raises her daughter (with Troy’s apparent help), who herself gets into Winchester. But it’s then revealed to be a Daydream Surprise, and Coco instead goes through with the abortion. She obliquely refers to the abortion throughout the rest of Season 2, but it’s not shown how much it truly affected her.

     Reggie Green 

Reggie Green

Portrayed by: Marque Richardson

  • Green-Eyed Monster: Downplayed, but Reggie is clearly less than pleased at finding out Sam and Gabe are in a relationship. Ironically, Joelle is one for him, but never acts on it because of his clear attraction to Sam.
  • Role Reprisal: Marque Richardson is one of the only actors from the film to reprise their role in the series.
  • Therapy Is for the Weak: Reggie tries several methods to deal with his PTSD—sex, drugs, a Bible study—but refuses to see a therapist.

     Joelle Brooks 

Joelle Brooks

Portrayed by: Ashley Blaine Featherson

  • Adaptation Expansion: Joelle wasn't even given a proper name in the film. She's more of a character in the series.
  • Named by the Adaptation: She's credited as "Curls" in the film.
  • Role Reprisal: Ashley Blaine Featherson is one of the only actors from the film to reprise their role in the series.
  • Romantic Runner-Up: Joelle feels this way compared to Sam, especially when it comes to Reggie. Ultimately defied though, as Joelle and Reggie get together in the Season 2 finale.

     Kelsey Phillips 

Kelsey Phillips

Portrayed by: Nia Jervier

  • Adaptation Expansion: Kelsey wasn't even given a proper name in the film. She's more of a character in the series.
  • The Ditz: Kelsey, in some aspects. Following the blackface party, Kelsey successfully manages to get a therapy dog for herself because she told the counselor she would kill herself over the party. In addition, she was genuinely surprised that racism was still a thing that could happen. She actually does experience racism in the aftermath of the final episode where Sorbet is dognapped, with only a note reading, "Black girl, white dog, not on my watch" left behind, but is dismissed by virtually everyone in the room.
  • Hidden Depths: True about many of the characters, but Kelsey is a particular standout. In Season 1, she is largely portrayed as The Ditz, but she proves to be very caring and more aware of others than they are of her. She is especially there for Coco when Coco learns she is pregnant and chooses to get an abortion. Kelsey is also a lesbian, which Coco – and likely all the main characters – never realized, because she is (they are) so self-absorbed.
  • Lipstick Lesbian: She's gay and very feminine.
  • Named by the Adaptation: She's credited as "Coco's Friend" in the film.
  • Role Reprisal: Nia Jervier is one of the only actors from the film to reprise their role in the series.
  • Twofer Token Minority: She's a black lesbian.
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Other students

     Gabe Mitchell 

Gabe Mitchell

Portrayed by: Justin Dobles (film), John Patrick Amedori (series)

  • Demoted to Extra: Gabe goes from being one of the major characters of Season 1 to barely present in Season 2, except for Episode 8, when he and Sam address the events and causes of their breakup.
  • Friends with Benefits: Sam and Gabe's relationship starts this way, but quickly becomes a full romantic relationship.
  • Nice Job Breaking It, Hero!: Corresponding with the above N-Word Privileges, Gabe was the one to call on Campus Security in order to break up the ensuing fight. Gabe didn't predict that one of the security guards would pull a gun on Reggie however.
  • Out of Focus: In the second season.
  • Suspiciously Similar Substitute: In-universe. Gabe begins flirting with the new black woman in his film course in order to make Sam jealous.
  • Token White: He's the only prominent white character in the main cast.

     Silvio Romo 

Silvio Romo

Portrayed by: DJ Blickenstaff

  • Category Traitor: Silvio is a gay Mexican who has secretly become an alt-right Twitter troll, because of what he sees as Sam’s attack on campus free speech .
  • Face–Heel Turn: He has one after the Independent goes under, and he takes on the Secret Identity of @AltIvyW.
  • Mixed Ancestry: He specifically mentions that he's mixed Italian and Mexican-American.
  • Politically Incorrect Villain: @AltIvyW is revealed to be Silvio, who uses his new platform to lash out at Sam for "attacking" free speech and enabling privileged rich kids, no matter what their race or ethnic background... despite him being a gay Latino himself.
  • Walking Spoiler: In the second season.

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Outside Winchester

     Rikki Carter 

Rikki Carter

Portrayed by: Tessa Thompson

  • Category Traitor: She exploits this, because she knows white conservatives particularly value having a racial minority who agrees with them. She even maintains a fake feud with Carson Rhodes, a black liberal commentator, in order to up her book sales and speaking fees.
  • No Celebrities Were Harmed: She's very much reminiscent of conservative pundit Candace Owens, a black woman who staunchly criticizes liberals and the Democratic Party.
  • Not So Different: Rikki Carter tries to deliver one to Sam. Made all the more ironic that Tessa Thompson portrayed Sam in the film.
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