Characters from Pleasantville include:
Jennifer's Twin Brother. David is a socially awkward teenage son of a divorced mother and a fanboy of the 50s sitcom Pleasantville, which he uses to escape what he views as an imperfect life. After bickering with Jennifer over the remote causes them to get transported into the world of Pleasantville, he becomes Bud Parker. The son of the titular Parker family. He is very knowledgeable about even the most obscure references, which he uses to try to get through the show while playing Bud.
- Adorkable: In the real world he's a complete outcast and only has one friend. But when transported into Pleasantville he was able to get along just well with the townspeople due to his knowledge of the show. It crops up every now and then when Margaret takes an interest in him.
- Ascended Fanboy: He always wanted to live life like Pleasantville, so the trip into the world is a dream come true to him.
- Beware the Nice Ones: His rivalry with his sister aside, he is a nice person. However harm Betty and you'll get punched so hard, you'll bleed red in a black and white world.
- Face Heel Turn / Heel Face Turn: When they first go into Pleasantville, David is just as shocked as Jennifer in that they became Bud and Mary Sue. However whilst Jennifer didn't want to play her role and rather mess things up to add excitement on the show, David insisted on playing his role in an effort to keep the show in balance until they can get out of here. It goes further on the former when he finds he excels in sports and feels in his element on the show. However when he notices how the citizens that turned color are being treated by the still monochrome citizens, as well as some Monocrhome and Color Students alike curious about "What's outside of Pleasantville", he changes his tune and helps them out, even becoming their unofficial leader against Big Bob.
- The Leader: While the color change didn't happen until Jennifer started to shake things up, once David turned Technicolor he became the unofficial leader of the group. Best seen when he is the one that reads aloud the Pleasantville Code of Conduct, encourages the teens to dance to forbidden music and even helps Bill spearhead the mural.
Jennifer/Mary Sue Parker
David's twin Sister. Jennifer is the popular promiscuous teenage daughter of a divorced mother. In her attempt to impress her recent date, she bickers with David over the remote for the main TV. Wanting to watch an MTV concert with said date. This in turn causes the two to get transported into Pleasantville. Where she becomes Mary Sue Parker. The daughter of the titular Parker family. Unlike David, she has no knowledge of the show and relies on David to get to know the characters. She was initially bummed out, until she shows interest in Skip Martin. The love interest on the show. Her attempts to shake things up on the show are what kick start the events that cause the monochromatic society to slowly transition into technicolor.
- Character Development: She starts off as a promiscuous teenager who tries to shake things up in Pleasantville. But over time when she discovers the once blank books fill in with text, she uses it as an opportunity to turn her life around and become an academic.
- Gag Boobs: When she prepares for her date with Skip she wears a bra that makes her breasts look bigger than they actually are. She remarks that she could kill a guy with them.
- Naive Newcomer: She has no knowledge of the show Pleasantville and often relies on David just so she can know the names of the characters she interacts with. Everything else she just wings and as a result inadvertently causes the town to slowly turn into technicolor.
- Spanner in the Works: Her actions are the first thing that causes the normally monochrome citizens of Pleasantville to turn color.
The matriarch of the Parker Family in the Pleasantville TV show. A house wife who at first was content with everything the way it is, but when Jennifer takes Mary Sue's place as her daughter, she is the first in the family to be taught things beyond pleasant. Which in turn makes her one of the first citizens of Pleasantville turn technicolor.
- A Date with Rosie Palms: When she speaks to Jennifer/Mary Sue about what goes on in lover's lane. Jennifer explains among most things sex. Further explaining the birds and bees to her. When Betty fears that George wouldn't want to try it with her, Jennifer offers this trope as a solution to that. Later that night she puts the trope into play and causes an orgasm so big that it causes a nearby tree to catch fire.
- Don't Look At Me: Played with, when she turns technicolor, it was during a time when Big Bob makes George a member of the Pleasantville Chamber of Commerce, to celebrate George tries to ask Betty to bring her famous hors d'oeuvres. Getting no response, David/Bud goes to check on her finding out what happened. She doesn't want George to see her like this, so David, using make-up, covers it up to help her out.
- Doting Parent: Before and after her change, never stopped her from trying to be a good mother to David/Bud and Jennifer/Mary Sue. Bud especially since, he was able to help her out of two instances of trouble. Even when he decides to leave, she packs him a lunch and hands him his letterman sweater.
- Ms. Fanservice: Bill seems to believe her to be this trope as he went so far as painting a nude mural of her after they spent the night together. It takes a dark turn when a bunch of monochrome teens harass her over the mural.
- Supreme Chef: Taken up to eleven in this one. During their first time in the Parker house, David/Bud and Jennifer/Mary Sue, discover a huge pile of breakfast goods on the table. Enough to feed an army.
- Your Cheating Heart: A less negative example. Betty, still wearing make-up stops by Bill's soda shop out of curiosity over his technicolor Picasso Inspired Santa mural. He explains to her that David/Bud, gave him an artbook to inspire him and they discuss the meanings of the paintings. When Bill notices that Betty is Technicolor, he helps her uncover it. They end up spending the night together making love and painting. More or less out of passion that he sees her for who she is underneath and not the monochrome her husband expects. It's also implied in the end that she may continue her relationship with Bill.
The Patriarch of the Parker Family. A man who's life is composed of formula and routine. When Jennifer/Mary Sue shakes up the status quo, George often reacts to the changes that follow with confusion. Wondering where everything went wrong.
- And Then What?: He's the first to ask that when Pleasantville goes full technicolor.
- Catch Phrase: "Honey, I'm home."
- Doting Parent: Much like his wife Betty, he tries his best to be a good parent to David/Bud and Jennifer/Mary Sue. When Bud expresses his worry over Mary Sue, George tries to reassure him the only way a sitcom dad can.
- Heroic BSOD: When he comes home to find no wife, no lights on and no dinner, he becomes confused wandering in the rain wondering where the latter is.
George: Where's my Dinner?
- Nice Guy: Despite the changes going around, George still tries to be nice to his family and friends. When David/Bud goes to jail for the mural, he visits him and offers him food.
- Token Good Teammate: Within the Pleasantville Chamber of Commerce, he is this. While he does participate in the meetings, the trial and even contributes to the Pleasantville Code of Conduct, he doesn't hold anything personally against his kids who rebel against the chamber.
Notable Pleasantville Citizens
The Mayor of Pleasantville and head of the Chamber of Commerce. He serves as the closest thing to a primary antagonist. While he comes across as nice and laid back, underneath he's stubborn to the status quo that he's willing to do anything to keep it that way.
- Affably Evil: Despite being the antagonist, he's a very pleasant person to talk to. Very stoic and rarely loses his cool. Often trying to solve things in a peaceful manner.
- Big Bad: The closest to one in a movie. As mayor of Plesantville he serves as the main obstacle against Jennifer/Mary Sue and David/Bud, along with the technicolor citizens.
- Even Evil Has Standards: He despises violent solutions to the problems he addresses and the main reason he develops the Plesantville Code of Conduct is to avoid violence on both sides.
- Load-Bearing Boss: While it's not quite certain as the people and objects were already turning Technicolor, Bob fleeing may have caused the whole town to turn technicolor.
- Not So Stoic: While he tries to keep stoic in the tone of his voice, there are several scenes where he visually shows signs of his stoicism fading. An example being his bitter look when he notices the women going in the library monochrome and coming out technicolor.
- Pet The Dog: Before they become enemies, Big Bob awards Bud for heroism when the latter puts out the first fire of Pleasantville.
- Villainous Breakdown: Big Bob has an epic one that causes him to finally turn technicolor. When Bud shows him through Betty's mirror, he flees in shock never to return.
A soda shop owner and Bud's boss on the show. When David/Bud accidentally shows up late for work, Bill starts to question his purpose in life and becomes one of the few citizens of Pleasantville to want to get out of the status quo of things.
- Benevolent Boss: He doesn't hold it against Bud if he shows up late for work or abandons his post. The latter of which even causes him to take more initiative and finish the jobs that are usually assigned to Bud. Something he rushes home to tell Bud in immense pride.
- Heroic BSOD: When he starts to question the status quo of his life and job, it causes him to shirk his work and go into an existential crisis.
- Hidden Depths: Bill is a good painter and in every Christmas Special of the show, he's often allowed to paint a different holiday themed mural in the window of his shop. David/Bud, fearing aspirations like that would destroy their universe, tries to discourage these depths. Only to relent later on and give him a book on art. Which inspires him to do his interpretations of various artists such as Pablo Picasso.
- Intergenerational Friendship: Despite both being an adult and teenager respectfully, Bill values his friendship with David/Bud. Which is likewise returned by Bud. David even goes the extra mile, when he hands him an art book to inspire him into painting.
- Nice Guy: One of the few members of Pleasantville to be genuinely nice rather than be strictly pleasant. So nice, that even after turning Technicolor, was willing to suppress his art in fear it has hurt people.
Captain of the Pleasantville Basketball Team and Mary Sue's love interest in the show. Also one of Bud's friends. Jennifer introduces the world of sex to the town through her encounter with him.
- Face Heel Turn/Heel Face Turn: When the town starts turning Technicolor, he is among the monochrome citizens trying to bring things back the way they were. In an attempt to burn Jennifer's/Mary Sue's book, he gets kicked in the groin for his troubles. However in the end he's among the last of the citizens turning technicolor, meaning whatever feelings he had as a monochrome have been washed away by Bud's speech.
- OOC Is Serious Business: When David/Bud initially tries to talk him out of dating Jennifer/Mary Sue, Skip throws his basketball at the net in anger. Instead of making a perfect shot, it bounces off the rim and rolls across the court amongst panicking players. Their coach even warning them not to touch the ball. Prompting Bud to try to talk Mary Sue into going out with Skip to fix things.
- Spotting the Thread: Skip is the first to see the changes in Pleasantville. After having sex with Jennifer/Mary Sue, he spots a rose in a garden that is red among the monochrome.
A cheerleader and David/Bud's Love Interest. In the show she was originally meant to be the Love Interest of a boy named Whitey, upon witnessing David's heroic act in putting out the fire, she shows interest in him instead.
- Adorkable: When she first tries to gain interest in David/Bud, she's shy and soft spoken.
- Interspecies\Interracial Romance: It starts out as the former as David/Bud is from the real world and Margaret is from the world of fiction. Then it turns into a subtle version of the latter when David is still Monochrome while Margaret has turned Technicolor.
- Star Crossed Lover: With David/Bud. When David finally has to go home to the real world it's left ambiguous to whether or not Margaret sees him again.
A minor character on the show. While little is known about him, it's implied he was meant to be the love interest of Margaret Henderson. However when Margaret shows more interest in David/Bud, he changes into a bully, becoming a secondary antagonist.
- The Bully: Becomes this when Margaret show interest in him.
- Fantastic Racism: Is not too subtle referring to technicolor people as "Coloreds"
- Oh Crap: When he and his gang try to hassle Betty, David/Bud punches him. Not only causing him to bleed, but his blood turning red. This on top of seeing Bud turning color offscreen causes him to flee.
- Back to Pleasantville