- Fridge Brilliance: Giving Judge Ford clues that she interprets as offensive may actually have been a deliberate ploy to keep her from having her clues researched by outside agents, the way she'd had the heirs and Westing investigated. Because their content had racist overtones, hiring someone else (probably someone white) to track down possible meanings for SKIES AM SHINING BROTHER would've been terribly embarrassing for both parties.
- Hilarious in Hindsight: Judge J. J. Ford, the first black person (and first woman) elected to a state judgeship, went to Columbia and got her law degree at Harvard. In the epilogue, it's revealed that she's appointed to the U.S. Supreme Court.
- Magnificent Bastard: Sam Westing pretty much fits all categories.
- Jerkass Woobie: Crowe. She's a grumpy, anti-social woman who lives with the guilt of pushing her daughter towards a marriage that caused the daughter to commit suicide. This is shown to still effect her, as evidenced by her repeated desire to comfort Angela (who is in the same position). Near the end of the game, she's perfectly accepting of the fact that she was just named as Westing's murderer and names herself as the "answer" to the game despite being able to walk free if she kept quiet (no one else was willing to name her). The reason she did it? So she could donate half of her winnings to the soup kitchen she worked at and the other half to Angela, so Angela would be free to go to medical school.
- Values Dissonance: The portrayal of the Hoos shows a very '70s view of Asians.
- The use of the words "retarded" and "mongoloid," which weren't considered offensive at the time.
- Also, although it is only mentioned in passing and doesn't really become relevant until what Ford does for him during the "Where Are They Now?" Epilogue, Jake Wexler is a bookie—and as revealed below under Grace's Woobie entry he's a Jew.
- The Woobie
- Aspiring writer/chessplayer and dutiful son Theo Theodorakis, whose primary duties are to his parents' business and his ill younger brother. His infatuation with Angela goes unrequited, and he later becomes a suspect in the Westing House bombings after accidentally blowing up his high school chemistry lab. The fact he becomes a well-respected reporter, a published (if not particularly successful) author, and marries the now-hot-and-soon-to-be millionaire Turtle takes some sting out of it.
- Angela could also fit. She spends the book dealing with her mother making a huge fuss out of the upcoming wedding, which Angela doesn't even want to do. She doesn't seem to have many friends and her bridal shower is full of women she doesn't even know. And she feels she can't just call off the wedding because she doesn't want to hurt her fiance or let her mother down. Eventually, she is so stressed that she starts setting off bombs to try to let off steam. In the process, she accidentally injures her partner (who is possibly her first close friend) and blows up her own face to keep her sister from being caught in an explosion. Oh, and what she originally put down as her position in life? "None".
- On the other side of the coin, Turtle has to deal with the fact that she is clearly her mother's Unfavorite.
- Grace Windsor Wexler herself has Jerkass Woobie tendencies. A great deal of her unflattering, elitist, and prejudiced behavior is driven by the trauma of having been disowned by her parents for marrying a Jew — thus being brutally punished for the most open-minded thing she ever did.
- Sun Lin Hoo. She spends the first part of the book completely homesick and unable to speak any English at all. It's implied that this is the case because no one speaks to her besides her husband. She becomes so desperate to return to China that she steals various items, but then feels incredibly scared and guilt-ridden over her actions.
- Flora Baumbach becomes this late in the story, when it's revealed that her daughter whom Turtle'd envied had been mentally challenged, and her husband may have deserted them because of this.
- Subverted with Chris, who would be a pitiable character if not that he's absolutely thrilled to be a part of something as exciting as the Westing Game, hence is too cheerful to be a Woobie.
- Sydelle Pulaski. She seems to be friendless, is overlooked by most of the residents of Sunset Towers, and is lonely enough that she fakes having a wasting disease so she can have some attention. She's later injured in a bomb blast, which turns out to have been set off by her own partner (not that Angela was expecting anyone to get hurt in it - Sydelle being in the area was completely accidental). To top it all off, Sydelle wasn't even supposed to be one of the heirs! Westing had planned for a woman named Sybll Pulaski (a friend of his wife's) to be included and Sydelle got her invitation by mistake. The game was possibly the most interesting thing she was ever included in and she wasn't even supposed to be there.
- They Changed It, Now It Sucks: At least some fans of the book had this reaction to the picture.
- The Untwist: Viewers who notice that Barney Northrup, Sam Westing, and Sandy McSouthers all share an actor, Ray Walston, might beat Turtle to realizing that they're all the same person.