Video summary

Gloom: Amber Benson, Michele Boyd, and Meghan Camarena (Strawburry17) join Wil on TableTop

Main summary

Key takeaways

Gaming

Game Storyline / Theme (The “World”)

  • Gloom is a darkly comic card game where each player controls a family of misanthropes—eccentrics like “Hemlock Hall” and “Dark’s Den of Deformity.”
  • The story is told through your turns: everything you do with cards is framed as a justification for horrible life events.
  • This session’s overarching “plot”:
    • families descend into escalating misery, often through death, calamity, and spite
    • rivals sometimes suffer “wrong” outcomes, which can even boost the wrong family’s misery score

Gameplay Rules Explained (How You Win)

  • On your turn, you can play three types of cards:

    1. Modifier cards
      • Negative modifiers on your own family to make them more miserable (good for you)
      • Positive modifiers on rivals’ families to make them happier (bad for them)
    2. Event cards
      • Cause special effects (including canceling actions).
    3. Untimely death cards
      • Used on characters who have negative self-worth
      • Remove them from the game and award points to the player who caused it
  • Scoring is “golf-like”:

    • You gain points for the dead family members
    • The lowest self-worth score wins (i.e., more miserable outcomes are better)
  • When a family has no characters left, the game ends and you tally the dead’s points.

Gameplay Highlights / Key Moments

Families and Characters Introduced

  • Amber Benson (Blackwater clan)
    • Old Dam, Angel (starry-eyed serial killer), Balthazar (unfaithful hound), Cousin Mordecai
  • Meghan Camarena / “Strawburry17” (Smythes)
    • Mr. Butterfield (butler), Lord Wellington-Smythe (duke), Lola (wild child), the Twins
  • Michele Boyd (Slogars)
    • Professor Helena Slogar (matriarch), Melissa Slogar, Lord Slogar, Grogar (teddy bear scamp)
  • Wil Wheaton (Darius Dark’s traveling circus)
    • Darius Dark (sinister ringmaster), Thumbelisa, Samson O’Toole (bearded man), Elissandre De Ville (illustrated lady)

Early Strategy Framing (What’s “Good” in Gloom)

  • Wil states the core winning concept:
    • Get characters to negative self-worth quickly
    • Kill them off (engineer misery, then use untimely death)
  • The group repeatedly jokes about the idea that stories justify the misery—so even deaths get elaborate comedic “lore.”

Major Deaths / Misery Events

  • Samson O’Toole (Wil’s circus)
    • Dies after drinking himself to death following the Twins being trapped and miserable
    • Framed as a “tragedy that inspires overdrinking”
  • The Old Dam (Amber)
    • Punished by mob justice after atrocities in her basement
  • The Twins (Meghan)
    • A chain of disasters, including:
      • trapped on a train and stung by wasps after an emergency-exit attempt
      • later celebrated in town while in the hospital, then targeted/beaten by beggars
    • Their increased popularity drives Professor Helena into despair, and she dies
  • Elissandre (Wil)
    • Experiences escalating harm (including injury/illness)
    • Eventually resolved through a complicated chain involving predators and bizarre outcomes
  • Wil repeatedly escalates comedic alliteration and escalating hazards:
    • mice → “menacing” circus mice, snakes, bears, and other absurd predator logic

Late-Game Turning Point

  • Wil claims that with the right setup—and by tracking negative self-worth and available death cards—he’s positioned to win.
  • However, the final scoring leads to unexpected results.

Strategies / Key Tips Emphasized

  • Engineer negative self-worth on your own characters quickly, then:
    • use untimely death cards at the right time to “cash in” misery for points
  • Use modifier/event cards to swing:
    • negative toward your family, positive toward rivals
  • Events can disrupt opponents
    • including cards that cancel actions
  • Narrative consistency matters (for this group):
    • the more coherent the comedic “why,” the better the table experience
    • mechanics still ultimately determine the points

Final Result (Who Won)

  • The match ended in a three-way tie for first, with:
    • Amber Benson: 70 points
    • Wil Wheatone: 70 points
    • Meghan Camarena: 70 points
  • Michele Boyd finished at 45 points
  • Wil notes it’s statistically rare to have a three-way win in a game like this.

Gamers / Sources Featured (Mentioned at the End)

  • Wil Wheaton (host)
  • Amber Benson
  • Michele Boyd
  • Meghan Camarena (Strawburry17)

Original video