Chapters
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Shadows over Loathing is divided into 6 chapters in addition to a Prologue and an Epilogue, with each chapter focusing on an a new area. In order to progress through the chapters and subsequently the game, the player needs to complete the main quest in each area to find a particular cursed item that brings them one step closer to finding their missing Uncle Murray. Each chapter (except the epilogue) canonically occurs over the course of a day, beginning with the player waking up and ending with the player going to bed to have a dream that provides gameplay and story elements.
Chapters
Prologue
Focuses on making your way to Ocean City at the request of your Uncle Murray.
Main Quest: Find a full gas can. Find the terribly cursed fedora.
Chapter 1: Welcome to Ocean City
Focuses on the crime-filled streets of Ocean City.
Main Quest: Find the dangerous pocketwatch.
Chapter 2: The Spooky Forest
Focuses on the quiet and unnatural landscape of Crystaldream Lake.
Main Quest: Find the cursed compass.
Chapter 3: Back to School
Focuses on the halls and classes of S.I.T. Campus, Porkham.
Main Quest: Find the Librum Umbra Malum Ovilla.
Chapter 4: Swamped
Focuses on the dreary and harsh environment of The Big Moist.
Main Quest: Find Charles Wallace and the cursed key.
Chapter 5: Heartland of Darkness
Focuses on the smog-filled industrial land of Gray County.
Main Quest: Find the cursed sickle.
Chapter 6 (Finale): Sinister Enough for Government Work
Focuses on the soulless and sinister buildings of Government Valley.
Main Quest: Face The President of Shadows in The Black House and maybe save the world.
Epilogue (Resolution)
An overview of your achievements and the fate of the people and places you've encountered in your travels.
Dreams
At the end of each day (Chapter), the player has a dream. Some of these dreams offer the player gameplay elements like character classes, items, and unique perks/effects, while others offer story elements like lore, backstory, and plot progression.
| Chapter | Dream | Major event |
|---|---|---|
| Prologue | A Dream About School | Choose a character class |
| 1: Welcome to Ocean City | A Fitful Dream | Talk to your Nemesis |
| 2: The Spooky Forest | Another Fitful Dream | Your nemesis reports to their boss |
| 3: Back to School | Yet Another Fitful Dream | Dean Wormwood hopes his barrier will hold |
| 4: Swamped | A Disconcerting Dream | Vignettes of the President's life |
| 5: Heartland of Darkness | An Exceptionally Fitful Dream | Talk to the President |