Shadows Over Loathing is a (slap)stick-figure adventure full of mobsters, monsters, and mysteries, set in a fantasy-horror version of the 1920s prohibition-era United States. You play as a paranormal detective following a trail of cursed artefacts in the hope of finding your missing uncle. Shadows Over Loathing stands out not only for its black and white stick figures but for its sense of humour, story, and character-based puzzle-solving.

Play consists of point-and-click exploration, where you choose something or someone that looks interesting to talk to or interact with it. To progress you need the right characteristics to match what you are trying to do. For example, have a Muscle score of 5 to push a boulder out of the way, or Stench Armour of 4 to go into a place that smells very bad.

To progress you use the items and equipment you find to change your stats. You can also eat food or drink a potion to gain a needed bonus temporarily. Collecting gear and consumables becomes an important way to continue exploring. In this way you traverse several maps worth of wacky locations, interacting with the characters and puzzles you find, and engaging in turn-based combats.

The result is a game about exploration and puzzles. Despite the fantasy horror setting, it's a light-hearted game that leans heavily on story, jokes and puns (almost every interaction provides some kind of story or joke).