Games like How to Win

In common: dark comedy, choose your own adventure, satire.

Kingdom of Loathing is a browser-based role-playing game. In common: breaking the fourth wall, satire, parody.

Abobo's Big Adventure is a freeware parody Flash game. In common: dark comedy, parody, free to play.

Corru.Observer is a hard sci-fi visual novel, point-and-click adventure about a contractor hired by an intelligence agency to hack into an alien biological… In common: dialogue trees, story rich, visual novel.

Make Cute Animal Friends in this 8-bit Gameboy-inspired adventure! In common: story rich, comedy, visual novel.

You have a problem: you're out of work, and the government is threatening to cut off your benefits. In common: choose your own adventure, free to play, visual novel.

In this darkly-humorous visual novel adventure, you’ll tackle fiendish puzzles, decide which very curious characters to trust, and compete in a pub quiz where… In common: choose your own adventure, free to play, visual novel.

Phonequest is a game about making friends online. In common: story rich, parody, comedy.

Cookie Clicker is a Javascript-based browser video game written by French programmer Julien Thiennot, better known as "Orteil". In common: breaking the fourth wall, free to play, comedy.

The Little Big Crisis is a financial simulation game based on the 2008 Great Recession where you become the chairman of the Federal Reserve and are tasked to… In common: political, satire, parody.