One day, a 35 year old man hears a voice from the heavens:
"Are you tired of the daily grind? Come to the Western Pool!"
Venturing forth, he meets Uncle Rupee, a self-proclaimed "Rupee Master". Uncle Rupee promises the man that if he brings him Rupees and throws them in to the Western Pool, eventually he will gain access to Rupeeland, a magical realm that will grant his every wish and desire. The man agrees, and Uncle Rupee bestows upon him a magical costume and a new name: Tingle. It is Tingle's quest to get as much money as possible so that he can reach the gates of Rupeeland and find happiness.
Despite being a spinoff, Rosy Rupeeland shares little in common with its preceding franchise, The Legend of Zelda. Rupees mean everything in this game: they are both the money you barter with and how Tingle's health is measured, and ultimately, amassing rupees is your way to winning the game. Indeed, as Uncle Rupee tells you in the game's opening: "Rupees make this world go round." Many characters will not speak to you until you bribe them, and the amount of rupees you have to pay will to win their favor will vary from character to character. But you're never told how much you need to pay; you simply have to haggle until you find the correct price. Spend too many rupees, and you'll waste health. Spend too few, and the person in question will rebuke your requests for information. More rupees are acquired by completing quests, creating maps, or by mixing together materials to make and sell items.
Occasionally, your travels will lead you towards a dungeon. Inside of dungeons, body guards can be hired (for a price!) to help Tingle deal with tough enemies. Dungeons are finished with a boss encounter minigame where Tingle has to drop bombs on weak points of a monster. In addition to getting a massive amount of rupees for beating a boss, Tingle usually acquires a special type of Rupee.
Rosy Rupeeland is controlled using either the D-pad or face buttons to move Tingle. When Tingle moves close to an object he can interact with, you can tap it with the stylus to "look" at it. When Tingle gets in to a fight with an enemy, you can tap the "fight cloud" in order to turn the battle in Tingle's favor.
In 2009, IGN voted the game as having the scariest box art ever, ahead of Carmageddon for the Game Boy Color and Dr. Jekyll and Mr. Hyde for the Famicom/NES.