Bosses of Tingle's Rosy Rupeeland

In Freshly-Picked Tingle's Rosy Rupeeland, bosses are discovered at the end of dungeons much like previous games in the Legend of Zelda series. These bosses appear inside giant chests that Tingle must also jump into. Unlike other enemies, bosses are battled in special ways and often give Tingle a health meter instead of a rupee meter; losing all of his health will dump Tingle back outside of the chest with a deduction to his funds.

Death Bug

Known as the Beetle Lord, the Death Bug is encountered at the end of the Hero's Shrine in Hometown Prairie. It is an enormous creature that spits out larvae and sparks to attack for it. Its weak point is an odd, humanoid face located between its eyes.

For this battle, Tingle is flying around the room via 9 balloons on his back, while Teddy Todo will run around the room and kill the offending larvae. Tingle must grab bombs from the bomb plants scattered around the room and toss them at the face three times to defeat the creature; however, if he loses all of his balloons, he will be thrown out of the chest.

After hitting the face three times, Teddy Todo will spring into action and hip-drop the weak point, finishing the bug off. Tingle and Teddy Todo can then collect the large rupee shards that were embedded in its body. Tingle will also receive the Metal Rupee after they leave the chest.

Captain Stalfos

Captain Stalfos is the leader of a crew of undead skeleton pirates whose hideout is located near Cape Treasure. Like his crew, he is a skeleton, though he is somewhat larger and wears a hook. He does not actually mean Tingle harm during their fight, but wants to turn him into a skeleton so he can join the crew as well.

Tingle and Captain Stalfos duel in a style similar to Punch-Out, without any actual boxing. The captain will hurl fireballs and swipe with his sword, which Tingle can jump over; doing so gives him an opportunity to counterattack the captain's face. Once Captain Stalfos is defeated, he explodes into giant Rupee shards and gives Tingle the Aqua Rupee after he leaves the chest.

Though Captain Stalfos refuses to accept Tingle into the crew, he does acknowledge him as a friend and offers him the Bone Ocarina. This proves useful later on when the crew is possessed by the remains of Death Bug's offspring. The captain's head is separated from his body and rampages in the lowest deck of their ship until Tingle arrives and separates the bugs from him with five simultaneous TNT explosions. As a reward, Captain Stalfos has the Bone Ocarina upgraded so that it can find and open the pirates' hidden treasure chests throughout the land.