Chief Chilly

“You there with a mustache! I am the king of cold, Chief Chilly. I lock up anyone who challenge the superiority of my 'stache. In fact, I locked up one such fellow just the other day. Hmm.What a sad, mangy mustache you've got there. It hardly seems worth it to destroy you. With 'stache like that, you're clearly the sidekick ,not the star. But I'm between meetings now, so I might as well. In the battle for the best mustache. I'll win, hairs down, ha ha ha! Bring it on, peach fuzz!”

—Chief Chilly, Super Mario 64 DS

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Chief Chilly being knocked of the edge by Luigi.

Chief Chilly is a large Big Bully made of ice and apparently the leader of all Bullies. He first appeared in Super Mario 64 DS, the Nintendo DS remake of Super Mario 64. Like several other bosses of Super Mario 64 DS, Chief Chilly takes great pride in his mustache. Bowser hired him to trap the heroes of the game along with his other minions.

Presumably, at the beginning of the game he ambushed Mario, Luigi, and Wario, along with Bowser, Goomboss, and a Big Boo (presumably King Boo), and was put under the control of Wario or he chose to take Wario as he made fun of his mustache of which both look like each other. Then Luigi came to Wario's rescue and was forced to battle the monstrosity. Despite being the second weakest of the four he managed to beat him and push him off the iceberg and the key was given to Luigi. He went home to restyle his mustache and to get a rematch someday.

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Chief Chilly in Mario Kart DS.

In Mario Kart DS, Luigi must battle Chief Chilly in Level 6 of Mission Mode. Like the battle with Big Bully, Luigi must push Chief Chilly off his platform and into the water. However, Chief Chilly must be pushed off three times instead of one, and becomes stronger and trickier after each time he is pushed off. In fact, after the second time he falls in the water, Chief Chilly will be able to Jump over Luigi's boost attacks. To defeat him, Luigi had to attack Chief Chilly from the side, where the boss couldn't see him. Its possible that this could've been his rematch but it is not known if the Mario Kart games are in continuity or at least the mission mode.