Chief Chilly is an icy, Bully-like boss. He has a giant, icy body with a giant, yellow crown, a giant, white mustache, and green shoes. He is the leader of all the Bully enemies.
The player needs at least 31 Power Stars to battle him to gain the Bowser Key from Bowser in the Fire Sea to go to the upper area of Princess Peach's Castle. In order to reach Wario, Luigi had to become transparent so he may jump into the Wario painting in the room with the Snowman's Land world and go through the cold area so that Luigi may battle him. (The cold area contains 8 red coins that can be collected to receive the course's Power Star.)
His attacks involve him ramming into Luigi or breaking ice after Luigi knocks him into the icy water. He must be knocked into the icy water three times so that Luigi may gain the Wario Key to rescue Wario.
Mario Kart DS
He appears in Mission Mode as the sixth boss in Mario Kart DS. He is also faster, harder to push, pushes harder, and the player (as Luigi) must push him off the stage three times by using Triple Mushrooms to get momentum to knock him into the water. When he is pushed off the stage, he returns to the middle trickier and stronger each time, but after the second time he jumps back to the middle if Luigi tries to push him near the edge of the stage, he has to either hit him from the side, while he is not looking, or when he is charging. Otherwise he will jump, causing Luigi to more than likely fall into the water, losing a balloon. After he is pushed off the third and final time, Luigi wins the mission.
- It's possible to fight Chief Chilly as Yoshi if you can glitch through the Mirror. Chief Chilly has his own unique dialogue for Yoshi as well. Yoshi can still beat Chief Chilly with Ground Pounds and Slide Kicks.
- Chief Chilly's facial expressions looks very similar to the Millennium Star.