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Chief Chilly is a boss who appears in Super Mario 64 DS and Mario Kart DS. Resembling a larger version of the Chill Bully, he is much larger than an average Bully and has a spiked mustache and a crown of ice crystals.
Super Mario 64 DS
Before the events of Super Mario 64 DS, Chief Chilly locked Wario up and was told by Bowser to guard the key to Wario's door. Chief Chilly is found at the end of the stage Chief Chilly Challenge, which only Luigi can access using a Power Flower in the room with the large mirror. Once the player enters Chief Chilly's arena, he states that he locked Wario up because he was rude and mocking Chief Chilly's mustache.
Within battle, Chief Chilly acts like a Big Bully; he can be attacked only by punching or kicking him off the stage. Every time the player manages to do so, Chief Chilly makes the stage smaller and then hops to the middle of the stage. If the player is standing in the middle of the stage, they take damage. On the third attempt of pushing Chief Chilly off the ledge, he manages to stay on the ledge while off-balance, so the player must hit him once more to deal the final blow. Failure to do so results in Chief Chilly regaining his balance. Once Chief Chilly has fallen for the third time, he grants the player Wario's key.
Mario Kart DS
In Mario Kart DS, Luigi must battle Chief Chilly on Level 6 of Mission Mode. Like in the battle with the Big Bully, Luigi must push Chief Chilly off his platform into the water. However, Chief Chilly must be pushed off three times instead of one time and becomes stronger and trickier with every successful attack on Luigi's part. However, after he falls into the water for the second time, he gains the ability to jump over Luigi's boost attacks. To defeat him, Luigi has to approach Chief Chilly, then attack him either from the side, where the boss is unable to see him, or while the boss is charging at him, which knocks both of them backward. Luigi can attack him either from afar or in close proximity to him.
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