Chief Chilly is a large Big Bully made of ice. He first appears in Super Mario 64 DS, the Nintendo DS remake of Super Mario 64. Out of all the mustached bosses in the game, Chief Chilly takes great pride about his mustache. Bowser hires him, along with his other minions, to trap the heroes of the game. He is much larger than an average Bully and has a spiked mustache and a crown of ice crystals.
Super Mario 64 DS
Before Lakitu informs Yoshi of the events transpiring in Princess Peach's Castle, Chief Chilly, along with Bowser, Goomboss, and King Boo, ambush Mario, Luigi, and Wario, the latter being put under Chief Chilly's protection. However, when speaking to a challenger, he claims that he locked Wario up simply because the brute challenged the superiority of his 'stache. Luigi comes to Wario's rescue and is forced to battle the monstrosity. Despite being the weakest of the three mustached heroes, he manages to beat the boss and push Chief Chilly off of his iceberg three times, giving Luigi the key to Wario's prison. Chief Chilly disappears after the battle to restyle his mustache and to vow revenge. During his first battle, it gets tricky, as every time he is pushed in the water, he knocks off portions upon returning, making it smaller. After taking a second hit, he rocks the iceberg and, when pushed to the edge, maintains his balance for a little before going back to the middle. It is best for Luigi to smash him while he was slipping, In other cases, Mario could also defeat Chief Chilly if the player picks up a Mario cap in the level.
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 time and becomes stronger and trickier with every successful attack on Luigi's part. However, after he falls for the second time, he gains the ability to jump over Luigi's boost attacks. To defeat him, Luigi has to attack Chief Chilly either from the side, where the boss is unable see him, or while the Bully boss is charging at him, which knocks both of them backward. Luigi can either attack from afar or in close proximity to his frozen foe. Chief Chilly is faster, stronger, and slightly more intelligent than Big Bully in this game.
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