Chief Chilly resembles a crystallized version of a Big Bully. He is a large ice Bully and is apparently the leader of all the Bullies. He first appears in Super Mario 64 DS, the Nintendo DS remake of Super Mario 64. Bowser hires him, along with his other minions, to trap the three heroes of the game. He is much larger than an average Bully and has a spiked mustache and a crown of ice crystals. Out of all the mustached bosses in the game, Chief Chilly takes pride about his mustache. He later re-appears as a boss in Mario Kart DS.
Super Mario 64 DS
In 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 mustache. 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 him the key to Wario's prison. Chief Chilly disappears after the battle to restyle his mustache and to vow revenge.
When first encountered, Luigi must try punching him into the ice cold water. Then, he tries to strike back by ramming Luigi into the ice cold water back. When Luigi falls into the cold water, he loses health. When Chief Chilly falls into the ice cold water, he comes back out and breaks edges of the ice platform the two of them are on. Luigi must then repeat this step two more times, making three total to fully defeat Chief Chilly and gain the Wario Key. It is best for Luigi to smash him while he is 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, Chief Chilly is the sixth boss in the Missions option and Luigi battles him, much like he did in Super Mario 64 DS.
Like last time, he tries to ram Luigi in the water and even one fall in there makes Luigi fail the mission. Like the battle with Big Bully or Bully, Luigi must attack him with using a Mushroom or Triple Mushrooms. When he falls off of the arena twice, Chief Chilly renders a new tactic by making him capable of jumping over Luigi. Luigi must continue avoiding his attacks and ram into him again to fully defeat him and win the mission. Chief Chilly is faster, stronger, and slightly more intelligent in this game.
- To Yoshi: "Hmm? I see you have no mustache. Poor, bald, little creature. It's not a fair fight for you, but luckily, I'm not a fair fighter. Let's go!"
- (defeated) "I simply cannot believe that I lost to a hairless pip-squeak like you! My mustache was my only joy. Now what am I going to do?"
- To Mario: "You there with the mustache! I am the king of cold, Chief Chilly. I lock up anyone who challenges the greatness of my mustache. I am the mustache master! In fact, I locked up a rude fellow just the other day. Hmph!! The nerve of him, coming to my realm looking like that. Your mustache is not altogether bad. Not as grand as mine, of course. But what insolence in trying to show me up! I shall shave that fuzz right off your face. Here I come!"
- (defeated) "Dang!! There's someone with a greater mustache than mine? Ridiculous! Does that mean you're cooler than me too? You might be gifted follically, but you better watch out once I get my mustache styled."
- To Luigi: "You there with the mustache! I am the king of cold, Chief Chilly. I lock up anyone who challenges the superiority of my 'stache. In fact, I locked up one such fellow the other day. Hmm. What a sad, mangy mustache you've got there. It hardly seems worth it to destroy you. With a 'stache like that, you're clearly the sidekick, not the star. But I'm in 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!"
- defeated) "No way! I lost to such a scrawny guy like that...? Hmmmm, did I not groom my mustache well enough? I must hurry home and condition it...Farewell!"
- To Wario: "You there with the mustache! I am the king of cold, Chief Chilly. I imprison those who challenges the greatness of my mustache. In fact, I locked up a man up just the other...What's this? You look just like the impertinent mustached man I locked up the other day. Has everyone been taking mustache grower? There's only one way to settle this once and for all. We'll battle man-to-man to see who has the best mustache! Let's rumble!"
- (defeated) "Oh noooooo! I lost! Augh! My mustache...My pride and joy, my reason for living! Now I suppose I'll have to explore new pursuits."
- Big Bully - Super Mario 64
- Chill Bully - Super Mario 64
- Bully - Super Mario 64
- Baron Brrr - Super Mario Galaxy
- By using Action Replay or a glitch to go through the mirror with Yoshi, text for Yoshi is revealed when battling Chief Chilly (possibly beta text). Although Yoshi cannot punch or perform most kicks, ground-pounds, crouching, sliding kicks, or sweep kicks still work against him). Chief Chilly has special quotes for when facing Yoshi and when being defeated by him.
- Chief Chilly's facial expressions looks very similar to the Millennium Star.
- Additionally, his facial expressions greatly resemble Waluigi's.