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 the other bosses of Super Mario 64 DS, Chief Chilly takes great pride in his moustache.
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 Chllly will be able to jump over Luigi's boost attacks. To defeat him, Luigi had to attack Chief Chily from the side, where the boss couldn't see him.