Cool, Cool Mountain

Cool, Cool Mountain is the fourth World found inside a painting, in the games Super Mario 64 and Super Mario 64 DS. The entrance is on the first floor of Princess Peach's Castle, and behind the other star door labeled "3". It is the home of several Penguins and Spindrifts. There are three cannons, a Slide, and a teleportation area at the end of the broken bridges. Bottomless pits surround this mountain, as it appears to be floating in the sky, so it is possible to fall off the course.

Mario starts out at the summit (unlike Tall, Tall Mountain) and must progress down the icy slopes all around the mountain. At the summit is a house with an oversized chimney that Mario can enter. Inside is a large penguin that will race Mario on a huge ice slide. In between the top and bottom is the Headless Snowman.

Levels
The level titles and numbers correspond to Super Mario 64 unless otherwise noted.

Star 1: Slip Slidin' Away
This level is the same in both Super Mario 64 and its remake, Super Mario 64 DS. Appearing on the summit of the mountain, Mario starts off the level near a small house with a massive chimney. Mario should jump into the chimney and will be transported into the house revealing a slide inside of it. Sliding down and avoiding falling off the slide, Mario will soon come to the end of it and land inside what appears to be another room of the house. Opening the door will take him outside and a Power Star will emerge.

Star 2: Li'l Penguin Lost
Sliding down to the bottom of the mountain, the player should see a penguin in a small pool of water. Talking to it, Mario will find out that she has lost her daughter. Returning to the summit of the mountain, Mario will see a small penguin that was there upon entering the level. Realizing that it is the missing penguin, Mario picks her up and returns her to her mother. The adult penguin then rewards him with the second Power Star.

This level is the same in Super Mario 64 DS, except for the fact that Mario, Luigi, and Wario can be played as. Yoshi can only beat the level if he uses a cap, as he will spit out the penguin immediately after eating it.

There's another penguin on top of the house. If Mario gives it to the mother, she says it's not hers.

Star 3: Big Penguin Race
This level is the same in both Super Mario 64 and its remake. Returning to the house, Mario will find a large Penguin standing in the front of the slide. Once Mario approaches him, he will challenge the plumber to a race (much like Koopa the Quick), to see who reach the bottom first. If Mario is able to beat the penguin, it will reward him with a Power Star. However, if Mario takes the hidden shortcut while sliding down or if he skips part of the slide by jumping to a lower part, he will be accused of cheating, and the penguin will not give up the star.

Star 4: Frosty Slide For 8 Red Coins
Looking around, Mario will see Red Coins located in places all over the mountain in the Super Mario 64 version. The first one is located on the tree near the house. Another one is located at the bottom of the slide. One is located at the top of the rope swing, one is on the cliff in the middle of the mountain. There is a coin on a tree at the bottom and another one by the warp under the mountain. The last one is by the severed bridge after the bridge with the hopping snowmen. The other side of the bridge holds the Star Marker were the star will appear once the last coin is collected.

This mission was changed in the Super Mario 64 DS version. The change was that to obtain this star the player must need Yoshi, because at the beginning on the summit the first red coin is in a ice cube. Yoshi is able to eat the fire beside the snowman's head, and blow it out to melt the ice. Yoshi must to the same thing with the one that's cliff in the middle of the mountain, the others are exactly the same way as the other version.

Star 5: Snowman's Lost His Head
This level is the same in both Super Mario 64 and its remake. For Mario to acquire this Power Star, Mario should head to the left of where Tuxie is found and see a platform with a snowball on it. Upon approaching it, it will tell Mario that it is looking for a new head. Hearing that Mario knows a certain head looking for a body, it starts rolling down the slopes of the mountain, growing in size as it accumulates snow. For it to find the Snowman's head, Mario must get in front of the snow ball and direct it to its new home. If Mario does not lead it, or slides ahead the snowball and takes a shortcut into Snowman's head face, it will aimlessly miss its destination and fall off the course (or even into the cannon). Succeeding in giving the Snowman a new body, the grateful Snowman will reward Mario with his next Star.

Star 6: Wall Kicks Will Work
To obtain this star, Mario must make use of the cannon in this level, found at the base of the mountain near the exit cabin for the big slide, unless he uses a Spindrift and floats down that way. Like all cannons in the game, Mario must first speak to a Bob-omb Buddy to be able to use it. The Buddy is located on a small floating island along the path of the wooden lift that is just to the left of the cannon. With the cannon, Mario must shoot himself to the tree on the other side of the level (as not to overshoot and fall). Then he must make his way along a sheer cliff face with a couple of Spindrifts, and long jump across a pit. On the other side, Mario must run up the first slope and wall kick to another sloped platform. Now running the other way up this platform, the player should triple jump and wall kick at the apex of the jump. (If the triple jump is botched, there is a spinning heart in plain sight that can be used to recover health). Once on the last platform, Mario will need to be careful to cross the narrow ice bridge here and claim the Power Star.

In Super Mario 64 DS, the name of the mission was changed to Mario's Super Wall Kick, since Mario is the only one who has that ability out of all the playable characters. However, Luigi is capable of reaching the star by backflipping to the higher platform, using his special twirl. Other than that, the level is the same between the two games.

Star 7 (DS): Switch Star Of Cool, Cool Mountain
In Super Mario 64 DS, there is an added star that Wario must collect in Cool, Cool Mountain. The Star Switch is on the small floating isle where the Bob-omb Buddy is, and then the Power Star will appear bellow the small ice beside the mother penguin is. Wario can ground pound the ice and obtain the Power Star.

Trivia

 * After Mario has 120 Power Stars, he can go and race the penguin again, except he has become massive and more difficult to beat. There is no reward for winning the race again, except for praise from the penguin.
 * A quick reference to Santa Claus, who has a more major role in other forms of Mario media (such as cartoons), is made on a sign near the starting point of Cool, Cool Mountain.
 * Oddly enough, in the Super Mario 64 DS version, it is possible to get 255 coins (the maximum number of coins allowed) by entering the cabin again and again and defeating the Goombas with caps and/or destroying the bricks (next to the bodiless snowman). This is also true in Snowman's Land, by entering and exiting the igloo.
 * The music that appears here (as well as the music for Snowman's Land) is actually a remix of the music of The Princess's Secret Slide and Rainbow Ride.
 * In the original Super Mario 64, the pool around the mother penguin is liquid water. However, in the DS version, the pool is frozen to facilitate the new Switch Star.