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Check the floor you want to reach and see if you have met the requirements.

Room Level Prize Items Needed Chapters Cleared
10 3 Tippi Card 1 Shroom Shake Chapter 1
20 5 Thoreau Card 2 Shroom Shakes Chapter 2
30 8 Boomer Card 3 Shroom Shakes Chapter 3
40 10 Slim Card 1 Emergency Ration Chapter 4
50 12 Thudley Card 1 Emergency Ration Chapter 5
60 13 Carrie Card 2 Emergency Rations Chapter 6
70 15 Fleep Card 3 Emergency Rations Chapter 7
80 16 Cudge Card 4 Emergency Rations Chapter 7
90 18 Dottie Card 5 Emergency Rations Chapter 8
100 20 Dashell 5 Emergency Rations Chapter 8

If you have all that, if you have Luigi go to Flipside B2, use super jump and hit the blue switch.

If you don't have Luigi, go to Flipside Outskirts, go down the pipe to your left, Go down another pipe to your left, find the hidden blocks with Tippi, jump across the blocks and hit the switch.

Each room in the Pit of 100 Trials resembles the LCD display from Nintendo's old Game & Watch devices. It is highly recommended to stay in 2D mode for this reason because flipping to 3D reveals the 2D nature of the backdrop, causing you to fall to the floor.

In every room there are a few enemies. One random enemy has the key. Kill the enemies until one drops a key. When you get the key, unlock and go through the door. Remember, each room has a time limit, so work quickly. Every tenth room you get a card as well as the opportunity to bail out of the pit and try again from the beginning another time.

Room Enemies Tactics
1 Squiglet Jump
2 Goomba Jump
3 Squig, Squiglet Jump
4 Sproing-Oing Jump
5 Goomba, Gloomba Jump
6 Cherbil Jump
7 Sproing-Oing, Squig Jump
8 Squig, Squiglet Jump
9 Gloomba, Poison Cherbil Jump
10 Tippi Card Go through the door