Flipside Pit of 100 Trials

The Flipside Pit of 100 Trials is a one hundred-room labyrinth in Super Paper Mario, just like in Paper Mario: The Thousand-Year Door. However, in this game, there are two pits – one in Flipside and one in Flopside, the latter of which is called the Flopside Pit of 100 Trials. Both were created to test the forces that guard the Pure Hearts. The Flipside version was created to study the powers of the Pure Hearts. The switch that opens the Flipside version is located above the entrance. After gaining Boomer, one can simply go to the lowest level on the outskirts of Flipside. If they look around with Tippi, one can reveal a route to a bunch of blocks. Mario can then flip on the blocks and a secret passage will appear, which will lead to the ledge with the blue block to open the way to the Pit. This is hinted at by Garson. Alternatively, Luigi can super jump up to hit the switch.

In the Pit, a random enemy in each room holds a key to a locked door that proceeds to the next room. Every tenth room, a valuable item awaits. Wracktail is the boss waiting at the end of the pit. These pits are designed to look like the LCD screen of an old Game & Watch system.

Both pits have artwork on the walls depicting a Pure Heart and where it is found, which changes every 25 rooms. For example, Rooms 1-25 have a Pure Heart paired with Flipside and Flopside (a reference to Mario's first Pure Heart), while Rooms 51-75 have Merlee and her mansion, with the corresponding Pure Heart. Also, Rooms 76-99 show Fort Francis, with the Pure Heart inside. Room 100 seems to be designed to simulate the area in which Fracktail is fought and even has the same music from the Yold Desert and a circular patterned floor which can be seen to act like sand when Wracktail rises from the ground.

The walls of the pit are covered with faint images of doors, which each represent the possible location of any door in the pit. This is accurate for the visual LCD style of the pit, as many devices with this type of screen rely on faint  background shapes being filled to appear as images. The rooms in the Pit switch around every time the Pit is entered. This indicates there may be more than 100 rooms in the Pit, although the player only needs to go through 100 rooms to reach Wracktail. The enemies in the Pit always start off easy in the earlier floors, then gradually get stronger. The list below is accurate in describing the positions of enemies.

Room 1-9

 * Squiglet (Rooms 1, 3, 8)
 * Goomba (Rooms 2 and 5)
 * Squig (Rooms 3, 7 and 8)
 * Sproing-oing (Rooms 4 and 7)
 * Gloomba (Rooms 5 and 9)
 * Cherbil (Room 6)
 * Poison Cherbil (Room 9)

Room 11-19

 * Koopa Paratroopa (Room 11)
 * Koopa Troopa (Rooms 11, 14, 16 and 19)
 * Paragoomba (Room 12)
 * Spiked Goomba (Room 12)
 * Shlurp (Rooms 13 and 15)
 * Bald Cleft (Room 13)
 * Flip Goomba (Room 14)
 * Boomboxer (Room 15)
 * Tileoid G (Room 16)
 * Flip Koopa Troopa (Room 17)
 * Buzzy Beetle (Room 18)
 * Squig (Room 18)
 * Koopatrol (Room 19)
 * Squiglet (Room 19)

Room 21-29

 * Spiny (Room 21)
 * Boo (Room 22)
 * Gloomba (Room 22)
 * Fuzzy (Room 23)
 * Cherbil (Room 23)
 * Boing-Oing (Room 24)
 * Sproing-Oing (Room 24)
 * Chain Chomp (Room 25)
 * Crazee Dayzee (Room 26)
 * Paragoomba (Room 26)
 * Squiglet (Room 27)
 * Hammer Bro. (Room 28)
 * Koopa Troopa (Room 28)
 * Rawbus (Room 29)

Room 31-39

 * Tileoid B (Room 31)
 * Tileoid G (Room 31 and 39)
 * Longator (Room 32)
 * Growmeba (Room 33)
 * Cursya (Room 33)
 * Squig (Room 33, 35 and 37)
 * Stone Buzzy (Room 34)
 * Bald Cleft (Room 34)
 * Choppa (Room 35)
 * Ninjoe (Room 36)
 * Spike Top (Room 37)
 * Buzzy Beetle (Room 37)
 * Magikoopa (Room 38)
 * Spiked Goomba (Room 38)
 * Fire Bro (Room 39)

Room 41-49

 * Clubba (Room 41 and 48)
 * Squiglet (Room 41)
 * Pokey (Room 42)
 * Gloomba (Room 42)
 * Koopa Striker (Room 43)
 * Squog (Room 44 and 49)
 * Squig (Room 44)
 * Cursya (Room 44)
 * Tileoid R (Room 45)
 * Tileoid B (Room 45)
 * Flip Paratroopa (Room 46)
 * Flip Goomba (Room 46)
 * Ice Cherbil (Room 47)
 * Poison Cherbil (Room 47)
 * Cherbil (Room 47)
 * Magikoopa (Room 48)

Room 51-59

 * Flip Spiny (Room 51)
 * Spiny (Room 51)
 * Buzzy Beetle (Room 51)
 * Pigarithm (Room 52)
 * Spania (Room 53)
 * Tileoid B (Room 53)
 * Dry Bones (Room 54)
 * Clubba (Room 54)
 * Hooligon (Room 55)
 * Dark Boo (Room 56)
 * Tech Cursya (Room 56)
 * Zoing-Oing (Room 57)
 * Ice Cherbil (Room 57)
 * Amazy Dayzee (Room 58)
 * Crazee Dayzee (Room 58)
 * Yellow Magiblot (Room 59)
 * Squig (Room 59)

Room 61-69

 * Beepboxer (Room 61)
 * Heavy Cursya (Room 61)
 * Cursya (Room 61)
 * Dull Bones (Room 62)
 * Dark Boo (Room 62)
 * Boomerang Bro (Room 63)
 * Clubba (Room 63)
 * Tileoid Y (Room 64)
 * Tileoid R (Room 64)
 * Blomeba (Room 65)
 * Growmeba (Room 65)
 * Skellobit (Room 66)
 * Ninjoe (Room 66)
 * Longadile (Room 67)
 * Longator (Room 67)
 * Flip Hammer Bro (Room 68)
 * Squog (Room 68)
 * Squoinker (Room 68)
 * Soopa Striker (Room 69)

Room 71-79

 * Moon Cleft (Room 71)
 * Bald Cleft (Room 71)
 * Jawbus (Room 72)
 * Cursya (Room 73)
 * Reversya Cursya (Room 73)
 * Tech Cursya (Room 73)
 * Heavy Cursya (Room 73)
 * Copta (Room 74)
 * Ruff Puff (Room 75)
 * Blastboxer (Room 76)
 * Beepboxer (Room 76)
 * Boomboxer (Room 76)
 * Blue Magiblot (Room 77)
 * Squog (Room 77)
 * Chromeba (Room 78)
 * Blomeba (Room 78)
 * Flip Skellobit (Room 79)
 * Flip Spiky Skellobit (Room 79)

Room 81-89

 * Hogarithm (Room 81)
 * Tileoid Y (Room 81)
 * Red Magiblot (Room 82)
 * Squoinker (Room 82)
 * Pink Fuzzy (Room 83)
 * Cherbil (Room 83)
 * Shlorp (Room 84)
 * Spania (Room 84)
 * Poison Pokey (Room 85)
 * Dark Boo (Room 85)
 * Koopatrol (Room 86)
 * Magikoopa (Room 86)
 * Chromeba (Room 87)
 * Reversya Cursya (Room 87)
 * Copta (Room 87)
 * Ninjoe (Room 88)
 * Ninjohn (Room 88)
 * Headbonk Goomba (Room 89)

Room 91-99

 * Gawbus (Room 91)
 * Ninjerry (Room 92 and 93)
 * Ninjohn (Room 92)
 * Ninjoe (Room 92)
 * Skellobit (Room 93 and 95)
 * Cursya (Room 93)
 * Flip Fire Bro (Room 94 and 96)
 * Squoinker (Room 94)
 * Spiky Skellobit (Room 95)
 * Flip Boomerang Bro (Room 96)
 * Squiglet (Room 97)
 * Red Chomp (Room 98)
 * Blue Magiblot (Room 99)
 * Red Magiblot (Room 99)
 * Yellow Magiblot (Room 99)

Room 100

 * Wracktail
 * Wrackle

Prizes in the Pit of 100 Trials

 * Room 10: Tippi Card
 * Room 20: Thoreau Card
 * Room 30: Boomer Card
 * Room 40: Slim Card
 * Room 50: Thudley Card
 * Room 60: Carrie Card
 * Room 70: Fleep Card
 * Room 80: Cudge Card
 * Room 90: Dottie Card
 * Room 100: Dashell (after defeating Wracktail)

The Flipside Pit Glitch
The pit is intended to be inaccessible (except by way of Flipside Outskirts) until the player has Luigi, but there is a glitch that can grant the player access before having him. The glitch involves setting Boomer on the ground, and switching to Thoreau. If the player times it right, Boomer will stay visible until he explodes. The player must then have Thoreau pick Boomer up and put him on top of the high ledge. If he is thrown as far back as possible, he will blow up the switch.

Trivia
🇵🇲
 * If the player beats the Flipside Pit of 100 Trials before going to Flopside, Wracktail mentions there being a Flopside Pit of 100 Trials. This is a hint that Flopside is an area in the game.