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The Pit of 100 Trials is completely optional, but it can get you some nice badges along the way. Although, there are no save points, no health blocks, and no comfortable beds. At the 100th floor, you will face the hardest boss in the game. I recommend getting the Strange Sack from level 50 and leaving immediately. Now that you have it, equip some Ultra Shrooms, Life Shrooms, Jammin’ Jellys, etc. Defense Plus, Spike Shield, Damage Dodge, Feeling Fine, Pretty Lucky, Feeling Fine P, and Pretty Lucky P are some of the recommended badges (that’s not to say that you need ALL of these). I also recommend entering when at least close to level 30 (around level 28). When you're ready go into the sewers.
Save in the thousand-year door room and go into the room to the right (use the airplane panel above the right spring). Enter the pipe in the center (BTW, First Attack and Bump Attack don’t work here so you might as well unequip them.
Pit of 100 Trials:
Enemies:
In every room (except 10, 20, 30, 40, 50, 60, 70, 80, and 90) you will have to fight 1 enemy before moving on. In every 10 levels (except level 100) there will be a big chest. Open it for a badge. At level 50, you will find the strange sack, which lets you carry up to 20 items. Here are the items:
Often along your travels, you will find movers and merchants. There are never any enemies where these guys are (they are also found in item rooms). Merchants sell items to you (they increase in price the farther down you go). Movers can take you down a few levels, for a price. If you’re not yet at level 30, don't bother using them since you will level up along the way. The last 10 levels can be considered as harder than the boss itself. The hardest enemies in the game are found here. Once you get down to the very bottom level, you will face the oldest brother of a certain two siblings.
Bonetail:
Goombella’s Tattle: That’s Bonetail. He’s the older brother of Hooktail. ...So old he’s just bones, in fact. Now THAT’S old. He has various breaths that might confuse us or put us to sleep. When his HP gets low, he’ll recover...or reanimate, as the case may be. He’s probably stronger than the last boss, seriously! Let’s do this right!
Quickly switch to your best partner (or one that has a lot of HP) and use Power Lift. Do as much as you can to make his HP disappear. When it runs out use Stylish moves to bring it back up quickly. Use any healing items when your HP is low. He will regain 20 HP when his HP goes below 100 and will continue to heal himself every several turns. Continue to focus on beating him and also keeping your HP above 15. After a while he’ll fall. And you’ll have beaten the strongest enemy in the game!
Bonetial will fall and spit out a big treasure chest. Get the Return Postage from it and celebrate your victory. Afterwards, leave this place and get back to home. Make sure to save your game after healing. Now you can get any badge, tattle or recipe you’re missing if you wish to.