Ring of Pain

Restart the first floor until you get Hermit's Tiara.

Then, you're aiming to:

Build up your speed, health, then attack.
Replace the spoon with something else. Ice Breaker (gray, can be found in first floor) is good with the Tiara.
Find Soul/Stone Scream books (blue item, so a random early Ambush room is always beneficial, if you have a good pile of souls).

From here, apply the common Tiara/Scream strategy whereby you freeze enemies, whittle them down (best to lower your attack after you get the book) and kill them with scream to level it up. Take on Owl as the boss and hit him with massive damage each cast with the scream book.

Since I didn't see any guides here I figured I'd add a few tips that helped me for this.

I found that the beginning of the run was the hardest part of it. Here is what I would do to get the run started:

- In the first room get Pain's Reward. Keep restarting and rerolling until you do. Sometimes it does take a bit but this was crucial for me to even get the runs going. Make sure to stay under 5 or less health before you exit a room, might need to take a hit or curse potion. Keep Pain's Reward for the first 5-6 main rooms and you should have enough health by that point (going through the side rooms also) to switch it out. I found that after room 5 or 6 its just too hard to balance out survivability.
- Wading Rags is also an extremely good item to find and keep.
- I basically focused everything on Attack but made sure my Defense didn't go negative before the final ending choice.
- I did this on the light ending.

Hope that helps!