This achievement was a joke once I watched this speedrun video:
It involves basically breaking the entire game using a couple of clipping glitches that are mindbogglingly easy to perform.
No only that but you can skip the entire trading sequence, at least 3/4s of each dungeon and at least 2 bosses.
The real challenge will be the last boss, but after trying for at least 20 tries you will remember everything she does and can kill her without any damage done to you and without using items, like I did.
1. "Pit Clip": Whenever you fall into a pit or water press
and then press
on your "Jake Shield" then return to the game and you are now in "Clipping mode" which allows you to pass through walls.
2. "Big Box Clip": Once the Hero's Gauntlet is acquired you can move big boxes, if you move a big box so that 1 side is touching half a wall or object you can "grab" with
the side that is halfway and clip into the object and any wall.
3. "Jake's Ring Clip": Once you have Jake's Ring you can summon Jake as a playable character but if you summon him almost directly onto a wall Jake will clip into it allowing you to move Jake onto walls.