Re: WoTL 1.666

The easiest way I found to do the darkboy / mamas boy achievements was to select Challenge 7 "Meat 4 Evar!" combined with character switching to Cain.

You can character switch by clicking the challenge, then hit escape, space and right or left on the dpad to select a different character. Just make sure you do it before the screen fades to black.

Switching to Cain on challenge 7, means you start with a full meat boy AND the lucky foot. The meat boy is extremely useful for killing enemies without you having to be near them. The lucky foot will guarantee that all pills will give positive effects.

This strat is also less luck dependant than aiming for very select items.

Some other things I found useful were, heading straight towards the bosses on the earlier floors, to maximise chances of being able to do deals with the devil. I'd take most deals because health is not a priority.

Being able to locate the boss rooms are good so the crystal ball / map / compass/ Magic 8 ball/ The World/ The emperor/ The sun Tarot Cards are worth taking.

Flight is also good to have so Lord of the Pit/ Transcendence/ Pony/ Holy Grail/ Fate/ Spirit of the Night/ Dead Dove / Becoming Guppy.

Invulnerability items like My Little Unicorn / Book of Shadows / The Chariot tarot card are also good to have for getting out of tight spots. I also found the The Candle quite useful for quickly getting rid of some enemies that were too close.

Lastly skatole from the arcades which I aimed to get on every run, it just takes the hassle of the flies out the equation.

I tended to keep around 10 coins going between floors, to maximise chances of an arcade showing and having a bit of cash in case the shop has an item I'd like. I found the Fortune telling machines more useful than the slot machines for getting soul hearts, tarot cards and trinkets.

In the end the item that guaranteed my Dark Boy run was Spirit of the Night and the Book of Shadows.

An easy kill on mum using the Bible is probably possible, but I never encountered it in any of my runs.

Edit 1: So, I've had some questions and further thoughts that I will briefly summarise. Try and maximise all power ups and stat increases throughout the basement and caves. Trade as much hearts as you can. You just want to avoid taking ANY damage in the Depths I & II OR The Womb I & II. You should aim to use A Forget Me Not within the first four floors, AFTER you have beaten the boss and taken every single item of use.

I want to stress that finding the boss room on floors 5 & 6 and/ or 7 & 8 is very important. You want to be in as little rooms as possible to avoid unnecessary risk. Take the shortest route, straight to mom. If I picked up an Emperor card I'd save it to use on the second floor. I.e. beat the boss on the 5th floor, go down to floor 6th and instantly use it to go straight to the mom fight.

If you get hit say on the depths, then keep playing on, I actually got mamas boy before dark boy!

Lastly, make sure you aren't playing on eternal mode!

Let me know if the guide has helped you :)