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the counter should say 999 or 999 coins in playthroughs ?
HP+, any damage related activateables, or any use items that might not be good and you should think of holding R. Take a run as far as Caves 2 to see if you want to go past that or hold R once more to save time. Also take the time to look for everyone secrect room possible. Don't bother with super secret rooms though as they wont help the Lost but for a pill room and if RNG is kind that run.
The lost is a PAIN and there is no way to get around it. And I suggest that you don't cheat. Ruins the feeling of winning a run when you do and trust me when I say that nothing is better than pulling a win by the skin of your teeth.
Keep an eye out for the OP combos. Gnawed Leaf + Lil Haunt/Ball of Bandages/etc. guarentees a win, so long as nothing in the room attacks you in less than a second. Guppy form + a constant attack like tech2/brimstone = gg. Pyromaniac + kamikaze literally makes you invincible, so long as you spam that kamikaze, and even without kamikaze you're immune to mom/satan stomp attacks.
Some people like Mom's Knife, but personally I'd avoid it. It's easy to get reckless with it and its range puts you in a deceptive amount of danger.
Don't be afraid to reset a dead cat. Sometimes the items just aren't on your side.
NON-RAMBLING THOUGHTS START HERE.
PLAY. ON. HARD MODE. With The Lost, it honestly doesn't make that much difference EXCEPT that it's required for one of his unlockables. If you don't play on hard mode, you will regret it when you come back for extra runs.
Fact: As The Lost moreso than any other character, THE SHOP IS YOUR BEST FRIEND. Some of his very best items (Stopwatch/Humbling Bundle/Candles/etc) are found in there. Stock your donation machine and abuse it. Also helps when you need a clutch bomb/key. If you have at least 7 coins (or bombs and a well-stocked donation machine), go out of your way to check the shop, even if you only have one key and haven't opened treasure room.
Personally I like floor one Labyrinth curse, but here's some things to consider for your own runs:
First floor Labyrinth pros:
Two free treasure rooms
Immediate devil room
First floor labyrinth cons:
Only one shop (see above fact)
Can be more taxing on the player (I.E. extremely large and linear, with everything useful on the other end of the map)
Curse Rooms: These are the biggest gambles with The Lost. Personally I never take them past first floor unless I KNOW I can get out, but it's your choice. Here's some exit options:
Teleport-based cards (The Moon, The Stars, The Fool, The Emperor, etc.)
Holy Mantle
Invincibility-based activatables (My Little Unicorn/etc.)
Bombing in through a secret room.
Curse room pros: Potential for extremely powerful items for The Lost (Goat Head, Dead Cat/Guppyform)
Curse room cons: CAN GUARANTEE A DEATH.
ITEMS
Godtier passive found items:
Dead Cat (if you get something else that's at least decent)
Holy Mantle (Do I really need to explain this?)
Pyromaniac (Early if you get good explosive stuff, late because mom/satan stomp immunity. Also immortality combo.)
Goat Head (Moar satan rooms!)
Gnawed Leaf (Gamewinning combos. Watch out for rooms where you're attack in under a second!)
Ludovico Technique (if you're good with it OR have/plan to have brimstone/tech2).
Dollar (Unlikely to happen, but when it does, the shop is yours.)
Godtier activatable items:
The Pinking Shears (At first I wasn't a fan. Then I found out how quickly it tears bosses apart).
Red/Blue Candle (Deceptively high damage, and reusable, so don't need to save for boss room! And don't worry: The flames don't hurt you.)
Kamikaze (Only with pyromaniac. If you have both, constantly activate it to be unkillable.)
My Little Unicorn (Good boss killer. Also lets you survive a clutch situation.)
Unicorn Stump (If you have an orbiting damager, this is an improved My Little Unicorn.)
Tammy's head (Absolutely brutal with the right combo's. Just don't get killed by a stray shot if the enemies shoot right away.)
The Bible (Conditional: If you're not confident in fighting Mom/Mom's Heart/It Lives. Other activatables are recommended if you are or already fought them that run.)
Godtier shop items:
Stopwatch (I cannot stress this enough: If you plan on playing The Lost, unlock it. It's ALWAYS worth the 15/7 coins.)
Red/Blue Candle (See above)
Humbleing Bundle (You'll never be short on bombs/keys again. Also moar money for shops!)
The Bible (See above)
There's Options (Because the choice between A Snack and Torn Photo is a good choice to have, as opposed to being stuck with A Snack.)
Other good items (I.E "It's not a guarenteed run, but I'm willing to see how it goes for a floor or two" items):
Cricket's body (Splash around corners)
20/20 (essentially doubled damage, combos extremely well with Cricket's body)
Death's Touch (Piercing, boosted damage, AND scythes have a larger damagebox than tears.)
PHD/Virgo (No more "bad" pills, but watch out for explosive diarrhea still.)
Skatole (flies begone!)
Brimstone (The chargeup time is the only reason this isn't in godtier. If you get combos, it becomes godtier.)
The Mulligan (Lesser guppyform, still brutal.)
Libra (6 of each item, and combos extremely well with polyphemus/soy milk/other extreme stat changers. Also activates if you get it BEFORE said stat changers.)
Mom's Wig (Spider Mulligan. Brutal with tech2/brimstone/hive mind)
X-Ray Vision (Secret/Super Secret for free every floor? Sure!)
Spoon Bender (Godtier with brimstone/tech2)
Cricket's head (Not amazing, but notable as one of the larger damage ups.)
Most familiars (More damage is good. Notable are Mongo Baby and lil' Brimstone.)
Good Trinkets:
Cancer (This was arguably the best trinket in Isaac 1. It's still brutal here.)
Paper Clip (Free chests? Yes please!)
Whip Worm (For when you need just a bit more range.)
AAA Battery (moar item usage)
Flat/Burnt/Counterfeit Penny (Anyone who's used these know how good they can be with a little luck.)
Lucky Rock (Every rock destroyed gives you a penny. Trust me: This can add up fast.)
Store Credit (Self-explanatory)
Broken Remote (conditional: Use it to check curse rooms and have a guarenteed escape. Otherwise it can come back to bite you. If you have a choice between this and another trinket when going to the next floor, take the other one.)
Godtier combos:
Pyromaniac and Kamikaze (keep pressing space and you're immortal.)
Pyromaniac and most other explosive weapons (no more fear of self-damage)
Guppyform/Mulligan/Mom's wig [to a lesser degree] and brimstone/tech2 (Endless flies)
Gnawed Leaf and Lil' Haunt/Gemini/Etc. (immortal while able to attack.)
Brimstone/Tech2 and Spoon Bender/Ludovico Technique [both preferred] (You have to see it to understand. It's brutal though.)
Brimstone and Inner Eye/Mutant Spider (Slow RoF, but more beams = MASSIVE damage boost. Try to clear the room in one shot, or have a safe spot.)
Cricket's Body, 20/20, and tear RoF boosters (Pretty much unavoidable tears. Add in The Parasite for even more splash!)
One last tip, and this is perhaps the most important: DO NOT PLAY WHILE TIRED. I once threw away a holy mantle/guppyform/brimstone run because I fell asleep for 10 seconds. I nearly threw my laptop out the window. If you're playing and you get a good run, MAKE SURE YOU ARE ALERT. If you're not, go to sleep and finish later.
And don't be a noob, don't use the alt-f4 reset when you die, it's so lame and sadly most of the real platinum gods got it by that exploit and now they brag about it in the "club". The lost is very hard but doable.
Id move Moms Wig up a bit. It doesn't need you to hit mobs to spawn spiders. Just hold the fire key and you have a spawn chance every time you fire or a tick of charge, even in empty rooms. So higher ROF = faster spiders. This lets you spack up to 5 spiders from the wig to enter every room with. That is 2.5 * 5 your current damage to nuke any mobs that comes close to that door making it much safer against melee mobs.
With Hive mind the spiders double in damage (*5) and you can now spawn up to 10 from the wig. And no, any spiders you already had to gain from other means do NOT count to the Wig spawn cap much like the infested baby and its one fly.
Moms Wig is what mainly got me the boss rush kill thanks to the spiders always being about the room doing massive damage to bosses with letting me focus on dodging instead of doing constaint damage.
1. Dead cat, this item granting you 9 lives is the only thing I wish for when entering a devil room, the biggest troll is getting angel room wafer runs.
2. Holy mantel, the only reason I would want angel rooms in a lost run.
3. The Soul, this item is unlocked by playing as the lost anyway but if you are lucky enough you can find it in your item room or angel room and you are pretty well off at that point, but not invincible.
4. The Gnawed Leaf and any item that will do its own damage such as the leech, daddy long legs etc, you'll win, slowly.
5. orbitals, wether it's 3 flies or meat boys, angels and daggers this is very important when it comes to playing as the lost.
6. Damage, if you end up in a lost run without the rest of this you may as well restart, I have had some lucky no damage runs without protection but I couldn't beat blue baby with it, you'll lose unless you're strong or protected.
7. If all else fails, use the cheat engine but don't tell anyone, you get looked down upon for that, although I never used a cheat engine for the lost, I thought about it a lot.
Hope this helps, it's mostly just top of my head stuff but this is what got me through that evil character, it was a pain but it definitely keeps you on your toes and shows you where your stress levels are.