Guide to hobo boss smackdowns (which I hope is readable; it started out nicely tabbed...)

(Revised Dec 6 with Jef's and Dawn's improvements) 

Use hobo summoning for itemdrop?  Either wear Hodgman's outfit or use a dinged-up triangle (combat item, 10 hobo nickels, consumed on use)

Path of the Roach for 50% itemdrop (Extra Sensory Perception). 

Path of the Mole for +10 lbs familiar weight (Bureaucratized)

Set Strung-Up Quartet to "Le Mie Cos Favorite" for 5% itemdrop

Scented massage oils

Gobs of wet hair to keep Zombo and Scratch stunned and unable to strip your buffs or equipment.

    Or Dawn suggests superamplifed boom boxen or macrame nets, which also delevel and do ~100 damage.

Divine combat items  (Blowout = Moxie; Silly string = Myst; Noisemaker = Muscle)

Colon Annihilation and Possessed Tomato for Frosty 

Familiar: hound dog has best +itemdrop, or disembodied hand plus stickersword with 3 unicorn stickers

Consumables listed here need:

  6 SPLEEN: prismatic wad, twinkly wad, glimmering raven feather, off-white oyster egg

  6 DRUNK: elven moonshine, orielle brandy

  2 FULL: honey-dew 

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* CHESTER: Can't use combat items.  Just pound him with attack or spells.

     Outfit: itemdrop with Hodgman's 

* OSCUS: Work quickly because of stench damage (no prob with Dogsgotnonoz & various protections.)

     Outfit: itemdrop with Hodgman's 

* FROSTY: Check that +ML is 0.  First funksling a colon annihilation and possessed tomato, then hit with prismatic damage.

     mechamech, infinite pencils, yohohoyo, plastic pumpkin bucket.  

     (with the two funkslung items you probably don't need all these. Also I'm not sure if yoho adds prismatic damage on top of the prismatic wad +damage)

     Outfit: itemdrop with hodgman's and yohohoyo and cup of infinite pencils

* ZOMBO: GET THE JUMP. Removes clothes, resists elemental. Funksling gobs of wet hair and divine items.

     Outfit: itemdrop  (you won't be able to summon a hobo underling)

* SCRATCH: GET THE JUMP. Debuffs you.  Funksling gobs and divine items. 

     Outfit: itemdrop  (you won't be able to summon a hobo underling)

*HODGMAN divine items (whack or spellsling if you're tuff enough) He has ~25,000 HP.

     Outfit: itemdrop with Hodgman's, though you'll probably need equipment to enhance your power.

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GET THE JUMP (I don't know how much init you need; all these are probably overkill)

panty raider Hiding in Plain Sight 100%

upsy daisy Ass Over Teakettle 50%

Arena White-boy Angst 50%

springy fusilli buff 40%

ant agonist All Fired Up 30%

swabbie swab Well-Swabbed Ear 30%

yellow heart Heart of Yellow 20%

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Miscellaneous (This list emphasizes maximizing Myst)

handful of hand chalk Chalky Hand don't fumble

astral shell buff protection

elemental saucesphere buff protection

Jabañero Saucesphere buff damage for Frosty

Jalapeño Saucesphere buff damage for Frosty

Scarysauce buff damage for Frosty

pool table Billiards Belligerence weapon damage 50%, +5 lbs

pool table Mental A-cue-ity spell damage 50%

pool table Hustlin' init 50%, item 10%

dogsgotnonoz Can't Smell Nothin' stench protection

can of black paint Red Door Syndrome so-so resist

prismatic wad (3 SPLEEN) Rainbow Bright attributes +30%. Serious resist. prism dmg.

elven moonshine (3 DRUNK) Drunk With Power spell damage +100%

funky dried mushroom Seeing Colors myst 50%

ointment of the occult Mystically Oiled myst 100%

Hawking's elixir On the Shoulders of Giants myst 200%

potion of temporary Gr8tness myst, mus, mox +100%

Ferrigno's elixir Incredibly Hulking mus 200%

twinkly wad (1 SPLEEN) Aspect of the Twinklefairy mys, mus, mox +10%

Other wads:  Mus Mys Mox

  hot        30  10  20%

  cold       30  20  10

  stench     20  30  10

  spooky     10  30  20

  sleaze     15  15  30

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FAMILIAR WEIGHT:

pet snacks Healthy Green Glow 10 lb 

Chorale of Companionship AT buff 10 lb

Path of the mole Bureaucratized 10 lb

Sugar shield? (pumpkin bucket is probably better) 10 lb

Empathy buff 5 lb

Leash buff 5 lb

black snowcone Black Tongue 5 lb

disintegrating spikey Man's Worst Enemy 5 lb

pet-buffing spray Heavy Petting 5 lb (also all attributes -10%)

green heart Heart of Green 3 lb

half-orchid Bestial Sympathy 3 lb

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ITEMDROP:

Summon hobo underling (ask him to dance) 100%

cyclops eyedrops One Very Clear Eye 100%

glimmering raven (1 SPLEEN) Melancholy Burden 60%

llama gong Extra Sensory Perception 50%

pressurized potion of percept Perceptive Pressure 50%

honey-dew (2 FULLNESS) Mmmmmelon 30% 

orielle brandy (3 DRUNK) Hoity Toity 30%

blue-frosted astral Cupcake of Choice 30%

black OR blue snowcone Black/Blue Tongue 30% (also 5 lb familiar weight with Black)

Friar Brother's blessing Smothers/Corsican Blessing 30% (food or booze only)

Thingfinder AT buff 20%

Phat Leon's AT buff 20%

knob goblin eyedrops Peeled Eyeballs 15%

lavender heart Heart of Lavender 10%

off-white egg (1 SPLEEN) Eggs-tra Sensory Perceptn 10%

Clan buff Bootyliciousness 10%

eyedrops ocelot Ocelot Eyes 10% 

eyedrops ermine Ermine Eyes 5%

DoD potion Object Detection 5%

Porquoise juice Je Ne Sais Porquoise 5%  Also Moxie +50%, Meat +6%

love song of disturbing(4) Withered Heart X%, x is remaining turns of effect up to 20