New Monster – Smilin’ Jack

29 October, 2010

Smilin’ Jack
Smilin’ Jack
Watch out for Smilin’ Jack
He’ll cut your throat
or stab you in the back
-Traditional children’s rhyme in Iphos

The legends of Smilin’ Jack are confused at best, he may have been a pirate, a drunkard, an adventurer or even a spurned lover or any or all them.  What seems to be true is that he was found with his throat cut and buried in a pauper’s grave from which he clawed his way out of six days later.  Since then, he has preyed on high and low, favoring a cut throat as the way to dispatch his victim.

Iphosa Legends by Jokalin Rose of the University of Iphos

Smilin’ Jack                                                  CR 6 (2,400 XP)
CE medium undead
Init +8; Senses darkvision 60 ft.; Perception +17
AC 22 (+2 leather armor, +3 Dex, +5 natural armor, +2 Dodge)
hp 75 (10d8+30)
Fort +6, Ref +8, Will +8
Defensive Abilities channel resistance +4, DR 5/slashing, fast healing 1, resistance to cold and electricity 10, Resistance to fire 5, unkillable; Immune undead traits
Spd 70 ft
Melee MW razor +14/+14/+9 (1d4+3/17-20 + 1d3 bleed)
Special Attacks paralyzing smile, sneak attack +5d6
Str 17, Dex 19, Con —, Int 10, Wis 13, Cha 16
Base Atk +7; CMB +10; CMD 24
Feats Dazzling Display, Dodge, Improved Initiative, Weapon Finesse, Weapon Focus (razor)
Skills Acrobatics +14, Intimidate +16, Perception +14, Stealth +17
SQ bounding leap, supernatural speed
Languages common (but rarely speaks)
Environment any but usually in graveyards or near places of mass slaughter
Organization only one
Treasure Value 1,000 gp
Bounding Leap (Su): Smilin’ Jack can jump up as high as 25′ and up to 50′ across and he never takes falling damage.

Paralyzing Smile (Su): Seeing the cheerfully terrifying double smile of Smilin’ Jack with freeze the blood of even the strongest man.  To resist this requires a Will save (DC 17) or the victim is paralyzed for 2d4 rounds and slowed for 1 round thereafter.  Once this save is made one is immune to this effect for the next 24 hours.  This is a mind-affecting effect.  The save is Charisma based.

Unkillable (Su): Smilin’ Jack can be killed . . . for a time.  But unless his spirit is exorcized and his razor destroyed, he will return.

Supernatural Speed (Su): Smilin’ Jack is treated as being under the effects of haste at all time.  It is treated as if cast by a 10th level caster and if it dispelled, Smilin’ Jack can reestablish it as a free action.

Smilin' Jack's Razor

Smilin’ Jack’s Razor

Smilin’ Jack appears as a man in a long coat over blood splattered leather armor, he has a maniacal grin and his throat gapes open from where it was slashed.  His eyes are bright with madness and he uses a razor with surgical precision at blinding speed.

Smilin’ Jack is the sort of unkillable undead that is a very modern haunt but fits into legend as well.  He strikes in a pattern, that changes each cycle of attack, killing 4-7 victims and then vanishing until the next cycle begins.

What you may know about the Smilin’ Jack:
Knowledge (Local) DC 18.  Smilin’ Jack is a haunt and a killer who slashes his victims with a razor.  He appears on a schedule known only to him, killing in a pattern known only to him and then vanishing.

Knowledge (Local) DC 25.  Smilin’ Jack has been ‘killed’ several times over the years but he always returns.

Natives of Iphos gain a +2 bonus to these skill checks.

Before Combat: Smilin’ Jack stalks his victim, waiting for the perfect moment to strike.

During Combat: Smilin’ Jack is only concerned with his victim of the moment, his attacks will all be directed to that end.

Morale: Obviously, Smilin’ Jack has no fear of death.  He will flee combat when he has killed his victim, and maybe slashed a few others just to prove a point.

Notes: Figured I would end up the October monsters with a crazy mad slasher haunt.

Inspired by Springheel Jack and the Jack of Smiles from the delicious Echo Bazaar.  No insult to the heroic pilot, Smilin’ Jack, or the masked hero of the City of Gallery, Lavender Jack, is implied.

Image from Buffalo Valley Colonial Crafts.


  1. Very cool! This actually feels like it taps into a lot of things like the Gentlemen from the Buffy episode Hush and gives off a Candle Cove vibe as well. Very good stuff! I’m working on a set of brother NPC’s called the Shankhill Butchers (like the Decemberists song) for my Day After Ragnarok campaign. They’re a group of serial killers basically, and I think I may have to steal some of this for them!

    • Glad that it is useful/inspiring. It was an interesting haunt to build.

  2. Yeah, I like this a lot, and it hits a lot of targets, including Spring-Heeled Jack as well as the organization of Jacks from Neil Gaiman’s Graveyard Book. Love it.

Please share your thoughts

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: