I kind of like this! I think that you might want to consider the fact that the character is set up to be a dickweed to the other player characters. The normal assumption in AW is that 'We are currently allies at the beginning of play'. If your Hx rules state that two players know how much of a dickwad you are, it seems to subvert the normal assumption. Maybe you might want to consider providing an out for that.

Reword the Hx options to be more positive, hmm?

The character theme seems to be a generally deceptive character that also has some potential professionial gambler/cheater theme. However, because the professional gambler/cheater parts aren't super strong, I think it'd make more sense to have Card Shark be an optional move as opposed to required move.

A valid point. Actually, if I am not mistaken, there was a strongly-weird playset about gambling-centered character, so moving it more to a background here might be a nice move.

I'd change Sweet Lies to mirror Oftener Right/Insight/Eager To Know: If you give a character false information and they act on it, they take +1 forward, and if they fail at what they were attempting to do, they mark experience.

What do you think about the version I posted in comments above?

I think Sucker is Born Every Minute is kind of boring and leads to unnecessary +1 proliferation. Think of the gentle +1 ecosystem! To some degree, I think the people who see you coming should be the PCs, particularly the PC's with high Hx, and the interference rules already cover how that effects manipulating PCs.

Dropping "The sucker..." might solve the hot advancement problem. The sex move would then use "Sweet lies", as you said. But I think it would be cool to have a betrayal-based move. How could it work?

I think "I can explain" isn't worth the cost of a move as written. Maybe change it to a generalized "When you manipulate people to clean up your own mess, get Neat Thing"

There was a nice move from Ewen Cluney's Dragon World which worked somewhat like that. Might be worth to hack it.

So, I've been lately working on a playbook for a sort of a grifting and manipulative character and decided to drop the alpha version here.

Introducing... The Smiler

Among grimness, depression and poverty, people want to be told that they are loved, that they can win big, that there is a way out, a hope, a chance of something greater. People want to see a smile on a friendly face.

In Apocalypse World, smiles often hide the shark's teeth.

Choose name, look, stats and etc...

Sex: man, woman, ambiguous or transgressing

Name:

Chance, Blackjack, Doyle, Rook, Vegas, Harley, Hustle, Joker, Clubs

Switch, Face, Dice, Karma, Hoyle, Dame, Shuffle, Eleven

Eyes: fox eyes, cold eyes, calculating eyes, playful eyes, quick eyes, paranoid eyes

Face: open face, pretty face, trustworthy face, grinning face, cute face, kind face

Body: slim body, fat body, compact body, gorgeous body, soft body, battered body

Clothes: casual wear, travelling wear, luxe wear, worn wear, formal wear

Hx
Everyone lists their characters by name, look, and outlook. Take your turn.

List the other character’s names.

Go around for Hx, on your turn:
Tell everyone -1 - you are one lying cheating bastard

On the other’s turns, choose 1, 2 or all :
- One of them was cheated by you. Tell that player Hx+2.
- One of them mistrusts you, knowing well what are your true motives. Thel that player Hx-1.
- One of them pulled you out of tough situation. Tell that player Hx+1.
To everyone else, +1. Knowing people well is your bread and butter.

Stats:
Choose 1:
Cold +1, Hard 0, Hot +2, Sharp +1, Weird -1
Cold +1, Hard -1, Hot +2, Sharp +1, Weird 0
Cold 0, Hard -1, Hot +2, Sharp +2, Weird -1
Cold 0, Hard 0 , Hot +2, Sharp 0, Weird +1

Moves:
You get all the basic moves and Card Shark. Choose 2 additional Smiler moves.

Smiler moves:

Card Shark
When you gamble, roll+hot. On a success you win. On a 10+, choose 3. On a 7-9, choose 2.
- you win something extra, be it a bonus barter or overheard info
- they don't get angry
- they don't get suspicious
On a failure, you'll get accused of cheating even if you didn't do anything like that (did you?)

Sucker is born every minute
When you meet someone important (MC's call) who isn't familiar with you, take +1 forward when you cheat or betray them.

Pretender
When you are pretending to be those who you're not, roll +hot. On a 10+, they believe you until there's a clear evidence to the contrary. On a 7-9, choose:
- they believe you now, but will double-check your words later
- they will need additional proof
- they won't believe you, but otherwise you are free to go
On a failure, they get suspicious: they may confront or accuse you. Take -1 forward against them.

Sweet Lies
If somebody acts upon one of your lies, they take +1 forward. If it's a player, they could mark experience instead.

Wanderer
When you first enter a settlement, roll+sharp and hold. At any time, you may spend this hold to:
- spend one hold and ask one question about this place or its inhabitants like if you opened your brain to psychic maelstorm
- drop all hold and find an escape route, like if you rolled 10+ on that forgot-how-it-was-called escape move
On a failure, turns out they still remember you. And not for something nice.

I Can Explain
When you seduce or manipulate someone, you may fail to futfill their condition once and they will hold you no ill will.

Sucker Punch
When you go aggro on the unsuspecting or distracted opponent, roll +hot instead of +hard.

Smiler Special
When you have sex with someone, you get to use the sucker is born every minute move, even if you don't have it and/or they are familiar with you.

Gear:
You get
* 1 backup weapon
- .38 revolver (2-harm close reload loud)
- 9 mm (2-harm close loud)
- hidden knives (2-harm hand infinite)
- sawed-off (3-harm close reload messy)
- stun gun (s-harm hand reload)
* choose one: lucky deck of cards, worn deck of cards, indecent set of cards, tarot deck, mahjong set, or bag of oddly-sided dice
* 2-barter from your past exploits

Advancement:
* Get +1 cool (max cool +2)
* Get +1 hard (max hard +2)
* Get +1 cold (max cold +2)
* Get +1 weird (max weird +2)
* Get a new Smiler move
* Get a new Smiler move
* Get 2 gigs (detail) and Moonlighting
* Get followers (detail) and Fortunes
* Get a new move from another playbook
* Get a new move from another playbook