- "Chaos (or Chaotic) is the opposite of Law. It is the belief that life is random, and that chance and luck rule the world. Everything happens by accident, and nothing can be predicted. Laws are made to be broken, as long as a person can get away with it. It is not important to keep promises, and lying and telling the truth are both useful."
- "To a Chaotic creature, the individual is the most important of all things. Selfishness is the normal way of life, and the group is not important. Chaotics often act on sudden desires and whims. They cannot be trusted, and their behavior is hard to predict. They have a strong belief in the power of luck. Chaotic behavior is usually the same as behavior that could be called 'evil'." -2nd edition 
Below is a detailed guide of what The Nameless One can say and do in order to become Chaotic.
In order to become Chaotic, The Nameless One should:
- Lie and bluff
- Break vows
- Join the Anarchists or the Xaositects
- Be impulsive: taunt Morte, have conversations with skeletons, zombies or bark at madmen
Note: The values for alignment are hidden in Planescape: Torment. Qwinn's Tweak Pack has a component called the Scale of Souls, which, if installed, allows the player to view alignment values. The Nameless One starts the game with a "Good" and "Law" rating of 0, signifying neutrality. Chaotic acts subtract from the "Law" value, and when the rating reaches -21, the alignment changes to Chaotic; when it reaches 15, the alignment switches to Lawful.
- Taunting Morte about being a simple skull
- Lying to Vaxis?
- Attempting to engage the skeletons in conversation.
- Admit waking up on a Slab upstairs to Soego.
- Lying to Deionarra, saying her name sounds familiar. (Also increases Evil)
The Hive, Mortuary AreaEdit
- Lying to Sev'Tai, telling her the thugs are dead when they haven't been killed.
- Bluffing when accusing Annah of giving the wrong directions to Pharod.
- Commenting on how much better TNO looks compared to "The Post".
- Threatening Wife-of-Angyar (Also increases Evil)
- Signing more than one Dustmen Contract with Mortai, Emoric and Old Coppereyes.
- Threatening Mortai into relinquishing Angyar's contract with a bluff.
- Lying to Emoric, saying TNO believes in the Dustmen philosophy when he doesn't.
- Telling Emoric the truth after promising Pharod TNO's silence.
- Lying to Emoric on Pharod's behalf.
- Lying while taking the oaths to join the Dustmen faction.
- Telling Awaiting-Death: "Truth: Well, considering that death and I aren't on speaking terms anymore, I considered it a no-lose proposition."
- Taking Awaiting-Death's money and leaving without killing him. (Also increases Evil)
- Actually killing Awaiting-Death. (Also increases Evil)
- Saying "a bunch of fun-loving dustmen" when Sere asks "what do you see".
- Lying "out of kindness" about Sere's looks. (Also increases Good)
The Hive, Smoldering Corpse AreaEdit
- Growling and snarling at Barking-Wilder, joining the Chaosmen faction.
- Threatening the Damsel in Distress with a bluff after seeing through her act.
- Howling or snarling with the Barking Dog Thugs.
- Replying "It doesn't really matter." when Mourns-for-Trees asks how TNO is.
- Telling Mourns-for-Trees that "all things die".
- Lying to Mourn-for-Trees when he asks for help.
- Lying to the thugs outside the Smoldering Corpse Bar to get Porphiron's prayer beads back.
- Arguing with Dak'kon that the city is not flawed as something need not be ordered to have a purpose.
- Lying to Alais.
- Agreeing with Ilquix.
- Lying to Ilquix.
The Hive, Marketplace AreaEdit
- Lying to Ash-Mantle concerning the bar and asking for money (also increases evil)
- Lying to Ash-Mantle, saying TNO doesn't know where the bar is if he has already visited it. (also increases evil)
- Emphasizing that TNO will let Ash-Mantle *live* (Bluff) after he tries to run and TNO catches him
- Asking Ash-Mantle more than one question after vowing to let him go, after he tries to run and TNO catches him.
- Bluffing when deciding Ash-Mantle's fate.
- Laughing at the Crier of Es-Annon when he pays after TNO demands payment (also increases evil)
- Lying to Reekwind, telling him TNO has no money for his stories.
The Hive, Northwestern AreaEdit
- Lying to Fleece, telling him TNO knows where his aunt lives... for a price (also increases evil)
- Telling Fleece what he really meant was a local brothel.
- Attacking Fleece after he is caught stealing (also increases evil)
- Lying to Porphiron about the methods used to get his prayer beads back.
- Lying to One-Ear to get Nestor's fork back.
The Hive, Alley of Dangerous AnglesEdit
The Hive, Ragpicker's SquareEdit
- Lying to Marrow-Friend.
- Lying to Old Mebbeth, telling her his name is Adahn.
- Lying to Nodd, telling him his sister is a servant in a tavern. (Also increases good)
- Lying to Nodd, telling him his sister is a foul whore. (Also increases evil)
- Lying to get out of giving Nodd his sister's money. (Also increases evil)
- Having spent Amarysse's money instead of giving it to Nodd.
- Bluffing after catching Yellow-Fingers when he tries to steal from TNO.
- "Throwing" TNO's voice with Marta.
- Lying to Marta, telling her TNO is the one expecting her delivery.
- Suggesting Radine make her own number.
- Lying to Ku'u Yin
Pharod's Court Edit
- Lying that TNO will not tell anyone about where Pharod is getting the bodies.
- Vowing not to tell anyone about where Pharod's getting his bodies, and subsequently telling Emoric and/or Sharegrave.
- Lying that TNO won't kill Pharod if he doesn't like his answers. (Also increases evil.)
- Bluffing, threatening Pharod to hand over TNO's belongings.
- Refusing to submit to the undead when entering the area. (Also increases evil.)
- Promising not to tell the answer to Riddling Skeleton's riddle, but telling it to the Puzzled Skeleton anyway.
- Telling Acaste that TNO's name is Adahn.
- Telling Acaste that the Silent King is really dead. (Also increases evil.)
- Vowing not to tell anyone about the Silent King, then breaking the vow.
- Lying that TNO will not reveal the Silent King's fate.
- Telling Many-as-One about the Silent King's secret, if TNO has previously vowed not to. (Also increases evil.)
- Lying to the Dabus about how the other Dabus died.
- Morte is Chaotic Good.
- Annah is Chaotic Neutral.
- Ignus is Chaotic Neutral.
- Nordom is Chaotic Neutral.
- ↑ Gygax, Gary; al., Dave Arneson ; edited by Tom Moldvay ; illustrations by Jeff Dee ... etc. (1981). "Dungeons & dragons : fantasy adventure game : basic rulebook". Lake Geneva, WI: TSR Hobbies. Template:Citation/identifier.
- ↑ Qwinn's PS:T Tweak Pack readme, detailing how the Scale of Souls component works, as well as alignment ratings.