Here is the full list of all 27 The Crooked Man achievements.
Beat the game twice
Beat the game once
Beat the game without drinking the energy drink
Get Bad Ending 4
Get Bad Ending 3
Finish Scene 4
Finish Scene 3
Don't miss a single shot at the Crooked Man
Get Game Over 5 times
You shot Fluffy
Read the books in the hospital day-room
Try to enter the bed next to D's bed
Get killed by poison gas
Get Bad Ending 2
Defeat the Crooked Man in Scene 1 without taking any damage
Finish Scene 2
Defeat the Crooked Man in Scene 2 without taking any damage
Try to enter D's bed
Escape the gas with over 1 minute to spare
Get Game Over once
Read the books in the school
Get Bad Ending 1
Finish Scene 1
Survive first encounter with the Crooked Man
Read the books in the hotel library
Finish the Prologue
Go back to bed without answering the phone