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