- Alternate Aesop Interpretation: Essentially, the theme of the game is Hard Work Hardly Works and focuses on how to cope with disappointment, but there's room to interpret the finer points:
- It's pointed out that D should take the Bar exam again, but be prepared to seek other options if it doesn't work out, meaning that working hard for a dream is only a problem if you don't take care to have a backup plan just in case.
- Forgetting a relationship isn't the same thing as letting go of one. Forgetting someone is s coping mechanism, a disservice to yourself and your past that means you'll never be able to cherish the good times or learn from your mistakes, while letting go is simply choosing not to cling to the past and hope for a future you already know you'll never have.
- Fluffy's arc can be summed up as "accept help when it's offered, even if it's not the help you want", since Fluffy is searching for his mom and rejects Dave's aid at every turn.
- Family-Unfriendly Aesop: Most stories go the "Never give up! With enough hard work and dedication, you'll achieve your dream!" route. This one doesn't. The moral of the story is that sometimes, hard work and dedication to a dream is just bashing your head against a wall, and the harder you work toward something impossible the more miserable you'll make yourself. Sometimes, you have to give up on one dream... so that you don't give up on living altogether.
- Good Bad Bugs: You can actually pause the game during the fighting sections with the Crooked Man, and if you select an unusable items, the game will think you're swinging the weapon. Very useful if you don't want to deal with the Crooked Man. Just don't go over the number of times you're supposed to hit him or he'll become impossible to defeat.
- In the second fight, you can hit the Crooked Man through a table, so all you need is get him trapped on the other side of a table and start swinging until he's dead.
- You can do it during first fight too. Just get yourself behind sign near the piano, the Crooked Man on the other side and earn easy win.
- Harsher in Hindsight: Later on in the game, you find out that Paul has the ability to see and sense the paranormal. He knew from the beginning that something was off about the room, but didn't mention it to David and let him move in there anyway, which directly led to all the events of the game.
- Hilarious in Hindsight: After getting her out the hotel, Sissi gives a small kiss to Dave. Cut to later in the game, we find out she is a Literal Split Personality of the very male Duke. Which means that Dave was kissed by a dude, and liked it. May become creepy when you follow that line of reasoning to realize that Duke is the Crooked Man, which makes his chasing you more than a bit eerie.
- Insane Troll Logic: Uri's games have a general trend of forcing you to choose the LEAST realistic option during a choice scene in order to get the best ending. In The Crooked Man, you attack people on the brink of committing suicide, tell people to give up on their dreams, and tell people that it's bad to let go of the past. Realistically, none of these would give a good response. Justified for this game in that you are dealing with the ghost of a person who simply wants to be told the hard truth, and a malicious spirit that will not listen to reason.
- Jerkass Woobie: D. He's got an incredibly rude and snobby personality, but we learn over time that he's become that way because he's been trying and failing for years to become a lawer, something he's wanted to do since he was a boy, and has received nothing but mockery and scorn for it. The fact that he softens up eventually definitely helps. If you get his bad ending, however, stabbing David in a fit of frustration and despair kind of loses him this title.
- Nausea Fuel: The dead cat, the Crooked Man eating a model of an embryo (it was fake, but still), the Crooked Man's impossibly cricked neck...
- That One Boss: The dodgy fighting mechanics are difficult to use due to the fact you need to stop moving in order to hit The Crooked Man, while all The Crooked Man needs to do is touch you to hurt you.
- Paranoia Fuel: It is heavily implied by certain elements of the game that although the Crooked Man "locked onto" Duke and David, it wasn't actually created by them. It, or other beings like it, exist independently waiting for people susceptible to its influence that it can drive to suicide or kill.
YMMV / The Crooked Man