Funny / Cry of Fear

• The secret ending, when it turns out that the one who hit Simon with his car is none other than David Leatherhoff, stoned off his ass. The fact that he's still in the graphical style of the original mod, and he still speaks only in text makes it even funnier.
• The Scream trailer showcasing folks such as PewDiePie, and Jack and Brad from 4Player Podcast getting scared.
  LEROOOOOOOY JEEEEEENKINS!
  *Swedish cop goes flying*
• Simon's voice acting can be funny at times, especially noticeable when watching Youtube Let's Plays.
• When you pick up the secret weapon, the FAMAS, Simon gags and yells "FRENCH!" in disgust. The FAMAS is a French assault rifle.
• While looking for two fuses, Simon comes across a flooded underground room with tons of enemies that are avoidable. If developer commentary is enabled, there's a small speech bubble in the corner of the room opposite the exit, surrounded by enemies that will attack if you get too close. All it says is "hello!" before throwing you back into the action.
  • Similarly, there is the commentary found at the start of the first Nightmare Sequence.
    ruMpel: I don't wanna tell you why I made this. Uh. I-I really don't I-I don't-I don't think so. No, no. Uh- I really don't. Th-This-This is too much. No, no, no. Really no. NOOOOO! Fuck you!
• Before fighting the Carcass, open up the console and type "sv_joebiden 1". Congratulations! Carcass now fires Joe Biden cubes at you.
• A lot of the game's moments like Simon confessing to Sophie or curb stomping the Doctor to death can be mitigated on a repeat playthrough if you have Simon wearing the pink Hello Kitty outfit.
• The 4th ending sees Simon confront his book's manifestation of himself, all while the latter is using the various weapons you obtained throughout the game to kill you. One of the weapons in particular is the MP9, which cannot be obtained in the game... unless you donate $10 to Team Psykskallar. This means that Book Simon was so desperate to kill his real counterpart, that he resorted to using a Pay to Win weapon to do so.