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  • An interesting intercom conversation:
    Intercom voice: Who is it?
    Caleb: Everybody dies!
    Intercom: Reeeally? Cool! I'm buzzing you in!
  • Because of the game's glitchy nature, killing low-level grunts in mid-threat doesn't stop them from shouting at you, even if gibbed:
    "You're dead! Do you- *KA-SPLORP!* -hear me?! DEAD!!"
  • The Ancient One attempts to play some mind-games on Caleb by possessing the original (now dead) bodies of the other three Chosen. It backfires.
    Caleb: Aww, you're gonna hurt my feelings.
    • He also tries to deliver a dramatic villain speech about undoing all reality, and retroactively eliminating the past, only to realize he has no idea what's supposed to happen to the future. Caleb patiently lets him finish hesitating, even egging him on with an impatient "Well?".
  • Standing idle while holding the Voodoo Doll weapon will cause it to sit up in Caleb's grasp and cheerfully wave at the player. It's equally adorable and creepy.
  • This exchange is always good for a giggle:
    Caleb: The choice is yours: Walk now and live, stay and die.
    Cabal Goon: I'm staying!
    Caleb: (cheerfully) Then you're dying!
  • Cabal members aren't the only ones that throw insults Caleb's way - Choking Hands, upon spotting the protagonist, will take the time to flip upside down, land on their wrist, and give him the one-finger salute before they start chasing him.
  • The "JoJo's Big Adventure" level from The Nightmare Levels expansion is pure Black Comedy. Starring Ishmael who was coerced to take the role of said JoJo - The Idiot Circus Boy and how he slaughtered his way out of his imprisonment. On top of that Ishmael is by far the most clever of the Chosen and offers a gleefully sarcastic snarky comments on whatever depraved stuff he encounters in the freak show. He's even able to make fun of his own misery and it doesn't deter his charm a single bit.
    *when entering the Merman's tank* "Ahh, the catch of the day, I presume."
    *in front of the Love Tunnel ride enterance* "There is most definitely no love in this tunnel."
    *at the sight of half-man-half-woman having been sliced apart* "Oh my, looks as if they had to split."
    *after finally getting out of the place* "Well, that wasn't so bad. I wonder if I'll ever miss the smell of my own dung mingled with hay."
  • According to Gideon, Caleb spent the years since the first game "hanging out in dive bars, swilling cheap beer, smoking bad cigars, starting brawls over women of dubious moral character." Caleb's an undead, gunslinging cultist and apparently a complete bum too.

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