- The Witty Banter between Garcia and Johnson provides much of the humor.
- If you get caught by the huge demons in the Sniping Mission, they'll grab you and chuck you through the back of the nearest billboard, where your head pokes through a rather embarrassing part of the other side, with Garcia having the dopiest look on his face.
- Johnson during The Stinger.
- The moment Garcia gives up and accepts the weirdness of the Underworld:
Johnson: These human hearts let you withstand the darkness longer.Garcia: I'm not even going to ask how that makes sense.
- When you buy from Christopher after the part where Paula repeatedly drowns.
Christopher: Aw, my heart goes out to the gal with the flotation issues! *rimshot*
- Garcia and Johnson come across a decapitated, demonic version of Paula, who picks up her head and twists it, violently, back onto her neck. Johnson's response?
Well, that killed my stiffy.
- Anything that involves the "Big Boner".
Funny / Shadows of the Damned
Suda51's surreal dark sense of humor pervades this game.