1. Conjure hilarious critical fails
    If you critically fail a perception check, you deserve to poke your eye out and lose the ability to make any more perception checks
  2. Make the adventurers doubt whether they really have any incentive to save the princess
    "She's an androgynous prude and isn't really that rich or attractive in the first place, but she IS a princess so you're probably obligated by law to do something"
  3. Give the monsters an extra AC just to watch the players suffer on their rolls
    Watching the third defense in a row is so satisfying
  4. Make up dumb reasons why the player failed a check
    "Your ass is fat so you got stuck in the window when you tried to dive through"
  5. Create hilarious magical items and don't tell them what they do
    The Immovable Rods stay in place no matter how much force is applied to them unless you toggle the button on the end. Known to trigger accidentally.
  6. Intersperse hilarious useless items and don't tell the players what those do either
    The Ring of Sobriety is nonremovable and prevents you from consuming any alcohol by giving you overwhelming feelings of guilt.
  7. Inflict inconvenient curses on the players
    When you have astigmatism and a monacle on the wrong eye, it can get annoying tripping about once per encounter.
  8. Make the players act out all of their dialogue
    Somehow actually having to convince the shopkeeper to give you a discount because you have a large chest is funnier than just saying it.
  9. Add ridiculous puzzles to the dungeon
    What do you mean that Sudoku isn't how you planned to spend your Friday night?