The Photo ShootPut one of the victim's hands in their pants. In their other hand, place any publication that isn't usually considered porn. (Hint: any obscure hobby or children's magazine should yield hilarious results.)
Generation ShameCall the victim's parents and share their most incriminating stories. If you're really trying to make someone feel ashamed, this is the most direct route possible. No point beating around the bush.
The GotyeTake off their clothes and paint their body so they blend in seamlessly with the background. Now they're just somebody that you used to be awake with.
Fly on the WallTape them to the wall inside a duct tape "cocoon." Make sure to leave air holes. Unless you really don't like the person.
WhodunitPut a bloodied dog collar and a ski mask in their pockets. When they wake up, tell them tearfully that a drunk maniac in a mask killed your puppy last night. See how long it takes them to confess.
The UrkelSet up a bunch of fake Twitter accounts and bombard the victim with furious complaints about their offensiveness and insensitivity. When they wake up they'll be forced to wonder, "What did I do?"
The Wet DreamSee how directly you can interfere with their dreams without them actually waking up. Whisper sweet nothings in their ears, place a damp washcloth against their lips, and after a while, douse their crotch in water. If you have done this correctly, they have just had a sex dream to completion.
Into the AfterlifeDangle the victim out the window and take a picture. Post it on Facebook alongside regretful reports of their death. Next, remove all furniture and decorations from the room and refurnish it in a theme of fiery crimson and torture instruments. See how long you can make them think they are actually waking up in Hell. (It helps if you have a good Devil impression.)