The term "Roofless" is used to define two (2) types of people:
1. Acknowledge someone who has the ability to make very harsh & demeaning personal insults against another person and not have any remorse, instead basking in the glory. (see example 1)
2. Praise a person before or after a dare, to whom the person is willing to take a huge risk that is highly embarrasing to themselves or another person. (see example 2)
When applied in a real-life situation, it is spoken or shouted AFTER the person has made the comment or accepted/completed the demoralising challenge (as given in the example).
Jack: Hey have you guys seen the new Terminator movie?
Daniel: No, but have you seen the one starring you in it?
Daniel: ITS CALLED THE VIRGINATOR!!
Everyone Else (to Daniel): ROOOFLESSSSSSS!!!!!
Everyone: Oy go steal that bottle of water and take a picture of yourself with it.
Jackson: I'm not going to do that...
Jackson: Everyone would know what that is... except Jack...
Everyone (except Jack): ROOFLESSSSSS!!!
Jackson: YOU KNOW WHAT, FINE! I'll steal it.