What is I Roll Twenties?
1.
Slang term similar to saying "I am awesome at everything."
Stems from the proud nature of D&D-style games where rolling a Natural 20 (a twenty straight from the die) is considered a great skill.
"That is because I roll twenties." - Tycho Brahe, Penny Arcade
See
2.
The proudness of rolling twenty sided dice, referring to someone who Plays D.A.D./ Dungeons and Dragons. The term originate's from the web comic Penny Arcade.
"That is because I roll twenties"