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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
by Daniel Bonnizzio November 04, 2007

Words related to I Roll Twenties

arcade brahe i penny roll twenties tycho
 
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"
by Teflon Don Da Da© July 24, 2005