roll a twenty

When you completely fluke out and do something perfectly through dumb luck. The term is derived from the roll playing game Dungeons & Dragons in which rolling 20 on a 20 sided dice guarantees success at whatever your attempting.
"Dude, did you see Jimmy get hit by that car? He flipped over the hood and landed on his feet!"
"Shit, way to roll a twenty on his acrobatics."
by Lvl20warlock November 23, 2007
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roll a twenty

rolling an entire 20 bag of weed in one joint (UK)
"can i skin up with ur weed". "yeah man roll a twenty i got another bag here"
by Lee Parker April 13, 2008
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Rolling Twenties

This refers back to the "Roaring Twenties" 1920 when Prohibition of alcohol started. Only this century it's the many State's legalizing of marjauna starting Jan 1, 2020.
Everyone can roll legal joint's in the "Rolling Twenties"
by sparkyboy June 02, 2019
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I Roll Twenties

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.
by Daniel Bonnizzio November 05, 2007
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I Roll Twenties

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 25, 2005
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rolling a twenty

In Dungeons and Dragons, it’s when you make a perfect roll and everything goes right, most of the time, if your DM isn’t awful. DND players use this term to describe a total victory in real life.
Jumbo: Boy I’ll tell you what, that girl went home with you RIGHT QUICK!

Vishnu: I cannot help it, I was rolling a twenty in diplomacy.
by Sharpguyinatie December 04, 2017
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