Driller/Drilla can be used in many ways. Driller or as most UK slang users would say drilla, (they do not pronounce the r in this word- unless they are posh) the grammatical definition is a gang member or shooter or aggressive invader. Although many people in the UK- mostly England will use it as a greeting to a friend or an affiliated gang member.
In a second terminology it can also be used in Chicago as the is the word and phrases origin. In chicago it can also be used in the same way as the UK but is often pronounced with an r. The first way it was used was "One who shoots with no target in mind". This implies that it was a term for drive by shooters or people who were ruthless with a gun. Some people may use the two variants of the word with a 'my' infront of it to show there part of my gang or they are my friend.
UK Friend 1-Whats good my Driller/Drilla
UK Friend 2- Notin my g
Uk/Chicago gang member 1- Whats good my Driller/Drilla
Uk/Chicago gang member 2- I'm just bouta shoot them on the other block.
by Yœőøöõôóòo February 26, 2023
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The act of having sex with your clothes on. (The girl wears pants with a fly, or the man cuts her pants out.)
I did the Detroit Driller with Rebecca last night. I wore my special polo shirt for the occasion.
by The man dan with a plan December 3, 2018
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A killer driller is a penis so big/long that it causes immense pain to the woman receiving it up to the point of bleeding
(Betty) OH MIKE THAT KILLER DRILLER Is TOO BIG! PULL IT OUT!
by Heracronite2003 August 4, 2016
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A white man who dates/marries a black woman
They are often called that by racist white men and women
WW: OIL DRILLER

WM: Man stfu.
by ISHFWILF October 30, 2018
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When you have sexual intercourse doggy style and as the girl climaxes you simultaneously snot rocket on her back.
Lil susie rotten crotch was shocked when Bertonio decided to give her the Driller's Mud
by Booger_1337 December 17, 2008
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When two friends are having relations with a girl in a large freezer and one ejaculates on her mouth, eventually forming a frozen layer of semen on her mouth. The other friend then pokes through it with his penis.
I finally broke through with the arctic driller!
by Gdawg2144 February 5, 2010
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Making a nude women do a tripod and then, pushing the penis straight down, moving your penis in and out of her vagina while also rotating around and stepping over her upturned legs.

The man can also be wearing roller skates if done on a hardwood floor.

"Dude, what happened last night in Hoyme dorm?"

"I totally gave her the oil driller but then she passed out"
by BigRob02 February 12, 2008
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