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A word which is defined as both itself and the opposite of itself.

E.G

“Because of their oversight, Russia was sanctioned by NATO”

Can mean that Russia was given approval (sanctioned) by NATO because of their vigilance (oversight)

Or that Russia was punished (sanctioned) by NATO because they egregiously overlooked something (oversight)
Words that can perform or imply two directly contradictory actions are called contronyms

1. I clipped (attached) on a bow tie after I got my hair clipped (detached, cut off) at the barber shop

2. The House Oversight Committee’s role is to perform oversight (strenuous watchdog duties) by ensuring that no oversights (mistakes, errors) are made in the government

3. I screened (blocked) the light from my eyes so I could see the movie that was being screened (shown)

4. I was the latest to rent (buy) the apartment that my landlord had been renting (selling, leasing) for five years now
Contronym by Alex-2598 March 23, 2021

Double Controversy 

a discussion in which opposing views are expressed where the view in question is also opposite of that window.
Man: If you are a virgin and you have sex with a virgin. What would you call that?

Other Man: That's a double Controversy
Double Controversy by Dr. Jelsier November 26, 2010

Air Traffic Controller 

A male who dates more than 4 women outside his 50-mile radius at one time. When it’s time to for the women visit his home city he then becomes an air traffic controller.
Air Traffic Controller: A male who dates more than 4 women outside his 50-mile radius at one time. When it’s time to for the women visit his home city he then becomes an air traffic controller.

Jim has poon in almost every city on the east coast. You should see him at the Holidays he’s like an Air Traffic Controller. “Becky your clear to take off on runway 6” roger, “Linda clear to land runaway 2” out.
Air Traffic Controller by Bent Spear September 11, 2006

PS3 Controller 

The PS3 controller looks exactly like the PS2 controller, no longer vibrates, has really crappy "motion sensors" which only a few games will use, and is wireless.

Sony will not be losing 50% of their female market because of the lack of vibrating, anyone who makes that joke is lame. Controllers shouldn't go there.
Those guys at Sony are so incredibly original. Making the PS3 controller look exactly the same as the PS2 controller.

controler whore 

is someone who doesn't give up the controler to a game when his turn is over, he just keeps it to himself like a whore.
dude he is being such a controler whore he's turn has been up three times ago, bitch
controler whore by budman2000 July 22, 2009

controlling-ness 

Describes the act of trying to control someone else.
Protectiveness is fine as long as it doesn't veer into controlling-ness.
controlling-ness by rynn23 November 19, 2010