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From the movie "Oldboy" based from the Japanese Manga of the same name. Definition: "To have sex with your daughter, and you don't even know it while cutting your tongue out and getting hypnotized thinking your daughter is your lover."
You sicko! You are an oldboy!
oldboy by L. Sosodef April 8, 2005
A term used to describe a man who fucks / fucked him daughter. The word is derived from the cult classic korean thriller named Oldboy , in which the titular hero Oh-dae su bones his daughter mido.
Mike :- Do y'all know that Greg fucks his big tit daughter?
Dave:- Really? I never could've guessed he's an Oldboy , Lucky fucker.
Oldboy by smooldikk September 25, 2019

Rum Old Boy 

An expression used to describe a camp, narcissistic, eccentric, quirky chap/individual or member of the establishment in satirical humour or derogatory fashion.
Nigel: “How’s the new bloke?”
Damian: “He’s a very Rum Old Boy!”, **laughs
Rum Old Boy by Cricket Buff August 7, 2011

Old Boy's Network 

An informal system by which money and power are retained by wealthy white men through incestuous business relationships. It is not necessarily purposeful or malicious, but the “Old Boy’s Network” can prevent women and minorities from being truly successful in the business world. It entails establishing business relationships on high-priced golf courses, at exclusive country clubs, in the executive sky-boxes at sporting events, through private fraternities or social clubs (such as the Free Masons), et cetera. These are arenas from which women and minorities are traditionally excluded and thus are not privy to the truly “serious” business transactions or conversations. A business person who does not travel in these elite circles of influence will miss out on many opportunities.
example of the Old Boy's Network at a sporting event:

"Yeah, I just saw Chuck at the country club the other day. You know Chuck. His son goes to school at Saint Andrews with your Mason brother Senator Northcutt's son. Anyway he told me he was interested in selling the R&D division at Imogen. I thought you might be interested..."
Old Boy's Network by DarkEnigma April 25, 2006
positive term of address used to connote respect, wisdom and experience in a person, usually male who appears youthful
"What's goin' on old boy?"
old boy by thickduff December 21, 2004

14 Year Old Boy 

A 14 year old boy is an upgraded form of a 13 year old boy. There are many types of 14 year old boys. One example is the "computer" version. This version will usually try to act highly intelligent and usually ends up failing horribly at it. It will act like a complete retard, trying to troll while looking mature at the same time. Another form is the "Gangsta" version. 'Nuff said.

Many of the users on popular sites like "Encyclopedia Dramatica" are of this age. And 15% of the viewers of pornhub are 14 year old boys.

They will also use forced memes at least 100 times a day, and usually use profane vocabulary.
*Adults are talking and make a joke*
14 Year Old Boy: Hahahah! That's classic. *Tries to act like he gets it*
*Adults laugh at him, and he thinks that they aren't*