* Parodied a number of times on ''WebAnimation/HomestarRunner'':
** Coach Z fits this trope. He loves to rap (badly), and uses dated slang (which tends to be furthered mangled by [[WhatTheHellIsThatAccent his outrageous accent]]).
** In WebAnimation/StrongBadEmail #164, [[http://www.homestarrunner.com/sbemail164.html looking old]], Strong Bad fears he's losing the "youth vote" of "young parsons who eat their yogurt through a tube", and thus calls an "emergency marketing meeting". The Cheat suggests frenetic, MTV-style editing, while Bubs thinks adding a lowercase "i" to the front of words is a good idea. Ultimately he undergoes a "lace-lift" which results in the opposite of the intended effect so that he ends up looking and sounding like his own great-grandmother.
** In [[http://homestarrunner.com/sbemail197.html SBEmail #197]], Strong Bad panics over not being cool. His ideas of having "edge" are basically self-destructive and oddly passe. Even Strong Sad takes advantage of it.
** Acknowledged yet avoided by the [[http://www.homestarrunner.com/tgs11.html Teen Girl Squad]], as their TotallyRadical slang is so ridiculous, it can't be anything but fake.
--->'''Cheerleader''': Okay, my Spanish Galleons!
** Their 2010 April Fools gag is a TotallyRadical revamp of the characters with XtremeKoolLetterz. They're revamped for the nineties...a decade or two late.
** [[http://www.homestarrunner.com/2manyknives.html An Important Rap Song]] is entirely made up of a middle-aged voice actor trying to deliver a 90's style cartoon PSA. The ''basic concept'' is outdated, never mind the lyrics.
* Several of the "Awesome" videos on Newgrounds use this trope for comic effect with characters such as Sonic and Gray Fox. "Yo yo yo B-boy [[Franchise/MetalGear Snake]]-Dawg-G..."
* [[http://www.sickanimation.com/cartoon.asp?name=coolcourt My client has the right to life, liberty, and the pursuit of chilling out!]]
%%* ''WebAnimation/TheLebrons'' is built on this trope, primarily due to being aimed towards African-American audiences.
%%* In ''WebAnimation/LuckyDayForever'', the Whites's society is built on this trope in an attempt to show that their way of life is desirable.