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Coach Z fits this trope. He loves to rap (badly), and uses dated slang.
Parodied on Homestar Runner, in Strong Bad Email #164, 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 SBEmail #197, Strong Bad panics over not being cool. His idea of having "edge" are basically self-destructive and oddly passe. Even Strong Sad takes advantage.