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1.
A nickname given to the goggle wearing leader in each season of Digimon.
"Taichi, Daisuke, Takato, and Takuya are all Goggle Heads."
by Jijimon July 26, 2004
 
2.
A fan of the Japanese manga/anime "Digimon" (Or, briefly, a fan of Joss Whedon's "Dr. Horrible's Singalong Blog", until he realized that the term was already taken)
Jason had a Digimon-themed graduation party? Man, what a gogglehead.
by Agent Bumblebee August 06, 2008
 
3.
Insult, originating from the anime Digimon. Each season of the show contained a stubborn or bullheaded "leader" character who wore goggles on top of his head. The word "gogglehead" came to epitomise the stereotypical blunt, stubborn, or self-centered characteristics of the show's main characters.

Despite the fact the Digimon show has been over and done with for some time, it still has a pretty hardcore fanbase, and the word is common on website and forums that still cater to Digimon fans, as well as other "kiddie anime" sites that host pages about Pokémon, YuGiOh, or other shows that shared a fanbase with Digimon.

Often used affectionately.
That newbie didn't even read the rules before she started posting. What a gogglehead.

Tai always was my favorite character. I miss that old gogglehead.
by Lady Chevalier August 21, 2005
 
4.
A gogglehead is an organism native to rich and dense suburbian areas, specifically in bubbles (Irvine, Newport, etc.). Goggleheads are best described as a human-like looking animals with large black circles around the area where the eyes are supposed to be. The circles might have some slight variation in shape.
The first Goggleheads were first thought to start only with females. Observers saw the size of the black circles grow over a period of five months, and once it got large enough, they were declared a whole new species, Gogguleus Gigantius. Once adaption occured over all highschools, the species soon spread to middle schools and to mothers, specifically milfs. From there, the species spread to vulnerable males.
It all started as a curious and peculiar growth of a unique species, but as of late, it has turned into an uncontrollable epidemic, and in the eyes of the Department of Fish and Game, is a problem to the enviroment. To solve this, they have delcared an open season for Goggleheads.
"Don't worry about her, she's just another Gogglehead."
by Prashant October 16, 2006