(3)Gordon Freeman vs (14)Tina Armstrong 2002

Tina Armstrong vs Gordon Freeman (2002 Characters)

Forget Master Hand. Forget L-Block. Forget Bidoof, Mudkip, CATS, whatever joke characters you want to throw up on the list. No match will ever be as funny as this one. This saw the birth of a legend and a repository of jokes for nigh unto five years of rich contest history: Gordon Freeman Never Wins. And when he loses, he always does so in a spectacularly embarrassing fashion, in a match he could easily have won, against an opponent he has no business losing to.

What makes this match so funny is that, unlike Max Payne, Sam Fisher, or Leon Kennedy (or Duke Nukem, for that matter), nobody cares about Tina Armstrong. She’s a D-list character in a C-list game series. As Amazing Telephone put it, all that’s pretty much ever been written about Tina Armstrong is her aspirations in life, her relationship with her cowboy father, and her measurements. And she beat Gordon Freeman. There is no mathematical solution for why this was possible – people have tried to figure it out over the years, and explanations have ranged from “nobody knows who Gordon Freeman is” to “Gordon Freeman is an avatar for the fat, nerdy gaming community – and we don’t like ourselves” to “LOL BOOBIES.” Regardless, this match will always take the cake as funniest damn match in contest history. You’ll always be a winner in my book, Gordy.