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6. IVAN, PHOEBE AND "MAITREYA"
The X-Files, "First Person Shooter" (Season 7, Episode 13)
Wow. I'd forgotten this existed until I sat down to write this, but I'm informed it's remembered as one of "the silly ones" and "legendarily bad" by people who were way more into The X-Files than I was.
It's an episode about video games from a 90s genre-show, which means it's about a "virtual reality" game that drops players in lightly-decorated paintball armor into photorealistic B-movie scenarios that somehow starts killing its players for real. Of course, the players (apart from Mulder and Scully) are schlubby dorks. Of course, the developers (Ivan and Phoebe) are morally-problematic shut-ins who could end the killings by shutting down the game but won't because "My creation!!!" Of course, the "world's greatest gamer" brought in to fix things is a steely Asian guy who busts out the John Woo guns-akimbo routine. Of course.
The culprit, Maitreya (Krista Allen, so at least there's that), a sexy virtual-nemesis who's not even supposed to exist in the game... Twist! She's was created by Phoebe for a separate female-led game she was making to escape her testosterone-heavy work-life, but somehow jumped over to the "boy game" and is now killing male players to feed off the macho aggression Scully has been tut-tutting about the whole episode. Yup -- our actual premise is that a woman asserting herself in game development creates a (literal) man-eating monstress that kills guys and wrecks the game. Delightful.
5. LISA SIMPSON
The Simpsons, "Lisa Gets an 'A'" (Season 10, Episode 7) and "Gone Abie Gone" (Season 24, Episode 4)
The Simpsons could well be the most pop-culturally significant television series of all time, and Lisa might the show and its medium's crowning achievement in rendering complex, positive female characters. It's also been a consistently forward-thinking show on the subjects of technology and (frequently) games in particular, with almost everyone in the family having had video-gaming as a hobby at one point or another.
So it's unfortunate that both times games and Lisa have crossed paths, the story has (however amusingly) fallen back on the trope of video games as a quintessentially anti-intellectual exercise: In "Lisa Gets an 'A,'" she gets so addicted to a game of "Dingo Dash" (read: Crash Bandicoot) that she forgets to study and has to cheat on a test for the first time. In "Gone Abie Gone" she gets addicted to Internet Poker and loses her college savings (or so she thought).
::Comic Book Guy Voice:: "Hmph! Soooo! Video games get to be bonding experiences for dopes like Homer and Bart, and even Marge got to kick some ass in the MMO scene, but put a game in front of the smart character and it's all over for her, eh!?" ...or, y'know, it could just've been a funny story. That's also a possibility.
4. LITERALLY EVERYBODY
Code Monkeys (Series)
Yes, I know some sundry otherwise-decent members of the Nerd-God Periphery did some work here and there for this short-lived series, but still... was there ever a more schticky, bro-tastic pander-fest in regards to game-themed entertainment than Code Monkeys? And I mean setting aside the fact that it was seldom very funny and featured very little clever insight into the "gamer culture" it was trying to be the cartoon vanguard of.
Yes, fine, we're not necessarily supposed to "like" Dave and Jerry, but their frat-boy antics are clearly meant to be laughed along with instead of at and the complete lack of actual likable characters around them takes the "anti" out of their "antihero" designation pretty quickly.
But okay, fine, the Jonathan Coulton song is catchy.