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This gen probably just Monster Madness. That game was atrocious.

Of all time, it definitely has to be games for Nintendo consoles, because those things used to empty out bank accounts. Let's see...

$80 for brand new South Park for N64
$110 for near launch Star Wars: Shadows of the Empire for N64 from Funco Land in New York. I had an evil grin the day they got bought out just because of the feeling of getting ripped off so badly when I was younger.
$70 for Spawn for SNES



Tag: Became a freaking mod and a complete douche, coincidentally, at the same time.