@mrfluke A Japanese comedian, Shinya Arino, attempts to finish various video games or fulfill different challenges related to that game. There are also segments where he visits old arcades, talks about classic video game consoles, and other vg comedy bits they've tried over the years. The first show aired in 2003 and he's still at it!
Almost forgot, there's even a DS game based on the show, Retro Game Challenge.
Quite good, unfortunately the sequel never got localized.