Susunu! Denpa Shonen aired in Japan from 11/1/98 to 09/29/02 and was very popular. It became so controversial for the sadistic challenges it put its contestants through that the show was cancelled when the Japanese governement cracked down on "torture"-themed shows. Keep this in mind when you start to think "this can't be real". This stuff actually happened.
Hulu.com is now offering two of the show's challenges with English subtitles (click the "cc" box). A third challenge has a couple episodes but doesn't reach completion. Both of the shows I'm linking to get to the finale.
Nasubi, episode 1 (of 8)
Nasubi, like most of the contestants, was an unknown comedian looking to get famous. After winning a place on the show by random draw, he was immediately blindfolded and brought to an apartment to start his challenge.
Nasubi's assignment was to live entirely off of sweepstakes contests. He was given an apartment with a toilet, shower, air conditioner, kitchen with single stovetop, phone, table, cushion, pen, blank postcards, and a large rack filled with current magazines. Nasubi wasn't permitted to have anything else, including food or the clothes he wore into the apartment.
Nasubi had to enter sweepstakes contests for food, clothing, or anything else he wanted. Otherwise, he'd go hungry, stay naked, and be without life's necessities.
Nasubi would win the challenge when he won 1,000,000 yen in prizes.
Funako, episode 1 (of 6)
Funako Tsubaki's challenge is to save as much money as possible in preparing dinner for a family of four. Each morning she randomly draws a dinner. She then checks a large # of flyers to find the best bargains on the needed ingredients (usually four items need to be bought).
Of course, there's quite a catch. Funako has to search flyers from the entire Kanto region in Japan. The Kanto region includes Tokyo and is over 42,000 square kilometers in size. Since she is trying to save money, she obviously can't drive to these places to save just a few yen per item. She has to bicycle everywhere she goes in this massive region.
If she succedes in buying all her items on a given day, she can make dinner and eat. If she fails, she doesn't get to eat that day.
Funako will win the challenge when she has saved enough to go to Disneyland.
The episodes can get easily get redundant as we watch the contestants do the same thing day after day. However, surprises and hilarity are usually not too far away. In particular, both of these challenges have great endings (so don't look anything up and spoil it for youself).