John Watson (Sherlock Holmes)
Rinoa Heartily (Final Fantasy 8)
Solid Snake (MGS series)
Gaius Baltar (Battlestar Galactica)
Oboro (Suikoden V)
A slime (Dragon Quest series)
Zuko (Avatar: The Last Airbender)
Athena Cykes (Phoenix Wright: Dual Destinies)
* Making instant oatmeal.
Pretty much just what it sounds like.
* Oregon Trail, real-life.
As in, actually spend 5 months hiking the 1842 West, but with the experience rigged to be strangely similar to the video game. Making it to Oregon > Giving up and settling in Colorado > Death, and tiebreaking if both make it is time taken with a 2 week penalty per family death. (So 2 kids dying of dysentery would lose to a deathless trip that took 3 extra weeks.)
* Reaching Enlightenment.
By default something akin to Buddhist Nirvana, but a lot of room for "interpretation" here.
Also, in unused ones from the PM I sent CK last time... (since Alien Hoax & Deal with mob of enraged Canadians were used... actually, was Jobbing used as well? I forget, but whatever, it's a good skill to have regardless.)
*Become Prime Minister of Canada.
(Whether by party elections, or coup + giving yourself the position, or alien mind control rays...)
*Toil in maple syrup mines
(You have been cruelly enslaved by evil Canadians to mine (???) maple syrup in the deep caverns of the frozen north. Who can get the most maple syrup out for the longest? Requires dedication of the mind and spirit as well as the body to not lose yourself and go crazy, and then fail to make quota.)
*High-powered business consulting
(Swoop in on a business at behest of management, figure out how to optimize synergies, reduce inefficiency, migrate the reports database, make some cool PowerPoint slides with pie charts, ask employees what they do Office Space style, etc.)
*Shoot the moon
(Up to the contestants what exactly this means, whether it be play a game of Hearts in a particular way, get in a spaceship and fire bullets at the moon, go for some out-of-reach girl, etc.)
*Jobbing
(The contestants must intentionally "lose" to a young up-and-comer in their field, but make the loss look good, as if it was all the upstart's skill that allowed this.)
*Fire Emblem Tactician
(Says it all, really, move your troops around a grid .)
*Ennui
(Contestants need to become bored, unhappy rich people who have everything they need, yet nothing substantial to do, and aren't content. Or at least unhappy hipsters who've seen all the good bands already, and it's all downhill from here.)
*Farming
(Be a farmer. Cows, hoes, manure, etc.)
*Frame Phoenix Wright for murder
(At least get him arrested , and ideally convicted, although the second part may be tricky.)
*Best hair
(As it says.)