[octothorp]

Some interesting thoughts here.

My concern with humourist/comedian is that it's pretty specific to modern history. Most of the categories, you could find a good candidate from any century in the last 2000 years or more. With humourist, I think pretty much every selection would be 1800 or later. Yeah, there are a few writers you could point to from earlier periods, but in most cases they would be thought of as a writer or philosopher who used humour, as opposed to a humourist/comedian. Isn't a comedian simply a kind of writer who performs the work that he writes?

That said, I think Itse's point about military interpretations of history is valid. Perhaps this draft is a good candidate for using the same system we used in the lit draft, where you can trade categories, and stock up on the areas you think are important. Perhaps start with a breakdown of 1/4 military, 1/4 political/civil, 1/4 arts, 1/4 knowledge and invention. And maybe a couple wild-card categories like women (though I suggest that in reverence to Bill and Ted, they be called Babes).

Here's some revised suggestions, trying to take into account as many things as people have said in this thread as possible. I've tried to limit it to 20 categories:

Military:
Military Leader: can be a purely military leader, like a general, or a military/civil leader, like a warlord
Soldier: Can be from any rank, but someone who is recognized for what they did on the field of battle, rather than tactics
Vigilante/Outlaw/Rebel: Someone who challenged authority either as a leader or as an individual, and either for personal gain or out of principle
Military Wildcard

Political/Civil
Political Leader: Can be elected or non-elected, and at any level (municipal, regional, national, imperial).
Innovator: Someone who shaped history through their ideas about how societies and civilizations should operate. Could be another leader, could also be a civil planner, a judge, a lawyer, an architect, etc.
Humanitarian: Someone who helped civilization through politics, policies, or direct actions; could be used to pick someone in the medical community, for example
Political/Civil wildcard

Arts:
Writer: including playwright, poet, novelist, essayist, and storytellers; does not need to actually write, such as any word-based performer performing his/her own work.
Visual artist: painting, sculpture, tapestry, etc.; any form of art that is primarily appreciated through sight.
Composer/Musician: Can include either people who wrote music, or those who performed music written by themselves or others.
Artist Wildcard: any of the above, but can also include other mediums, such as acting

Knowledge / Ideas:
Inventor / Scientist: Someone who contributed to human knowledge and understanding either through theoretical science or through invention.
Explorer / Discoverer: Someone who contributed to human knowledge through discovery of the world around us, primarily through observation rather than deduction. So not only could you have someone who explored, you could also choose someone who cataloged species or rock formations.
Thinker / Philosopher: Someone who established a body of thought concerning the classic problems of philosophy, or other ideas.
Knowledge wildcard:

Additional Wildcards:
Women (Babes)
Eastern: any historical figure from 'eastern' cultures, including ottoman empire, persian empire, and east.
Southern Hemisphere: African, South American, Latin American, or Australian political figures
Living: Choose one living character who you think will be remembered as being historically important after they've died.