The Coolest American Man of the Last 100 Years

Over the past several days, I have engaged in an extensive email colloquy with the Brothers Weeser* (minus Tim, to his detriment) sparked by a drunken question asked by Greg that merits discussion and deliberation:  Who is the "Coolest American Man, last hundred years? (Post Teddy Roosevelt?)"  Coincidentally, the 100th anniversary of Teddy Roosevelt's death is only about a month away, on January 6.  Teddy was a total badass.  Hell, he once got shot in the chest before a campaign speech, and he shrugged it off and made the speech anyway with blood soaking through his shirt.

But who's the coolest American man since then?  That, my dear readers, is the question we will need your help to answer.

How do you even define "cool"?
"Coolness" is hard to define, but like Justice Potter Stewart said about obscenity, you know it when you see it.  "Cool" suggests timelessness and influence, with some combination of debonair, ruggedness, and/or badassery mixed in.  To paraphrase one of the Austin Powers movies, it's someone who men want to be and women want to be with.  And just because someone is famous or good at what he does doesn't mean he's cool.  For example, Babe Ruth is a legend, but I don't know if I'd call him "cool."

How is this going to work?
What we're going to do is compile a list of candidates.  Then the Brothers Weeser* (minus Tim, to his further detriment) and I will seed them into a bracket.  We are going to be having two separate brackets:  one for dead guys and one for living guys.  Each bracket will have 32 men, and each will be divided into four sub-brackets of 8 dudes each:  (1) Athletes; (2) Hollywood; (3) Musicians; and (4) Other.  And then you will vote on them to determine the Coolest American Man of the Last 100 Years.

What are the rules?
Here are the rules:

1.  The guy must have been an American at birth, so either born in the U.S.A. or born abroad to at least one American parent (and if the latter, raised in the U.S.).

2.  The guy must have reached his "coolness" in the last 100 years.  It's safe to assume that, with limited exceptions, he will have been born on or after January 1, 1900.

3.  No politicians (as their primary gigs), so that this doesn't devolve into a political argument.

What's the schedule, man?
Voting will take place here on GMYH starting on January 6 -- the 100th anniversary of Teddy's demise.  We'll do a round (in both the living and the dead brackets) over the course of two days.  Tentatively, here is the schedule for voting:
January 6-8:  Round of 32
January 9-11:  Sweet 16
January 12-14:  Elite 8
January 15-17:  Semifinals
January 18-20:  Finals 
January 21-23:  Living champ vs. Dead champ

How do I help?
So here's where you come in.  We'll be taking suggestions over the next few weeks on who we should include.  Of course, we have thought of a bunch of names, but there are surely many who we haven't thought of.  You can comment on this post, send me an email at gmyhblog@yahoo.com, tell me in person, get a sky writer -- whatever it takes.  The question is:  who is the coolest American man of the last 100 years?