Lol...lol...
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Good question... In no specific order
Carlos Fuente Sr (I mean if you are going to have a cigar, the cigar knowledge he could share during said cigar would be awesome)
Mel Brooks
Julius Caesar (the Roman not J.C. Newman)
Runners up, Thomas Jefferson/Ben Franklin, Simon Bolivar (incredible life's story), Winston Churchill, Albert Einstein, Galileo, Charles Maurice de Talleyrand, Dave Grohl and Mike Ditka.
Since I like to cut up like a show dog, I'll go with the Three Stooges......
W C Fields
Monica Lewinski
JFK