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.