I'm kinda sleepy/hungover, but assuming that I can pick anytime...
IP's Sophistocated Holligans
Explorer: Neil Armstrong

A real American hero and explorer in every sense of the word, Armstong is a military vet and a freaking actual spaceman. On top of that, he's not above laughing at himself, and all money gained by his fame is donated to charity.
Monarch: Honest Abe
Author Ernest Hemingway
Wild Card: Bill The Butcher
Pro Wrestler: Hacksaw Jim Duggan
80's TV Character: Al Bundy
Philosopher: Tupac Shakur
TV Host/Announcer: Tommy Heinsohn
Comic Strip Character: Huey Freeman, The Boondocks
Celtic: Robert Parish
Explorer: Neil Armstrong