What's your list?
COOL (Not worried about what people think, tough, plain- spoken, and/or NOT pc):
Robert Mitchum
Steve McQueen
"Papa" Hemingway
Sinatra
Dino (Dean Martin)
Muhammad Ali (boxer not prophet)
Robert Deniro
Miles Davis
Charles Bronson
John Wayne
Warren Oates
William Holden
Robert Ryan
Sam Peckingpah
Joe Pesci
Denzel Washington
Mel Gibson
Charlie Toraño
Jon (CAO)
Avo
Al@Perdomo (the fat bastid)
Redd Fox
Richard Pryor
Lee Marvin
Joe Gibbs (coach of the Skins)
3 Stooges (Moe, Larry, & Curly)
Andy Kaufman
Chris Farley
UNCOOL(tries too hard, mixed-up, contrived, phoney, nerdy and/or very pc):
Hugh Heffner
Ann Heche & Ellen DeGeneres
Andrew Dice Clay
Mike Tyson
ANY of the network anchormen
"Fonzie" (and Potsy)
"Bueller"
Any rapper with "Ice" in their name
Kennedy (pick 'em)
Tom "Mr. Scientology" Cruise
Joe Piscopo
Most Hollywood actors
"Mr. Johnny" Cochran & OJ
Shemp & any of the replacement Curlies
Lawyers
Politicians
Most corporate wonks
Morton Downey Jr.
Al Sharpton
Jesse Jackson
Kweisi Mfume (aka Frizzell "Pee Wee" Gray)
T.O.
Bill Gates
Bruce Springsteen
Michael "Crybaby" Jordan
Dan Snyder (owner of the Skins)
Any of the recent cast of SNL
Chevy Chase
You get the idea.