seth plum said:

Being cool is difficult to quantify. I suppose it might mean great players who seemed to think their footballing excellence was a surprising afterthought, they were almost more interested in doing something else. They would have a modest insouciance, an un-nurtured confidence, it would all look pretty easy and obvious to them, they could carry themselves with a relaxed knowledge of who they are, they were great entertainers because of all that, and because they had, dare I say it, a certain x-factor.
I am hoping others can change my list with obvious examples of those I have forgotten. I have not included Eddie Firmani or Alan Simonson because I think they were level above cool!

GK. Charlie Wright. Would chat to supporters behind the goal and accept the odd fag or two when offered.
RB. Terry Naylor. Would hold up his arms pretending to catch a high ball as it dropped, then control it brilliantly and off he would go. Worked every time.
LB. Chris Powell. At ease with everything until age caught up with him. Legend in all ways.
CB. Joe Gomez. A youngster who emerged looking like he had played for 1000 years.
CB. Jorge Costa. Never looked like a player, never looked like he would be beaten, never forgotten.
LM. Paolo di Canio. A Charlton vignette it was a joy to experience. Utter class.
RM. Colin Powell. No pace, no tricks, no defending, no aggression, but his crossing and ease was awesome. That thing when he waved his foot over the ball to leave defenders on their arses was wonderful. Won us a lot of pens with innocent magic.
CM. Claus Jensen. A player who could kill a ball stone dead, do what he wanted with it, whilst all the time looking like he would rather be lounging around with his headphones on listening to Dark Side of the Moon.
CM. Yoni Buyens. Stylish and the best (of many good ones) penalty taker I have ever seen in our shirt. Fantastic awareness.
ST. Lyle Taylor. Does this really need explaining? Combination of a kind of Renaissance Man, alpha male, great player and an impressively articulate guy.
ST. Yann Kermogant. Every free kick was more or less a penalty. A one off, a footballing genius for us who had looked into the depths as a young guy yet played with an abandon that was brilliant, always knowing that it is only a game.

Maybe not the best ever, but I would've paid double to watch that team.

Johann IceBerg Gudmundsson