There have been lots of actors who have played Bond. Sean Connery, Roger Moore, George Lazenby, Timothy Dalton, Pierce Brosnan and currently Daniel Craig. They have all been “cool” in their day and all reflected the times when the films were made. Roger Moore was a late 70s early 80s Bond and these were very different times to the Sixties and Nineties and today.
Today we are keen to look back and judge the coolness of the eras by today’s measurements and as a consequence Connery is perhaps judged the coolest of all Bonds. Skyfall though is the absolute box office smash, so perhaps Danieg Craig is challenging Connery for the title of the coolest Bond.
I think it is too soon to judge but it is fun being caught between the two!