I am not sure whether Bubba Gumps and Planet Hollywood would fall into the 'cool' category. Going to a bar in Times Square is like drinking in Leicester Square.
I have been to the revolving bar in the Marriott, and it was free before 19:00, and if you wanted to stay there afterwards you had to pay. There is also an office block next door which is taller and ruins about a third of the view.
Have a look at this website if you want some suggestions on cool bars:-
http://www.worldsbestbars.com/city/new-york
I have been recommend the Campbell Apartment a couple of times, I think that you need to be smart to get in. It is in the old office of John Campbell in Grand Central Station:-
http://www.worldsbestbars.com/city/new-york/ca mpbell-apartment-new-york.htm
I have also had a bar called 7B recommended a few times
http://search.cityguide.aol.com/newyork/bars/7 b/v-106900088