Who is the coolest?
Coolness is a very subjective personal attribute. Everyone has a different measure way to measure cool, so this category will strictly be broken down by the age old standard: “Would you like to sit down and have a drink with this person?”
Obviously all of the Avengers would have amazing stories to tell, but imagine life outside of the Avengers. Bruce Banner might be a cool guy, but I don’t think he would be the best conversational partner. In this case, it seems Captain America or Iron Man would be prime options.
Captain America is a thoroughly fascinating person. He helped defeat the Nazis in World War II, he volunteered for a secret government experiment that made him Captain America, and he genuinely seems like an all-around nice person. You could just sit down and talk about the WWII days with him for a while, and then transition to how he has been adjusting to life in the 21st century after being frozen for so long.
Tony Stark, on the other hand, is an incredibly intelligent person with a larger-than-life personality. He likes to have fun with everything he does, and after the opening events of Iron Man 1, he really does have a heart of gold. It would likely be enlightening to talk to him about science and his inventions, see what his vision of the future is and how he plans to continue to help humanity improve. Even though most of this talk might fly right over my head, it would be incredibly fascinating, similar to having a talk about astrophysics with Neil DeGrasse Tyson.
As for who is cooler… personally, I would have to go with Cap. Tony has a ton of awesome gadgets and worlds of knowledge I will never share, but he also has a huge ego, and doesn’t seem to make friends easily. Cap seems like a guy who you can hang out with on a regular basis and always have a good time. He is perfect best friend material.
