Cool War

My brother proposed a video game in which you play as a mage who works a desk job to pay his mortgage. I added that the purpose of the game should be for the mage to purchase a video game so that they can play as a mage struggling to pay his mortgage within the game. He accused me of not knowing what's cool. What followed was a battle of images where I sought to use my knowledge of cool to attack his stronghold and push him off of cool hill. Little did I know that he was prepared to parry each attack. Who has won the battle of the cool (or are we all losers in this crazy thing called war)?

Round 1
My attack
His parry

Round 2
My attack
His parry

Round 3
My attack
His parry

Round 4
My attack
His parry

Round 5
My attack
His parry

So, who is the king of cool hill?