The 'I'm Playing Both Sides' meme originates from the Season 10 episode of 'It's Always Sunny in Philadelphia' titled 'The Gang Spies Like U.S.' In the scene, Mac (played by Rob McElhenney) attempts to explain his strategy of working with two opposing groups by blatantly stating his plan to their faces while wearing 'incognito' sunglasses. The humor stems from his utter lack of subtlety and the fact that he reveals his ulterior motive immediately. Online, the template is widely used to mock people who try to remain neutral or profit from both sides of a conflict, only to end up looking foolish. It has become a staple for political commentary, sports rivalries, and everyday social awkwardness.