The 'Like A Boss' meme originally gained massive popularity through the 2009 Digital Short by The Lonely Island featuring Andy Samberg. While the song satirizes corporate life with increasingly absurd actions, the phrase quickly evolved into a visual meme, often depicted via Rage Comics characters or confident figures wearing sunglasses. It is used to illustrate doing something—regardless of how mundane or disastrous—with a sense of extreme confidence, swagger, or authority. Today, it remains a staple of internet culture for highlighting small victories and 'alpha' behavior in everyday situations.