The music video starts with Macklemore now a grown-up man, going into an empty basketball court, where the indications are, that he apparently used to practice basketball himself. Macklemore raps while he reminisces himself as a small kid wearing a Chicago Bulls jersey number 23 (clearly alluding to NBA player Michael Jordan) and wearing, in a close-up, Nike sneakers that would "make him fly" (another reference to Nike Air Jordan sneakers). He describes "touching the net" as being the "best day of my life" (also a sample of a Jordan typical Nike ad), boasting about his skills to his mother and friends... until that is "my friend Carlos' brother got murdered for his fours, whoa", a reference to the basketball shoes he was wearing. This incident becomes a wake-up call to young Macklemore.
