"Wings" (stylized as "Wing$") is a song by American hip hop duo Macklemore & Ryan Lewis, released as the debut single from their first studio album The Heist. It features uncredited vocals from Hollis.

Macklemore explained the subject of the single as follows:

The music video, directed by Zia Mohajerjasbi, alludes to an autobiographical story line. It depicts its main character (Macklemore) and his experiences as a young boy infatuated with basketball and basketball paraphernalia, athletic shoes in particular, and what adverse effect it had on him as he grew up.

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.

Then the music video shows kids and youth practicing because they wish "to fly".

The following scenes display a grown-up man (Macklemore) instructing youth in an apparent awareness campaign meeting them in a hair salon or while traveling on a bus, talking to them through an open book what he thinks is essential and what is secondary, warning them of the consequences of consumerism, particularly regarding basketball sneakers.

The music video then shows a flashback of the young kid back in school wearing Seattle SuperSonics apparel. On his way back home all alone, he is followed by three juveniles eyeing him. Then there is a scene where the kid has been roughed up and his sneakers stolen as he walks home only with his socks on. Reaching home, he can barely take off his socks to wear a new clean pair. The choosing of the Sonics jersey is poignant to add further autobiographical aspect to the music video again showing that it is about Macklemore's own experiences and about a friend that he knew.

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Wikipedia