This song finds Macklemore rapping about the influence held by multinational corporations like Nike, and the evils of advertising. He explained its meaning on his website: "The song 'Wing$' is about the pursuit of identity through the means of consumerism," said the Seattle rapper. "The attempt is to dissect our infatuation and attachment to logos, labels, brands and the fleeting happiness that is intrinsically linked to the almighty power of the purchase. The subject I use in the song is shoes, but its aim is to paint a broader picture of being a consumer and tracing the lineage back to my first memory of retail infused desire."
A heavily-edited new version song was used for commercials involving the 2013 NBA All-Star Game. The tune was used in TNT television channel's promotion for it and at the event itself. Some fans criticized Macklemore for allowing all negative references to Nike to be edited out, or taken out of context. Macklemore responded in a lengthy message to the criticism leveled against him of selling out by stating that lyrics have to get cut in order for the trailer/ad to make sense with what the company is promoting. The Seattle rapper added that if you take away the consumerism cautionary core of the song, a story still remains that he's still proud of, and he's happy that it's relatable enough for TNT to want to use it.
This started off as a two-person a cappella that Macklemore had written and performed. Seattle filmmaker Zia Mohajerjasbi, who has worked with many members of his city's hip-hop community, enlisted singer-songwriter Hollis, to convert it into a proper song so that he could then shoot the video for it. Hollis recalled to Billboard magazine: "There was no beat for the song, there was no song, but we all endeavored to make it, so over 8 months we did a Kickstarter and Ryan spent hundreds of hours on the song. It needed a chorus, and so I wrote the chorus for it and found some kids to sing it, and we recorded them singing it after school. It was such a holistic process, and it was an amazing way for us to bond as friends and as collaborators - it was very much all hands on deck."