1. “Swore I was gonna be someone, And growing up everyone always does.” from “Otherside”
This song, the first one he wrote after becoming sober, was arguably the first track to gain Macklemore some online buzz. It’s a tell all, intense story of addiction and the people it hurts. This line at the end always gives me shivers and really speaks to the fact that anyone can become an addict, but nobody expects to be one.
2. “I don’t control life but I control how I react to it” from “Vipassana”
This track is all about faith, Macklemore’s complex thoughts on the topic, and how it helped him get through his hardest times. This line helps sum up his thoughts, and explains that you have to pick your battles in life.
4. “So I stare into this paper instead of sitting at a cubicle. Take all ugly shit inside and try to make it beautiful” from “Vipassana”
A common theme in Macklemore’s music is the fact that he proudly chose his passion and love for music over a stable, dependable, cubicle job. His music is his valiant (and successful!) effort to turn his often ugly internal thoughts into beautiful music.
5. “A generation of kids choosing love over a desk” from “Ten Thousand Hours”
Again, Macklemore chose music over an office job. He thinks that more and more kids are doing that these days, resulting in a burgeoning, passionate music scene.
6. “They told me to just do it. I listened to what that swoosh said” from “Wings”
The most intense line from one of his most intense songs speaks to how huge corporations can capture young consumers and have large impacts on their lives, either positive or negative. Nike basketball shoes were his particular childhood obsession that led to an addiction to consumption.
8. “Thought it would be shiny and beautiful, Thought it would be alive and like musical, But it feels like someone died, it’s got the vibe of a funeral” from “Jimmy Iovine”
This track deals with his lack of a record deal and decision to be a completely independent artist. The song tracks Macklemore as he breaks into a label’s office to “steal” a record deal. Then, when finally offered one, he decides against it. This line describes the feeling of walking into the office, expecting an exciting vibrant culture, he sees the exact kind of office life he has spent his life trying to avoid.
9. “She said ‘We have a flame, your fire’s ignited with sound. Are you building the empire up, or using your fire to burn it down?’” from “Contradiction”
This song speaks to the contradictions in his music, his complex views on drugs and alcohol, sexism, and the like. After a run in with a fan who tells him that everyone has a little power (a flame) that they can either use to maintain the system of sexism, or help in bringing it down.
11. “I will moon walk to Pluto in honor of Michael Jackson. In heaven he’ll be saying that man is tight at dancing” from “And We Danced”
Macklemore has many sides. And while he has some great, extremely serious songs, his goofy side is pretty awesome too. This track was his original party anthem and praises the great dance king, MJ. It’s also one of the best set closers ever.
12. “But we still owe ‘em 40 acres, now we’ve stolen their 16 bars” from “White Privilege”
This song is gold. If you haven’t heard this side of Macklemore, I urge you to now. This track explains his thoughts on being a white rapper in a culture that was invented by African-Americans. This is possibly the best song to ever sum up this constant controversy.
13. “I learned from my teachers but became through my music” from “The Town”
Yeah, teachers can teach skills and valuable education, but Macklemore didn’t become who is in a classroom!
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