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In my middle-school world of Little League softball and sleepovers, I found myself listening to Macklemore’s (and Ryan Lewis’s) discussion of addiction, greed and failure throughout the album “The Heist.” Tuning out my parents’ car ride conversations and team chatter on the bus rides to basketball games, I let my headphones become the vessel into Macklemore’s much darker musings about critical issues I had not yet realized or experienced. 

No one in my social circle was openly gay until I got to high school, but “Same Love” introduced me to and harnessed my empathy and support for same-sex marriage, an issue I had no connection to at the time. I learned what “lean” meant after listening to “Otherside” and googling the abuse of cough syrup. Prior to hearing “Thrift Shop,” Goodwill was only a place to donate clothes, not to buy them. Before I experienced “Wing$,” I never contemplated why I preferred Nike over Under Armour. Human rights, substance abuse and consumption contribute to the central themes of the album. At the time that I first encountered “The Heist” as a relatively sheltered middle schooler, I hadn’t devoted a lot of time to thinking about those things. Nevertheless, I found myself feeling a deep emotional connection to Macklemore’s philosophy of fighting for gay rights and battling inner demons throughout “The Heist”, a bizzare connection I could not explain with my middle-school mind.

Since stumbling upon his Grammy award-winning album, I have become much more familiar with Macklemore and his music, from the nostalgic tones of “Growing Up” and “Good Old Days” to the more bizarre sentiments of “Brad Pitt’s Cousin” and “How to Play the Flute.” I have taken on the shared philosophical weight of “This Unruly Mess I’ve Made” and observed his anecdotal reflections on childhood and religion in “Gemini”.

At the end of 2020, I found Macklemore’s first full-length album, “The Language of My World,” which covers, among many other topics, his childhood observations of socioeconomic strata, his first experiences with alcohol and illicit substances, and the track “White Privilege” (which would be followed by the better-known “White Privilege II” on a later album). The 2005 album’s discussion of social issues still present and exacerbated by the pandemic made “The Language of My World” seem like it could have been penned in 2020. “The Language of My World” fleshes out Macklemore’s personal reflections of growing up in a segregated Seattle as a well-off white kid. It provides compelling social commentaries, all of which seem to be perplexingly embodied by the track “Contradictions,” which boasts the hook: 

“Consumption, contradiction/

I’m conflicted with being a hypocrite/

And through these songs you can witness it/

The differences, I admit this shit, because I’m just like you/

Walking a fine line between saying and living it”

Since my initial middle-school musings on Macklemore’s more palatable (or at least, commercially successful) tracks, I have been able to identify the potential contradictions of his career and artistry.

After all, Macklemore is an A-list celebrity critiquing those who buy into and practice conspicuous consumption in songs like “Thrift Shop” and “Need to Know.” Conscious consumption is somewhat of an unusual position to advocate for in popular music, and bringing it up seems like an admirable undertaking. However, he romanticizes overbuying and rocking used clothing without a mention of gentrification in “Thrift Shop.”

Considering the bigger picture, Macklemore attacks conspicuous consumption in his signature song, exclaiming “Fifty dollars for a T-shirt/ that’s just some ignorant bitch/ I call that getting swindled and pimped.” Explicitly mentioning the entrapments of buying Gucci, he cautions “Trying to get girls from a brand?/ Then you hella won’t.” By his own definition, Macklemore’s been swindled by the same systems and propaganda he so famously preached against. Instagram posts and interviews reveal his adornment of Gucci and expensive accessories like Louis Vuitton duffle bags and Rolex watches. Even if the Gucci hats and shirts are fake, as he has claimed, it is a blatant violation of the ideology propagated in one of his biggest hits.

Though he preaches from a perspective of conscious consumption in “Thrift Shop,” he also admits numerous ways in which he has failed this ideal, including his being seduced by his lifelong, very American dream of buying a Cadillac in “White Walls.” Macklemore describes the sentiments attached to the purchase: I’m rollin’ in that same whip that my granddad had/ Hello, haters, damn y’all mad/ 30k on the Caddy, now how backpack rap is that?”

Taking a more contentious tone towards our economic system, Macklemore dedicates an entire song, “Wing$,” to chronicling his lifelong struggle between having a love for sneakers and addressing the relationship of such a passion with conspicuous consumption, socioeconomic inequality and shallowness. In the song, Macklemore looks in the mirror, challenging himself: “Will I stand for change or stay in my box?/ These Nikes help me define me/ But I’m trying to take mine off.” Macklemore concludes that he has learned “For a hundred dollars and some change/ Consumption is in the veins/ And now I see it’s just another pair of shoes.” 

Since the release of “Wing$,” Macklemore has collaborated with Jordan to produce three pairs of shoes, making extremely low quantities of each. Macklemore also has an extensive sneaker collection. In an interview with GQ exposing his failed attempt to take off the shoes, he discusses his collection and prices his rarest pair — Jordans which he helped develop — at $25,000. Macklemore not only has several pairs of shoes worth hundreds, if not thousands, of dollars, but has developed multiple pairs of shoes that are outrageously priced, rare and unattainable. Detailing his development of the Air Jordan 6 ‘Emerald City’ in the same interview, he admits that “exclusivity … is what drives the sneaker market (and) is what we all buy into.” Mentioning how the sneaker market feeds into consumerism and capitalism in another interview, Macklemore reflects, “There’s things that inherently bother me about the culture that I also love.” Despite a whole lot of reflection and work into producing an entire song in which he acknowledges “We are what we wear/ We wear what we are,” Macklemore’s hypocrisy with regards to the consumption of shoes is perhaps the most straightforward example of his contradictions.

However, Macklemore’s release of his own golf apparel brand, Bogey Boys, gives the hypocrisy of Macklemore’s shoe collection a run for its hundreds-of-thousands-of-dollars price tag. Remember the statement about $50 T-shirts? Bogey Boys’s T-shirts start at $38 — $12 more, and the lyrics of “Thrift Shop” may have become as broken a record as “Wing$” is in light of Macklemore’s GQ interview. According to his own doctrine, he is a washed-up millionaire, an underground rapper turned mainstream celebrity, whose hit song cements his hypocrisy — alas, this is a recurring conclusion when exploring his many contradictions. 

Macklemore demonizes the music industry that is partly responsible for his wealth and fame as a somewhat-independent musician with record-breaking commercial success.  Macklemore affords a great deal of criticism to the music machine in his and Lewis’s independently produced tracks. “Jimmy Iovine,” named after a mogul in the industry, recounts a fictional encounter with Iovine in which Macklemore rejects his record deal offer, proclaiming he’d “Rather be a starving artist/ Than succeed at getting fucked.”

“Light Tunnels,” which opens his 2016 album “This Unruly Mess I’ve Made”, follows Macklemore through his attendance at the 2014 Grammys, during which he won 3 awards, including Best Rap Album and Best New Artist. Describing the sea of gold and Botox surrounding him at the ceremony, he reveals, “This feels so narcissistic, dressed as a celebration to conceal it’s a business” and contemplates his inner conflict of knowing “I got the people’s attention, don’t wanna lose it here/… But wanna make sure I’m invited next year.” The music industry deserves the criticism that Macklemore and Ryan Lewis fashion into goosebump-ensuing poetry without the typical industry aid offered to music that reaches the mainstream waves. 

However, the same industries and structures that Macklemore critiques have inevitably aided him in becoming an A-list celebrity that wears Gucci, owns shoes that cost more than a year of in-state tuition at the University of Michigan, and enjoys a lifestyle that, to Macklemore, is worth sacrificing his dignity for. But what is Macklemore supposed to do? Not let his songs play on the radio? Boycott the Grammys as an icon of the independent music movement? Considering the alternatives makes Macklemore’s decisions no less contradictory, but if the greatest goal is for the music to reach as many people as possible, the industry only aids in that endeavor.

Since “Contradictions” was released on his 2005 album, no songs have captured the gravity of Macklemore’s contradictions as much as “White Privilege” and “White Privilege II.” Though his celebrity status and consumption leaves much to be desired of the “Thrift Shop” star, Macklemore’s existence as a white rapper seems to be the contradiction that invites the most criticism of his music, even from the artist himself. In “White Privilege II,” he contemplates, “You’ve exploited and stolen the music, the moment/…Your brand of hip-hop, it’s so fascist and backwards.” As such, he ponders the authenticity of his art with regards to the history of hip-hop and cultural appropriation, begging questions of whether he has a right to be a hip-hop artist, and how legitimate his music is when it is built from a genre white people did not create, but have profited immensely from.

He questions his place in political discourse and hip-hop as a white man and a white rapper, but articulates his perspective in every song that offers a social commentary. He revisits these questions and his sentiments of self-awareness in the two tracks, criss-crossing between conclusions that leave his right to rap null and void, and inspiration to use his platform to push for social equality.

In “White Privilege” he admits “Hip-hop started off on a block that I’ve never been to/ To counteract a struggle that I’ve never even been through,” concluding over a decade later in “White Privilege II” that “If I’m only in this for my own self-interest, not the culture that gave me a voice to begin with/ Then this isn’t authentic, it is just a gimmick.”

It is worth asking whether Macklemore, as a white rapper, can be an advocate for the social causes that birthed hip-hop. Even if he is unique as a white rapper in the music industry by explicitly supporting all the right causes at the right time, he concedes “I give everything I have when I write a rhyme/ But that doesn’t change the fact that this culture’s not mine.” As a white girl who listens to much more classic rock than hip-hop, I do not claim to know what qualifies an artist as legitimate or authentic in producing their art. The concepts of genre and originality when it comes to art are stifling to me, and I do not know if I will ever be able to answer whether Macklemore ought to continue pushing for social equality through his music, or push away the pen, make a public apology and donate all his profits to those living through the circumstances that inspire hip-hop.

To me, Macklemore represents, embodies and philosophizes on the concept and reach of contradictions; his music encourages and leads me to question the ever-present hypocrisy in many things, especially in my own life — in every decision I make, every song I listen to and every dollar I spend — each and every day. Maybe my spending my time on the music, Instagram posts and interviews of a celebrity, when I know they contradict themselves to a great extent, is a contradiction on my own. Maybe my being inspired to believe in and fight for a more equal world by music made by a celebrity, when I question whether celebrity is a contradiction to social equality is a bold, troubling contradiction. Maybe writing an article, thus drawing attention to art that I cannot say that I unconditionally endorse given such contradictions, is the most questionable contradiction of all. Hell, there’s bound to be countless contradictions throughout these paragraphs. 

But if I decided to avoid all music that fails to exist in complete alignment with the principles it preaches, I’d be left with a lot less music (and art) to listen to and learn from. We live in a society where a lot of music is produced, in part, for profit, by millionaire executives and musicians in an exploitative industry in which art is often, and perhaps inevitably, commodified. Regardless, this line of thinking undermines our ability to think critically and take away what we ought to from art. Macklemore’s music has aided me in many ways, especially in becoming more sympathetic to the political struggles of those unfamiliar to me, while internalizing that “‘Everything’s peace and love?’/ That’s somewhat misleading/ Because this world is fucked up and I’m a product to what I’m seeing.” 

Macklemore’s catalog offers much more than just questions about the essence and reach of contradictions, most notably feelings of childhood nostalgia and sympathy for overcoming personal failures. Whether condemning Big Pharma and reflecting on his battles with drug abuse, denouncing the presidencies of George Bush and Donald Trump, reliving his early, sacred memories of adolescence or pondering greater questions about the existence and impacts of art, Macklemore weaves webs of incredible rhymes that roll off his tongue into and around my mind. He philosophizes on art as his faith and therapy, as the vessel through which he fulfills his self-determined purpose on this earth. Macklemore has created tracks through which I can feel the nostalgia of my younger years, the strangulation of self-doubt and setbacks coupled with the strength and courage to overcome it all, and the wonder of all the questions that come with being a human being.

Looking back at how much I admired Macklemore in my middle school days, when I did not think as critically and knew much less, I have to admit I am disappointed when I see him wearing a Gucci hat and Google his net worth. But at the end of the day, with Macklemore’s embodiment of the principle and practice of contradictions as a real, flawed human being, I do not believe the world is better off without his art, and I owe much of my reflection about youth, passion, art and contradictions to his albums. Contradictions, to some extent, are an inevitable part of the human experience, and Macklemore’s willingness to embody hypocrisy and contradiction is his greatest contribution as an artist — an artist whose art allows us to identify and reflect on our contradictions in pursuit of actualizing a better world.Since his first full-length album and my first listening to “The Heist”, both Macklemore’s and my worlds have changed dramatically. I am no longer a middle schooler with little knowledge of the depth of America’s socioeconomic strife, and he is no longer an underground rapper. I am not sure how much I ever had in common, at least on the surface, with a troubled addict from Seattle, but his eloquent poetry articulating the unruly messes we all make has maintained the same connection from when I stumbled upon The Heist. Considering the endless questions of consumption and contradiction, I am conflicted with being a hypocrite. But through Macklemore’s songs I find inspiration — in his relatability as a conflicted, hypocritical human being; in his raw vulnerability to show such hypocrisy; in his courage to be so openly flawed, to himself and to the world; and in his attempt to inspire others as we all try to walk the fine lines between feeling, thinking, saying and living it.

Statement Correspondent Leah Leszcynski can be reached at lmleszcz@umich.edu.