A decade later, what was the deal with Macklemore?

On The Heist, Lin-Manuel Miranda, and the 10th anniversary of the whole Grammys thing

Almost exactly a decade ago, Ben Haggerty did something pretty dumb.

Sunday January 26, 2014 started out as a monumental celebration for Haggerty, who spent the evening at the 56th Grammy Awards being celebrated from his work as the rapper Macklemore and his 2012 album The Heist with the producer Ryan Lewis. The pair won four awards and performed their marriage equality hit “Same Love” while Queen Latifah officiated several concurrent weddings. On the whole, it was a remarkable moment for a musician who half-a-decade earlier was known only to small pockets of Pacific Northwest backpack rap enthusiasts.

But then Macklemore sent a text. And then he screenshotted that text, and posted that screenshot on Instagram.

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The text, an apology to Kendrick Lamar after The Heist won Rap Album of the Year over the Los Angeles rapper’s masterpiece good kid, m.A.A.d city became instantly infamous. It was corny and more than a little bit disingenuous — if Macklemore believed deep in his bones that the award was a cosmic injustice, he could have simply not accepted. It’s the most notable, and perhaps most cringe-inducing, entry into the ever-growing canon of white artists publicly apologizing to more deserving Black contemporaries for winning a Grammy.¹

A decade later, the truly strange thing about the phenomenon that was The Heist is that Macklemore has largely disappeared from mainstream pop culture. If you catch a reference to Macklemore in the wild, it’s more than likely someone on Twitter² wishing a happy Pride to his uncle, or maybe “Can’t Hold Us” playing in, like, a Peloton class or something.³ More notably, there are vanishingly few artists that even sound like Macklemore. Maybe the most Macklemore-core rap hit since 2014 is the Wiz Khalifa Fast and Furious song, which is now eight years old.

Macklemore was an underground rapper from Seattle. Then he was one of the biggest pop stars in the world. Then he was a punchline. And now, 10 years later, he is something else entirely.

The Grammys are bad at rap and also weird

Because of the Instagram apology — and also because good kid is a towering monument of songwriting, performance, and storytelling while The Heist is merely a pretty good rap album — the Rap Album award has always been the main subject of controversy.

But the thing that made the 2014 Grammys particularly disappointing was that Macklemore & Ryan Lewis won not only Rap Album, but also Rap Song and Rap Performance — fully 75 percent of all rap awards given out at the 56th Grammy Awards. Half of all rap awards presented on the night went to “Thrift Shop,” a song that is not without its charms, but also come on now. It’s a jokey house party tune that prominently features a poorly aged R. Kelly punchline.⁴

The specific frustrations with the snowballing Macklemore momentum, eventually compounded by the decision to post those texts on Instagram meant that as time went out The Heist was burdened with the weight of decades of Grammy rap blunders.⁵

This is true across genres, but the Recording Academy has a particularly tortured history of attempting to recognize rap and hip-hop as art forms. Ask Pusha T about Will Smith and Jay-Z. For nearly two decades, the Recording Academy’s approach to awarding Rap Album was more or less “whatever Eminem put out this year.”

Macklemore’s wins within the rap awards made people so angry because they distilled the long-held frustration throughout the decades that hip-hop was becoming a singular cultural force: The Grammy Awards are very bad at understanding and celebrating rap. Notably, much of this badness manifests in a way that looks a lot like racism — rewarding white performers who are somewhere between mediocre and pretty good while ignoring the genre’s Black innovators.

Partially through his own decision to call attention to it, Macklemore made The Heist debacle a shorthand for decades of racist awards decisions. He also wasn’t helped by the Grammys’ strained relationship with the concept of time. Presumably to give everyone time to listen to everything, Grammy eligibility windows are shifted from simply a calendar year to a weird 12-month period that excludes the final quarter. In 2014, this meant that the awards were for albums released between October 1, 2012 and September 30, 2013.

This is confusing and silly in normal years, often leading to a very-belated celebration of music that has been out in the world for over 18 months. But it was even more so in the case of Macklemore.

The Heist was an album that came very slowly, and then all at once.“Thrift Shop,” the song that propelled Macklemore to breakthrough superstar status rather than simply rising rap star status, was released in August 2012. But it was also the fourth single from The Heist. It’s easy to forget the chronology, but “Same Love” was a hit before any of us had even heard the dread saxophone loop. The first two singles from The Heist — “Wing$” and “Can’t Hold Us” — were released in early 2011.

All of this adds up: Four of the album’s 15 tracks had been out for at least 17 months by the time the 2014 Grammys rolled around. Two of them had been out for three years!⁶

So The Heist was not only not the best choice for Rap Album of the Year, but by the time that it received the award it felt kind of old. “Thrift Shop” in particular had long since passed from funny YouTube video to genuine chart success to inescapable and tedious radio megahit.

Due to the history and particularities of the Grammys as an institution, the Macklemore dominance felt not only like the embodiment of decades of inane Grammys decisions, it also felt like a celebration of music that was already stale.

And then, of course, he made it worse.

The Heist is fine, and Macklemore is Macklemore

Separating the art from the artist is an often pointless task, but it is particularly impossible to separate Macklemore the rapper from Macklemore the person who made a weird Instagram that got people mad at him.

Because if there was ever an artist who would make the bizarre, simultaneously self-effacing and self-congratulatory decision of publicly apologizing for winning a Grammy, it is Macklemore: He is introspective to a fault, painfully aware of his position as a white interloper in a historically Black genre, and often incredibly corny.⁷

These are all attributes that lead a person to feel compelled to publicly apologize to Kendrick Lamar. They are attributes that sometimes lead a person to write arresting and emotionally compelling songs.

Macklemore ground his way through years of slinging CDs outside small clubs in Seattle, so by the time he got to record a big studio album he was obviously proficient at rapping. This is more or less the thesis of The Heist’s opening track “Ten Thousand Hours,” in which he celebrates the hardening experience of the come up.⁸ He can string together syllables in interesting flows, navigate complex rhyme structures, and often throw in a fairly clever bar or two. And he found a perfect match for his occasionally theatrical and always earnest raps in the form of Lewis’s backpack-rap-by-way-of-early-Coldplay instrumentals.

Macklemore is at his best when he successfully locates the midpoint between the cloying and the playful. With Lewis’s help, he is on that sweet spot more often than not on The Heist, nowhere more so than on “White Walls” which has an infectious joy that captures what it must have felt like to be Macklemore in early 2012 — playing with house money, pulling up to buy a Cadillac after years of pushing broken down cars around the Northwest.⁹

Meanwhile, songs like “Starting Over,” “Thin Line,” and “Neon Cathedral” are thoughtful and genuinely affecting, and it’s hard to argue with the big hits, non “Thrift Shop” division: The clap-along hook to “Can’t Hold Us” is practically weaponized to get stuck in your head; “Same Love” is lead-footed and clumsy but genuine and Macklemore has the good sense to let the sampled chorus from Mary Lambert shine.

The problems start when you try to compare Macklemore to other rappers. Because as much as he is an acolyte of any number of underground rappers of the 1990s and 2000s, he makes his own brand of theater-kid rap that feels somewhat divorced from what is usually great and compelling about the genre.

Macklemore songs are showy and tryhard in a way that a lot of rap songs are not. They’re also about effort in a way that feels clunky compared to most rap music. Rap songs about grinding? Sure. Rap songs about hustling? Absolutely. Rap songs about trying your best? Not as much.

And if nothing else, most Macklemore songs are about trying your best. The Heist finds Macklemore trying his best to preserve a deteriorating relationship (“Thin Line”), to manage ongoing addictions after gaining fame for getting clean (“Starting Over”), to reconcile violent consumerism with his love of sneakers (“Wing$”), and of course, to buy cool clothes on a budget.

These songs are earnest and emotional. They are also occasionally cringe-inducing, and sometimes cloying. They are songs, in short, written by the kind of guy who might post an apologetic Instagram after winning a Grammy.

One reason that Macklemore songs so out-of-place in the larger rap ecosystem is that there are vanishingly few artists making music that mimics his tone or sound. With the massive commercial and critical success of The Heist, you would expect a major label rush on overly earnest white rappers in the following years, but that simply didn’t happen. Mac Miller maybe had more in common with Macklemore than those of us who are fans of the late Pittsburgh rapper would like to admit, but his dedication to being hip-hop’s convener of new artists and aesthetics puts him in a firmly different lane. Jack Harlow is currently one of the biggest rappers in the world, but his appeal is all of Macklemore’s study of rap history with none of the pained acknowledgement of white guilt. The world is strangely short of Macklemore impersonators.

Part of this is Macklemore’s own doing: He was clearly uncomfortable enough with the level of fame that he achieved as a white rapper that he actively undercut it at times. The text to Kendrick Lamar was performative, but Macklemore is an artist who is genuinely interested in engaging with American racism: His 2005 debut album features a song called “White Privilege,” and on The Heist’s “A Wake” he spends the second verse rapping about how he is perceived as a white rapper and the obligation he feels to speak on social justice issues. In 2016, he followed up The Heist with “White Privilege II,” a 7-minute song about attending a Black Lives Matter protest, which has all of the signature Macklemore clumsiness but also was so far ahead of the brief moment of broad support for Black Lives Matter in 2020 that it might even be admirable.

A significant reason why we don’t have a world full of people trying to rip off The Heist is that Macklemore himself was deeply unitnterested in trying to follow up “Thrift Shop” with further “Thrift Shops.” For better or for worse, Macklemore was always going to try to tackle serious issues, and the more he picked thornier issues to rap about the more he guaranteed he would never be exactly the kind of superstar he was from 2012 to 2014.

But the other reason we don’t have that many mainstream Macklemore impersonators is that the most successful one happens to Broadway’s biggest songwriter.

The Hamilton problem

In May 2009, fresh off of the wild success of his Broadway debut In The Heights, the New York songwriter and playwright Lin-Manuel Miranda participated in something called the White House Poetry Jam. Performing in front of President Obama and various other important Washington figures, Miranda took the opportunity to debut some new material he was working on: a rap song about the life of Alexander Hamilton.

The song Miranda debuted at the White House became the opening number for Hamilton, and over the next eight years it became the dominant force in mainstream liberal culture. Hamilton quickly turned into one of the biggest Broadway shows of all time and the thing that finally got your parents to listen to rap. The show has gone through its own cultural cycle of massive popularity and backlash, but Over the next eight years, that song would slowly take over the world, or at least become the dominant force in mainstream white liberal culture. in 2016 its pull was so strong that artists as big as Nas and Alicia Keys appeared on a mixtape remixing the songs from the musical.

And sure, I like Hamilton enough — we all do. But listen to that opening number, particularly as performed at the White House stripped down to its bare parts: the dramatic descending piano line, the slightly overperformed expositional rapping. Does it not perhaps bring to mind a certain Seattle rapper telling you about the first time he unboxed a pair of Jordans?

The point here is not to accuse either Miranda or Macklemore and Lewis of ripping each other off. It’s more to say that the more-than-passing resemblance between “Alexander Hamilton” and “Wing$” illustrates a larger point about where Macklemore’s influence went in mainstream culture — it went to Broadway.

Hamilton is The Heist’s approach to rap storytelling as applied to Revolutionary War history, and Lin-Manuel Miranda is maybe the only nationally-known recording artist who delivers raps in the same theatrical cadence as Macklemore. It’s also easy to see how the mainstream success of something like “Same Love” might have set the stage for Hamilton to become the biggest cultural event of the late Obama years. People were primed to listen to quasi-spoken-word raps breaking down American Ideals. An audience that adored a song like “Can’t Hold Us” was primed for “My Shot.”

Critics were certainly drawing the connection between Macklemore and Hamilton early. In fact, when Macklemore & Ryan Lewis released their second album, Pitchfork critic Jeremy Gordon wrote that the single “Downtown” was “a Broadway song, basically—rap for people who loved Hamilton.”

And perhaps Broadway is ultimately a better home for Macklemore clones than SoundCloud or “Rap Caviar” or whatever. The clumsy heartstring-pulling and the spoken-word style delivery are pretty clear turn-offs for a general audience, but are perfect for a musical.

But crafting a form of rap music that can be easily transposed to Broadway also precludes that aesthetic from being cool. Think about what happened with the Sacramento rapper Hobo Johnson, who went viral for his 2018 entry to NPR Music’s Tiny Desk Contest, but whose actual recorded music was not well-liked by rap critics or fans, to put it lightly.

In a post-Lin-Manuel world, there was a clear ceiling on how seriously anyone would take this kind of stuff. Hamilton was huge, but no one who wants their music played in cars and clubs and dorm rooms necessarily wants “rap for Hamilton fans” to be blurbed in the press.

Ultimately this left Macklemore in a weird place, probably capped out of ever being a huge rap star again but also permanently outside of the dungeons of Pacific Northwest rap where he had lingered for nearly 10 years before The Heist.

Macklemore released his first Ryan Lewis-less album in nearly two decades last year. It’s called Ben and it’s exactly what you would expect — sometimes moving, sometimes preachy, often well-crafted. He still tours, he still has a ton of dedicated fans.

And for someone who came up through the Seattle underground, who clearly idolized artists who the Grammys would never dream of recognizing, isn’t that weird sweet spot between underground and mainstream, between saccharine and silly, exactly where Macklemore would want to be?

A decade on from that infamous Instagram post, Macklemore is ultimately occupying exactly the right place in the culture. It just took a Broadway musical and an ill-fated run-in with the Grammy Awards to get there.

A decade later, what was the deal with Macklemore?

On The Heist, Lin-Manuel Miranda, and the 10th anniversary of the whole Grammys thing

The Grammys are bad at rap and also weird

The Heist is fine, and Macklemore is Macklemore

The Hamilton problem

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