The problem with becoming famous for being an anti-woke rapper...

... is that you have to keep being an anti-woke rapper

"All that was once directly lived has become mere representation.”

-Guy Debord

“I was put here to upset you”

-Tom MacDonald

I want to talk about the box braids. He doesn’t always wear them. Sometimes he wears his long blond hair down, sometimes he puts it up in a bun. That’s when you know he’s singing a sensitive song, an earnest song, a power ballad. When his hair is down, he croons, pouts, expresses regrets. “I've been sober, I've been wasted, I spent most of my life in-between, I've been sorry, been mistaken...” You feel like he means it, or at the very least that he possesses that special Tin Pan Alley ability to convince you that he means it.

The box braids, near as I can tell, primarily come out for the rap songs. A classic case of White rapper self-consciousness. Do you doubt his authenticity? Do you question his sincere roots in this genre? Do you dare assume that a man from the Prairie provinces who shares a surname with a fast food restaurant lacks flow? Consider the braids. A White guy. With braids. Surely he must mean it.

Tom Macdonald is a carpenter turned journeyman pro wrestler turned aspiring hard rock frontman. He is a recovering addict with stories to tell. He’s got some regrets. It’s very clear that he’s the kind of person for whom becoming famous has long been important. By his own admission, he only started rapping because he couldn’t hit the heavy metal high notes.

Every White rapper is a novelty act. Even the most successful rise to fame thanks to their own version of the “can you believe it?” marketing logline. The Beastie Boys were White rappers… but they were hip? Eminem is a White rapper… but he’s hard and real? Macklemore is a White rapper… but he’s socially conscious? The contrast only works because of what’s unspoken… assumptions about what White people are like, for sure, but more so about what Black people are like. Regardless of rap’s ascendence to music industry hegemony over the past thirty years, “rapper” remains a racially loaded term, and talking about rappers remains socially acceptable avenue for White people to stereotype Blackness while pretending that we’re not. Far from subverting any of that, the White rapper, the exception that proves the rule, plays into it. Often quite lucratively.

Back when he was first starting his rap career, Tom MacDonald didn’t have the box braids. That was only one of his problems, though. He tried to go the Eminem route— betting that he had the technical chops and tough guy stare to pull off an air of hard-earned authenticity. That version of Tom MacDonald used to rap lines like this:

“I ain’t a killer, but don’t push me, I could change my mindI learned a thing or two in Compton about taking lives”

A pretty audacious statement for a fella from Edmonton, but I get it. You can take the wrestler out of the ring, but… you know how it goes. If you’re gonna make it in show business, you gotta create a persona.

He didn’t break through, though. Whether that was bad luck, insufficient skills or a hackneyed concept, I can’t say. What’s more, I can’t prescribe motive to another human being whom I’ve never met. A lot of things happened to Tom MacDonald between 2015, when he was rapping about being a Compton-trained killer, and 2018, when his career finally took off. Most importantly, he got sober. A blessing. A new beginning. You can tell he’s immensely grateful for that transformation in his life. He croons about it semi-frequently, at least when he’s braid-less.

The other thing that happened to Tom MacDonald after 2015, though, was an outward political transformation. And that too may have been earnest. A lot of people’s politics changed in those years.

All I can say for sure is that for a while, Tom MacDonald was rapping about how tough he was and not getting attention, and then he was scolding other rappers for their hedonism and getting a little more attention, and then he was rapping about how he was oppressed for being a White man and was getting a ton of attention, and then he was off to the races.

In 2022, MacDonald was the subject of a truly excellent Rolling Stone profile by Alice Hines. By that point, the Tom MacDonald cycle was already well developed. He’d braid his hair and release a new culture war bromide: maybe something about pronouns or abortion or flags or, more frequently, about a whole jumbled bouillabaisse of all of them mixed together. You know what’s the problem these days? They canceled all of the flags and replaced them with abortions. Makes you think. The details of the content didn’t really matter. What mattered was the provocation. He became a one man headline-generating machine. Tributes to his bravery in right wing outlets. Mockery in left wing outlets. Like clockwork, the view counts and streams would climb into the millions. The fame that had long eluded him as a wrestler, as a rocker, as a party rapper, as an earnest chronicler of his recovery story, was now his. Tom MacDonald had his White rapper “can you believe it?” elevator pitch:

He’s a rapper… but he’s conservative?

The core question of Hines’ piece for is, essentially, “does this guy mean any of this or is it all an act?” It doesn’t take much journalistic digging to find plenty of evidence for the latter. At the time, many of his songs contained anti-mask and anti-vaccine lyrics, and yet by all accounts he and his girlfriend were still, in 2022, dutiful maskers who took the pandemic incredibly seriously. The profile is full of contradictions like that— moments where MacDonald offers more nuanced opinions on abortion or race relations than you’d expect from his songs. And then there’s the matter of Macdonald’s pro wrestling past, and the lessons he might have learned from that chapter of his life. Wrestling is about heroes and villains, faces and heels. Being the bad guy often offers a more lucrative pathway to fame and glory than being the good guy. We all need objects of adulation, but not as much as we need a container for our rage.

Tom MacDonald was in the news last week. He pulled a stunt that I’m sure he knew would pay off handsomely. He recorded a rap song with Ben Shapiro, the fast talking conservative provocateur whose image (know-it-all nerd) is decidedly “un-rap” (in fact Shapiro previously made headlines for his purported hatred of rap, which is exactly the kind of sweaty “…now going door-to-door trying to shock people” move that has long been his bread and butter.).

It doesn’t matter what Tom MacDonald and the not-so-funky Ben’s song was about (I don’t know man, something about facts and how they don’t care about your feelings, and also about the flags again, and how they’re all rainbow now, plus about how MacDonald’s pronouns are “the man who don’t respect you,” which, honestly, sounds really unwieldy). The point was that BEN SHAPIRO, A MAN WHO LIBERALS LOVE TO HATE, WAS NOW RAPPING, WHICH IS NOT SOMETHING HE NORMALLY DOES. It’s spectacle for spectacle sake. And so there have been headlines and streams and an absolute Möbius strip of Youtube reaction videos begetting reaction-to-the-reaction videos and oh yeah Nicki Minaj is also involved for some reason and oh my goodness it is all so exhausting.

Returning to the question of whether or not Tom MacDonald believes any of his schtick, I mean… probably not? In any case, there’s just as much evidence that, whether he’s actively conservative or secretly liberal, at the end of the day he doesn’t actually care that much about politics at all. You can see it in how little his songs have evolved over the past few years. He really does keep rapping about the flags. And about how he is White, and how he assumes you hate him for his Whiteness. And about how the kids just have too many damned pronouns these days. A Tom MacDonald political song is basically just a Mad Libs exercise where he’s only allowed himself to fill in the blanks with five different search engine optimized “controversial” topics.

To be fair, Macdonald did take a stab at deepening his political analysis at the end of 2022, with a track called Dirty Money. It’s a mess of a song, but I don’t disagree with the general message (I think it’s about how politicians and corporations and media conglomerates just want your dollars, a topic that would have earned some “right ons!” from me back in my dorm room days). It mixes some elements that I, a triggered/offended leftist snowflake, don’t like (there’s some drive by Islamophobia) along with some others I agree with quite a bit (he admonishes conservatives for lionizing Kyle Rittenhouse). But regardless, when given an opportunity to explain the song to a then pre-rap-stardom Ben Shapiro, MacDonald demurred, saying, in essence, “man, I’m just a regular guy who doesn’t really understand any of this stuff; I think that’s why people like me.” He sounds bored. He’d rather talk about how hard he’s worked to reach fame.

If I were to develop a Unified Theory of Tom MacDonald, it would begin with that boredom. He cares much less about the topics that punctuate his viral raps than both the conservatives who champion him and the liberals he mocks. In between those songs, he continues to unbraid his hair and record earnest ballads about how he loves his girlfriend and is glad to be alive. But he must know that those songs won’t pay the bills. He’s stuck. Very few people want to hear from Tom MacDonald. Far more will tune in to the MAGA rapper. So that’s what he’ll be, for perpetuity.

I bring up the quagmire that Tom MacDonald has built for himself not to elicit sympathy. He’s doing fine, I’m sure. I wish him well. What matters more to me, though, is that the rest of us avoid falling into the same trap.

Before I get too preachy here, a quick acknowledgment. I’ve written more than my share of “let’s poke fun at the viral reactionary song” essays. They’re fun to write, and are always guaranteed to be amongst my most popular pieces. I have no doubt the conservative novelty hits will keep coming, and if I feel like I have something interesting to say about them, I’ll continue to write my silly little essays. We’re all just out here trying to have a good time and make an honest living, both the anti-woke songwriters and the woke jokesters.

The problem comes, though, when we mistake any of this for meaningful engagement with politics. The assumption—when we see somebody like Tom MacDonald flop around our timelines admonishing us for being snowflakes—is that he’s doing this primarily for an unseen mass of MAGA reactionaries who will somehow grow more powerful now that they have access to greater quantities of pop culture that flatters their worldview. We jump to mock and post our righteous take-downs as if doing so is somehow a brave, important act. Tom MacDonald is the Tiananmen Square tank. Our admonishments are the students standing in his path.

And yes, there is an audience for whatever it is that showmen like Macdonald are doing. He has genuine fans, individuals who apparently still aren’t bored with yet another song about how the good flags have been replaced with bad flags. But, as Hines’ Rolling Stone piece makes clear, Macdonald knows quite well that his success relies just as much on the outrage, on the think pieces, on the snide takedowns as it does with the pronoun hating true believers. In his own words, “I sort of realized that the people who didn’t like me were doing the most for me. They were the ones that were like, ‘I have to show 30 of my friends this piece of s***, because I hate him.’”

He’s doing it for us, is the thing. The haters. The snowflakes. The smarty pants who know how to critique him. He needs us. We are the woke to his anti-woke. He can’t exist without our attention.

The question, though, is whether we can exist with him and his ilk— the Ben Shapiros and Matt Walshes and Charlie Kirks and all of the other internet famous doofus-y firebrands. Do we actually need to keep critiquing them? I understand why it feels like we do. In a world where we so frequently feel lost and ineffective as to our ability to make the world a better place, I know full well the value of a quick hit takedown. You see that guy? The dumb and dangerous guy on the internet? I didn’t do a lot today, but I sure as hell made my friends aware of how much smarter I am than him.

I don’t know Tom MacDonald, but I wonder if there’s something that he secretly craves more than fame, if what he actually wants is to be seen, respected, and loved. Maybe I’m wrong. But if I’m not, then the self-proclaimed “most controversial rapper in the world” has built himself one heck of a gilded cage. He’s gained all the world, but has lost his soul.

I don’t care whether we on the left give Tom MacDonald more or less attention. My sense is that his whole deal is a pretty sustainable enterprise by this point. The algorithm already loves him, regardless of any of our individual decisions to feed or ignore the trolls. I just wonder how we avoid following his lead. When we take a quick hit social media action—either a takedown of someone we hate or a boost of somebody we love—what are we seeking? Not just immediately, but in the long term? Do we want the hopelessness to go away for just a second, or for longer? And if it is the latter, what would we do differently?

In all likelihood, Tom MacDonald doesn’t really have a choice any more. He’s stuck. But that doesn’t mean we have to be as well.

End notes:

Would you like a palette cleanser? Perhaps an example of a rapper who takes her politics (and community-centric political education) quite seriously and is willing to look critically not only at other rappers’ hypocrisy but her own as well? Let’s listen to some Noname! Specifically “namesake.” Lyrics!

With all apologies to Mr. Macdonald, I feel like those are slightly more thought provoking lyrics than “Where the American flags at? Remember when people would hang those?”

As always, the song of the week playlist is on both Apple Music and Spotify.