P erhaps you’ve seen the music video for “Whiteboy,” which currently has more than 22 million views on YouTube and made a minor celebrity of a carpenter turned pro wrestler turned rapper named Tom MacDonald. 

It’s set in a Southern California classroom where the musician, who is white, wears blond box braids and sits at a desk in a row of bored-looking students. Just as he starts rapping about how he shouldn’t have to feel bad for being white, the students start to make faces and throw paper at him. The teacher, played by a Black actor, tries to quiet MacDonald down, waving his arms and wordlessly shouting. The rest of the classroom begins to taunt him: “White boy, don’t say that/White boy, you so bad.” MacDonald overpowers them with a scream of anguish, his voice rising above all the others in the room: “White boy, white noise, saying shit I can’t say with my white voice.” Naturally, there are viral videos mocking the song. “Cringing With Whiteboy,” a reaction video, is currently sitting around 1.6 million views. Almost as if it were an HBO Max original, MacDonald released an accompanying behind-the-scenes clip where he describes the concept of the song. He says that he wanted viewers to get pissed off. Those reactions, he hoped, would “spark the conversation.” 

But MacDonald started something more vicious than a conversation. Even if you’ve never seen the video for “Whiteboy,” you know precisely the type of person who would put it on repeat. He’d gifted the culture war a new text. Eventually, white nationalists discovered the song. MacDonald said he spent hours deleting their comments celebrating him. “That freaked me the fuck out,” he said, claiming that, as a Canadian, he was unaware of the chaos his track would unleash. Of course, he brought this upon himself. 

Four years after “Whiteboy,” MacDonald is eager to “show people I’m not just some brainwashed right-wing zombie.” When we spend time together this winter at his place, he’s ultra-paranoid about Covid, requiring us to stay masked and socially distanced even outdoors. He suggests that he isn’t against abortion, or gun control, that he watches videos about “intersectionality.” All of which throws me off. MacDonald’s music since “Whiteboy” has been a steady stream of ever-more-viral tracks trashing Black Lives Matter, fat acceptance, and whatever other liberal boogeyman was on Fox News that week. Although he also makes pop punk about breakups and moody tracks about sobriety, those never seem to blow up the same way. He acknowledges extreme positions benefit him. “I think a lot of people benefit from social unrest and civil conflict,” he tells me matter-of-factly.

“It’s the social media platforms. It’s the newspapers, it’s the magazines. It’s Fox News and CNN and whoever the fuck else — Rolling Stone.” It’s also Tom MacDonald, he concedes. “But like my whole thing is, like, be aware.” 

“Be aware” sounds a lot like “stay woke.” But don’t be fooled. In all of MacDonald’s body of work, his favorite target is wokeness.

Conversations about free speech and cancel culture have created a cottage industry for public figures willing to use language that many people might find offensive. At the highest valuations, celebrities like Joe Rogan have been able to build some of the most popular individual brands in America — in Rogan’s case, amid calls for him to be deplatformed for everything from vaccine misinformation to a number of since-deleted episodes in which the host routinely says the n-word. 

MacDonald is likely the most famous artist in a budding genre of his own creation: right-wing protest rap. On YouTube, songs with titles like “Snowflakes” (by MacDonald), “Rittenhouse” (by Tyson James, a “politically incorrect Christian”), and “Patriot” (by Topher, featuring the “Marine Rapper”) regularly go viral and even reach the charts, to the confusion or ignorance of industry players. One of MacDonald’s latest projects is a joint album with “hick-hop” rapper Adam Calhoun, released in February. Calhoun hails from Illinois and has a laconic flow and crude lyrics; he is to One America News Network what MacDonald is to Fox News. In his 2018 track “Racism,” he juxtaposes stereotypes among various kinds of white and Black Americans, using the n-word with impunity. Incredibly, the song remains on YouTube, where it’s been viewed 16 million times. 

“It’s not something I would have said,” MacDonald says of the n-word when I ask about working with someone like Calhoun. “But at the same time, I don’t think that automatically just makes you, like, a Nazi.” 

MacDonald, on the other hand, has so far avoided being meaningfully deplatformed. Perhaps because, since “Whiteboy,” his tracks have carefully danced around aligning with any particular point of view. Instead, they point out the supposed hypocrisy of others. In 2020, one of MacDonald’s tracks, “People So Stupid,” briefly bumped “W.A.P.” off iTunes’ top hip-hop spot. His Spotify and TikTok pages boast millions of plays, and his music errs on the side of internet-bred edgelord rather than overt far-right politics. If anything, he represents a new kind of online right, interested in liberal totems like rap culture. 

I tracked down the actor who played the teacher in the “Whiteboy” video, Adam Pepper. “I got so much backlash for that, trust me,” said Pepper. “But you gotta understand. I’m just an actor, and that’s my craft.” At one point in the video, when the classroom is on the verge of a riot, Pepper breaks down in tears — a moment that wasn’t scripted. It was difficult listening to MacDonald talk about how he felt discrimination for his “pretty blue eyes.” “As a Black man, with racism and the way police target us,” said Pepper, “you’re like, ‘What in the world? How could he say that?’ ”

At the same time, Pepper is adamant that MacDonald himself isn’t racist. In fact, he respects him as an “out-of-the-box artist.” Pepper has appeared in two more videos since and doesn’t think MacDonald believes much of what’s in his songs: “He says it because he knows it’s going to get some type of reaction.” 

MacDonald has critics on the right who don’t entirely trust that he’s one of them. Michael Knowles, a conservative commentator for the Daily Wire, took issue, in particular, with the fact that MacDonald cast a trans woman, Blaire White, in the role of a sexy video girl in his music video for “Snowflakes.” 

White is a YouTuber whose own channel also attracts millions of views for conservative takes on gender issues. In “Snowflakes,” White mouths along to lyrics like this: “He, she, his, him, hers, them, they/Screw a pronoun, ’cause everyone’s a retard these days.” 

One user on Twitter posted that it made them sad to see White used as a prop in a song that implied she was a man. White, for her part, saw the appearance as iconic. “I was the first trans woman in a rap video,” White claims when I reach her on the phone. She later clarifies she means openly trans — a claim that, at least in mainstream hip-hop, is surprisingly difficult to verify — “and even more interesting that it was a right-winger that made the video.” To White, the fact that MacDonald is blowing up is an indication that artists like her can win even on platforms like YouTube, which she believes censor conservatives.

What worries critics about MacDonald’s brand of creator is how it offers cover to people with straightforwardly dangerous ideas around white supremacy and other forms of bigotry. Sure, MacDonald has never put a Confederate flag in a music video, but he’s not afraid to collaborate with artists who do, and, presumably, reap the benefits of their audience. It’s Trumpian, in a way: having so many incoherent opinions at once that you never have to be held accountable for their implications. 

YouTube didn’t reply to requests for comment. Specifically, we wanted to know why it hasn’t taken down or demonetized videos like “Racism.” The company bans hate speech but has a different policy for borderline content, e.g., videos “containing inflammatory religious or supremacist content without a direct call to violence or a primary purpose of inciting hatred,” as its policy chief put it in a 2018 testimony to the Senate. She was addressing politicians concerned about the spread of extremism on the platform, and she reassured them: Borderline content, although not in violation of YouTube rules, would no longer be recommended by its algorithms. Comments, ads, and likes would also be removed.

After calling a journalist a slur, conservative commentator Steven Crowder was just one of many creators who saw his platform demonetized. So why aren’t white rappers dropping n-bombs getting hit? Aram Sinnreich, a professor of communication at American University, thinks YouTube’s policy is applied unevenly to music. “A hip-hop song isn’t getting flagged, unless it’s explicitly like ‘I love Hitler,’ ” he says. “Music gets a pass because it’s seen as a form of entertainment. We are justifiably very cautious about censoring art and limiting people’s entertainment options.”

I created a blank-slate account with a burner email on YouTube to see what the platform would recommend to me after MacDonald’s tracks. The algorithm dredged up everyone from Machine Gun Kelly, Yelawolf, and Dr. Dre to songs by lesser-known artists who were much more extreme than anything MacDonald has ever made. Take “Rittenhouse,” by James, which appears to call for the violent overthrow of the government: “Y’all about to make me pull a Rittenhouse/Bring the muscle, pull up at a politician house,” he raps in the chorus while brandishing an assault weapon. The debut of the video featured an insurance ad.

“He fucked up somebody else’s life. Championing him? That’s fucked up to me,” MacDonald said when I asked him about the video.

A generous interpretation would be that MacDonald is perhaps clumsily trying to find common ground. Take the track “If I Was Black” as an example. It was released as a mea culpa of sorts, one year after “Whiteboy.” “If I was Black, I won’t lie, I’d be scared to walk at night,” MacDonald raps. “The whole neighborhood is trippin’ like I’m out committin’ crimes.”

A less generous interpretation is that the track is “digital blackface,” as Sinnreich puts it. In the video, MacDonald superimposes his voice onto Black faces and bodies, and vice versa. Meanwhile, he raps in a “blaccent” that “signifies Blackness in this kind of racially grotesque way,” Sinnreich says, “that could only exist within the post-minstrel hothouse of American musical culture.”

MacDonald called the digital blackface characterization ignorant. “The whole song was about unity and using your imagination to try to see the world through someone else’s eyes,” he says.

I asked Adam Pepper, who played one of the Black Panthers in “If I Was Black,” what he thought. “I don’t think Tom was doing blackface,” he said. But he agreed with another of Sinnreich’s points: “Tom’s music flirts with neo-Nazi. It flirts with white power. I think sometimes he puts Black people in his videos to make it easier to digest.”

Oh, my god. The fucking Republican rapper guy just told me to put a fucking mask on.”

MacDonald has carved a niche the music industry didn’t think existed. Like an episode of Tucker Carlson Tonight sped up and set to a beat, his top-performing songs are an ice cream sundae of grievances: everything from #MeToo to body positivity to abortion to gay pride to white privilege. It’s appealing to a new demographic. “You might not consider yourself someone who cares about a rap song that’s climbing the charts,” Fox News host Martha MacCallum said on her show recently. “But it’s a pretty interesting culture moment when the tune is called ‘Fake Woke.’ ” “Facts don’t care ’bout feelings” goes the chorus, quoting a line by Ben Shapiro, a conservative pundit who famously claimed that rap “is not actually a form of music.”

“It’s human nature to listen to the negative,” MacDonald tells me. “Pretty quickly, 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 shit, because I hate him.’ ” 

And despite the concerns of his critics, he is part of a growing trend in music, as video-driven platforms like YouTube and TikTok become viable avenues to grow a fan base. MacDonald’s numbers aren’t astronomical in terms of major-label superstars, but they’re competitive, especially considering that he has no PR team, label, or even manager. He produces the beats for his songs, and he makes music videos directed by his girlfriend on sets built in various places around their home. 

And yet he has attained a level of celebrity — he has fans who decal their trucks with his face — that some artists with institutional backing never achieve. “As many people that hate [a song] with a fiery passion, there usually are others who love it with that same fiery passion,” MacDonald says.

It’s raining in L.A., and my feet are soaked with drizzle. A few hours ago, a wind gust knocked out a stretch of the fence bordering MacDonald’s backyard. And yet, here we are, outside and socially distanced for the past eight hours, and it’s going to stay that way. 

“Oh, my god. The fucking Republican rapper guy just told me to put a fucking mask on,” MacDonald jokes. He’s wearing a Balenciaga hat, a puffer coat, and a black KN95 mask that covers up piercings and face tats. The mask part wasn’t a joke. I put it back on. His video director and girlfriend, Nova Rockafeller, cackles extravagantly, maybe nervously. 

When I meet MacDonald at his house in the L.A. suburbs, he’s getting ready to shoot a new video, “Whiteboyz.” Learning from the past, the track attempts to repeat his former viral success. But “we have to be careful. We don’t want to attract the wrong kind of white boy,” he says. He has the sort of crusty rock-star look that we’ve come to expect in pop culture. MacDonald’s style is what you might describe as tactical Lisa Frank: flamingo-print shorts, bulletproof vest paired with rainbow cartoon-print leggings. Like a character out of Spring Breakers. 

During our conversations, he’d often walk back a perspective that seemed obvious from one of his songs. For instance: “I never said that I was anti-abortion. I was just looking at it.” The line in question: “Bacteria’s life on Mars, but a heartbeat isn’t life on Earth, like weird.”

He admits that he sees systemic anti-Black racism as a real issue. When I ask MacDonald for examples of anti-white bias, he’s pensive. White people are not necessarily victims, he says emphatically, seemingly walking back a core message of his songs. But the problem with calling them privileged is that it discounts “a whole group of white people who are, like, ‘Well, what about me? My life’s fucked up. The system held me down.’ ” 

“I’ve also done a lot of stuff that’s not politically charged, but that doesn’t seem to get digested and championed the same way, for obvious reasons.”

MacDonald grew up in Edmonton, Alberta, a city of a million inhabitants in central Canada where the average high in January is 20 degrees Fahrenheit. His dad was a contract negotiator for oil rigs. After high school, MacDonald worked in construction, specifically carpentry. When he wasn’t building houses or on rigs, he performed in pro-wrestling matches on pay-per-view, wrestling against ex-WWF competitors and touring on Canada’s professional circuit as All-Star Tom MacDonald. 

His viral fame started with a song called “Dear Rappers,” in 2017. It attacked so-called mumble rap, which he claimed focused on money, cars, and getting fucked up. According to MacDonald, commenters responded that he was racist for speaking condescendingly about rap culture as a white person. Thus, a cycle was born. His follow-ups to “Whiteboy” follow a predictable pattern: “Everybody Hates Me,” “Straight White Male,” “Politically Incorrect.” 

In pro wrestling, the good guys are known as babyfaces and the bad guys are known as heels. It’s all scripted, and some observers have compared the us-versus-them mentality to American politics. “The role of a heel is to get ‘heat,’ which means spurring the crowd to obstreperous hatred, and generally involves cheating and pretty much any other manner of socially unacceptable behavior that will get the job done,” writes Mike Edison in The Baffler, in an essay about pop culture’s greatest heel of all: Donald Trump. 

I ask MacDonald if he is playing a role. He’s not performing, he replied. “I am a heel. That’s my resting state.” In one of his early matches, MacDonald put a metal garbage can over his opponent’s head and beat it with a chair. He had a long-standing “feud,” or scripted rivalry, with a friend. He was once hit in the face with a golf club that severed a slice of his ear. That match paid him just $40. 

MacDonald monetizes new releases on his YouTube channel, and virality there fuels digital downloads and physical album sales. He has more than a million monthly streams on Spotify and says he sold 48,000 physical copies of his album with Adam Calhoun within the first week. He hired his mom, dad, and sister to pack and ship a warehouse worth of CDs at $15 apiece. 

MacDonald’s girlfriend and video director, Nova Rockafeller (born Paholek), grew up between Edmonton and Jamaica. She has a barbed-wire tattoo encircling her neck, and at one point performed at the Gathering of the Juggalos. (LA Weekly called her “violent but talented” in 2013 after she told them she’d punched 25 people in the face in her lifetime.) “I think of those crazy white boys,” she says. “Like the 16-year-old kids, lighting fires by the river.” We’re in the backyard of their suburban house in L.A.’s San Fernando Valley, describing the kind of white boy they’re hoping to speak to. “Like, what was that thing Zuckerberg was riding?” MacDonald asks, referring to the viral video of the Meta, f.k.a. Facebook, founder on a hydrofoil, holding an American flag.

If you were to absent-mindedly scroll through MacDonald’s Instagram, you’d have a hard time figuring out he’s been staying almost entirely inside for two years. MacDonald rarely posts masks on his social media accounts. When Rockafeller does, she avoids reading the comments. Their precautions aren’t a secret, but they’re also not obvious. “New people showing up on a constant basis, ‘Like, just saw fucking “Fake Woke” ’ and are like, ‘Fuck the system,’ ” MacDonald says. “And you’re like ‘OK, well, whatever, welcome to the team.’ ”

Rockafeller’s fear of dying from Covid is so acute that at first I think there’s no way I’ll ever be able to meet MacDonald in real life. She tells me she still wipes down all her groceries and holds her breath to check her mail on her suburban street.

She and Macdonald build elaborate sets in their garage, spare room, and backyard. One is a mental asylum, complete with padded walls and fluorescent lighting. Another is an apocalypse bunker. There’s a Mad Men-esque living room with a bear rug and roaring fireplace. For one video, he bought a vintage car that’s still in the front yard.

One evening while I’m in L.A., MacDonald hosts one of his weekly livestreams on Discord for a couple of hundred of his die-hard fans. A 15-year-old from Indiana is asking for relationship advice. 

MacDonald has written dozens of songs about sobriety and mental health, and many of the fans on this livestream say they like these songs better than his more viral political tracks. At times, he seems to regret his trajectory. “I’m not just the white conservative rap guy,” he tells me at one point. “I’ve also done a lot of stuff that’s not politically charged, but that doesn’t seem to get digested and championed the same way, for obvious reasons.”

Growing up, MacDonald’s favorite wrestler to watch was Stone Cold Steve Austin, whose shtick included guzzling beers and occasionally beating the shit out of his boss, the then-WWF chairman. But the anti-establishment wrestler also sometimes played the hero. MacDonald recalls a moment when, as a child and bullied at school, he saw a match between Austin and the Undertaker, pro wrestling’s terrifying undead zombie. “Steve Austin came out, and he was like this little six-foot dude with a shaved head and, like, didn’t have the pageantry,” MacDonald recalls, unexpectedly starting to cry. “As a child that spoke to me. To see a person go up and fight in spite of the fact that they would probably lose.” Steve Austin won that day. A few years later, he’d gut-punch — a.k.a. “stun” — Trump himself, during one of the future president’s appearances promoting his show The Apprentice. 

I get the call that my husband has Covid while driving to watch MacDonald shoot a music video for the upcoming album with Calhoun. I’m alarmed but not exceedingly worried. Omicron is hitting New York, and half the people I know are getting positive test results.

Now Rockafeller is scared. “Alice had three tests, babe,” MacDonald says, reassuring her. 

MacDonald empathizes with the Covid anti-maskers. “Sometimes I feel bad,” he says. “A lot of my followers are out protesting mandates. And yo, that’s so dope. I’m proud of you for fighting for your freedom. I wish I could be out there with you. But I can’t.”

Rockafeller’s asthma has always been severe. She’s ended up in the hospital after catching a cold. It’s radically shaped the couple’s approach to Covid. “All these people are like, ‘Masks don’t work, gotta fight the power, blah blah blah,’ ” MacDonald says. “You didn’t watch your girlfriend almost die three times this year, from breathing shit. Like suck a fucking dick.” 

Because of my visit, Rockafeller had decided to finally get her first Covid-19 vaccine. MacDonald wasn’t a fan of the idea, but ultimately he supported her decision to do it. The nurse came to their house. When the shot was injected, Rockafeller blacked out from panic. “I caught her after she fell into the doctor’s shit,” MacDonald recalls. “And I dragged her out to the front lawn and woke her up.”

Rockafeller wants MacDonald to get vaccinated, too, but he’s reluctant. He’s had health scares before, been misdiagnosed by doctors. The vaccine was likely safe, he thought, but only when you compare it to Covid-19 — which they were successfully avoiding by seeing no one.

That evening, I’m eating dinner alone in my trailer while the couple set up for the outdoor video shoot. MacDonald calls me: There’s a problem. Rockafeller is panicking and hiding in the shower. The reason: When we shoot the video, she’s realized, MacDonald won’t be wearing a mask. How can she be certain I won’t give him Covid? 

“Once fear ignites, it burns brighter and hotter and bigger at a rapid rate,” MacDonald says cryptically. “You’re experiencing negative thoughts as if they’re reality.” What was Rockafeller feeling right now? “Anxiety. Wondering. Not doing much. Probably crying in bed trying to calm herself, probably overreacting to symptoms that may or not be there. I’m not her, though.”

I wait for an hour, doom-scrolling about Omicron on my phone. I listen to the trailer generator hum, thinking about what it must have been like to spend 20 months inside.

In an hour, I get another call from MacDonald. Rockafeller’s still panicking, but she’s decided to go through with letting me watch them shoot their video, if only because she doesn’t have much of a choice. One condition is that I’ll need to stay at a farther distance. 

I sit 30 feet away from them that night, so much farther than planned that I might as well be watching the performance on an iPhone screen. The set has been designed to look apocalyptic: army-navy supplies, a crumpled map, brick wall covered in blood-like red paint, window boarded up with distressed two-by-fours.

I can’t hear every word they’re saying, so I place my recorder on the floor by the set, a prosthetic ear. I gather this much: In a tiny pocket of reality in this backyard in suburban California, a whole world is hiding, one where America is in flames and the good guys are living in abandoned buildings as they fight for their survival against the tyrannical forces of feminism, communism, and abortion. 

In between each take, MacDonald puts on a new mask. 

Alice Hines is a writer in New York and a Vice News correspondent. Trending Stories