Cheyenne Roundtree has always been a bit of a rolling stone (Human Pursuits 12/12/22)
Rolling Stone’s Entertainment Reporter on Kanye West, keeping it country, travelling to Canada, the best of Bravo, and opening yourself up to opportunities
VANCOUVER – It’s easy to forget, between praising Hitler, attacking (and then apologizing) to George Floyd’s family, hiring (and then firing) alt-right shit stain Milo Yiannopoulos, getting dumped by Adidas, announcing a 2024 presidential campaign, and breaking bread with a noted white nationalist (and a twice impeached president), that Kanye West told people he wanted to fuck his own shoes. It’s a small detail in the grand scheme of things, a dead star in the constellation of pain that has formed around West in the weeks since he decided to wear, and dress Yeezy models, in a White Lives Matter shirt. And yet I was struck by the utter Kanye-ness of it, of the power dynamic involved when someone demands they be taken literally, even at their most outrageous.
I was also struck by the quality of the reporting. With the help of some high-quality sources, Rolling Stone reporters Cheyenne Roundtree and Matt Sullivan had documented a crucial period in Kanye West’s career – one that soon drew to a close, in part because of their reporting.
Clearly, Cheyenne and I had a lot to talk about.
Our conversation, which has been edited and condensed for clarity, covered her early days of entertainment reporting, her brief time living in Missouri, her reluctance to lay down roots, the sweet smooth brain hours of the Bravo Extended Universe, and of course, Mr. West.
ES: How’s everything going?
CR: It’s good. It’s another day of reporting about Kanye West… I’m so over it.
ES: Oh my gosh. What are you working on?
CR: Um… [laughs] I can’t really say right now but basically just continuing coverage of everything that he’s been up to recently. I think he’s having an interview with some Twitch streamer later today, so monitoring that.
ES: I wasn’t going to start with Kanye, since I can only imagine what it’s been like to be part of this news cycle… But how did you find yourself on this beat? It sounds like you’re kind of tired of it.
CR: I’m not tired of it. I think it’s the idea that consuming so much awful stuff takes its toll. Every day he’s doing something completely unforgivable and so it’s kind of like “Oh my gosh, how did we continue to cover someone that continues doing the same thing?”
I got on the Kanye beat because he was doing his school, Donda Academy. First of all, I didn’t know he had a school. The pictures of the school showed the kids in all this Balenciaga and GAP gear in this warehouse. I thought “What? Who’s even at this school?” So I started learning about the school and building up sources. When everything hit the fan in October with the White Lives Matter show, I was already talking to people who were familiar with Ye, or Kanye, and that opened up an avenue into the rest of the reporting.
ES: What was your relationship with Kanye before all this?
CR: I was never a die-hard Kanye fan. I know all of his music, I listened to all of his albums. I started falling off around the DONDA release with Marilyn Manson popping up, and Da Baby. It made me step back and be like, “Whoa what is this artist actually supporting in his real life?” From there I’ve had a little distance. And then the last two years it’s just completely gone wild.
ES: What has stuck with you the most, in terms of everything that you have already reported?
CR: It’s always interesting when someone is so big and has these small moments of their personal life revealed to you. For me, it was the idea that Kanye’s really accessible to a lot of ordinary people. With his Yeezy fashion line, he worked with designers, but he had people that invented Dome structures for him. A lot of just random, ordinary people would say “Kanye texted me today to come work for him, and we were really close for this period of time.” That was really surprising, that someone you wouldn't think had any connection to him was on a texting level with him – even if it was for a short amount of time… They were always fired for some reason. But I don’t think anyone would expect him to provide that level of access.
ES: Right, the sort of 1-to-1 connection.
CR: When you think of big celebrities, especially people like [West’s ex-wife] Kim Kardashian, that have a huge amount of people in between them… There was no big buffer… It was, like, regular entry-level employees.
ES: There was a lot of sort of explosive stuff in your reporting around Kanye’s time at Adidas… Including him literally wanting to fuck his own shoes.
When you're talking with people about this stuff, is there a sense of disbelief around the stuff he was doing or was it normalized?
CR: It was a bit of both. It’s kind of like your crazy friend that does crazy stuff all the time. It’s hard to pinpoint one thing when you look back… In the moment they acknowledge this sense of disbelief. But then it’s chalked up to “This is just who this person is” and this is like one of the many things that they’ve done. Obviously, the shoe-fucking comment stood out to a lot of people, but people tell me “There’s all this crazy stuff that he would say,” and it was all lumped in together in terms of Kanye being Kanye.
ES: You’ve covered a lot of artists and celebrities who have cults of personality around them… Kanye, Elon Musk, XXXTENTACION. Have you received any blowback for that?
CR: I’m a black woman. And a lot of the people I talk about or write about, that are doing bad things, are black men or black musicians. Some of the criticism I’ve been getting is that I should be protecting black men and questioning why am I choosing to report on this sort of thing. And that sucks just because I feel like that shouldn’t even be part of the conversation.
ES: Has that been hard for you to deal with as your career has picked up momentum, going from Daily Beast and now to Rolling Stone? Like I imagine you’re maybe reaching a bigger audience. You’re also quite young.
CR: I’m not that young, I think it’s just my moisturizer doing a lot of work.
Honestly, I just kind of tune it out. I know everyone says that but... I don’t think it deters me. You know, you click on these profiles and it’s anonymous people or people that say that sort of thing every day to anyone that criticizes someone that they like… I would pay more attention to it if it actually was valid criticism, but it’s not. It’s just trolls.
ES: I know that within the industry, the idea of being an entertainment reporter is sometimes met with mixed reactions because people assume that the stories are just fluff. Obviously, what you’re doing is more investigative but is this sort of reporting something you always aspired to? Or did you just fall into it?
CR: It’s something I fell into. I always knew I wanted to be a reporter or writer in some sense. My first job was actually with The Daily Mail. It was out of college. So I worked with them for a bit and they have this really small exclusives team. It was either political exclusives or showbiz exclusives. And… I just am not very good at getting exclusives from political figures. So I went the showbiz route and then from there kind of really leaned into the entertainment side of things.
It is considered reviews and commentary and pop culture stuff, which is a lot of it. And I enjoy that as well. But I did feel like there was a little gap in the market, in terms of covering these figures in the same way we cover anyone else that is influential in our society. There are a lot of great journalists that cover lawsuits. But can I actually pay attention to the discourse and follow something that seems fishy, to see what turns up there?
ES: Did I see that you went to university in Missouri?
CR: Yes.
ES: Are you from Missouri originally?
CR: I’m from Dallas and I just wanted to go to a journalism school, so that’s how I found myself up in Missouri. I’ve only been back to the state once after graduation.
ES: I was going to ask! What was that experience like for you?
CR: It was really good. I mean the programs really great… I was thinking I would go the magazine writing route, and I luckily ended up at Rolling Stone. But college is honestly such a blur. I interned for Seventeen, so I moved to New York for a semester and then came back. I was just trying to get to New York as fast as I could.
ES: Dallas happens to be the sister city of Edmonton which is where I’m from originally. That’s oil country there!
CR: So I lived north of Dallas. It’s a little suburb. The slogan used to be “Keeping it country”...
ES: Hell yeah.
CR: It’s so not me, but it was really nice. I go back several times a year. I have a lot of friends there still. I call it pre-New York and after-New York. Fond memories, but it just wasn’t where I wanted to be.
ES: You’re a wanderer, you’re not laying down roots in your hometown.
CR: I used to only live out of two suitcases because I never liked to put down roots. It was only during COVID that I got actual furniture… I had no belongings except for some boots and coats and clothes.
ES: Oh my gosh. That is a very romantic 1970s journalist vibe that you’re cultivating over there.
CR: I think it's just laziness! I didn't see any purpose in buying furniture, especially in New York where you move every year. I was like, “I could just buy a new mattress on Amazon for 100 bucks, I don't care.”
ES: Are you really moving apartments every year? I would not have the fortitude...
CR: Honestly, almost everyone moves apartments every year until they find their dream place. In 2021 I finally moved into an apartment where I stayed for two years, and then I moved again six months ago. It’s rent-controlled so I shall be staying!
ES: I was creeping your Instagram and I noticed that you travel a lot. What is the itinerary looking like for next year?
CR: For the holidays I’ll be in Dallas and then I’m going to London for my friend’s 30th birthday. Some friends are also hopefully getting married in Italy which will be fun.
ES: Is Rolling Stone pretty generous with time off or is it just the standard three weeks?
CR: They’re pretty generous. I also plan around public holidays, try to wiggle it to 10 days, even though you’re technically only taking seven days off work.
ES: What is your favorite travel destination that you’ve been to so far?
CR: There’s nothing that stands out in terms of uniqueness. I thought when I went to Dubai that was pretty unique, but I have a lot of friends from London who tell me Dubai is where they went to in, like, middle school with their families. It's like, not that cool.
ES: [In a bad British accent] You're not that original, luv!
CR: I don't know if you watch Love Island but they all go there. But I don’t know, I really want to make my way over to Iceland next year, and I’ve been trying to get over to Asia forever, but that’s a long flight. Where have you been?
ES: Hm, I've been to Japan.
CR: How was that?
ES: It’s incredible. I would highly recommend it. And Vancouver is the gateway to Japan, so you can stop here, too.
CR: I’ve never been to Canada.
ES: It’s such a cliched Canadian thing to be like [in a bad Canadian accent] “Oooh have you been to our country?” But yeah what is your perception of Canada – or do you even think about Canada?
CR: One of my best friends is Canadian, and she's from Vancouver. Pauses. Actually, no, she's not. She's from Ontario.
ES: Where’s she from in Ontario? I’ve lived in both.
CR: I have no idea. She lives here [in New York City], but yeah… Good vibes. Apparently, there’s some great wine country up there.
ES: Yeah Ontario’s got wine. If you want mountains, Vancouver’s got that… Our dollar is really shit right now, so you'd be living like a queen.
CR: And the lakes are really pretty as well.
ES: Super pretty lakes in Ontario. It’s a good time, but I would never encourage anyone to come here if they didn't want to.
CR: I mean, I should at least get to Toronto. It’s close by.
ES: Is New York your forever home? You seem to really like it.
CR: I do love it. Forever is a long time… I think whenever you start to think about buying a house, or you wanna have kids, you wonder “Does this one-bedroom apartment support all those things?”
ES: I forgot that Cheyenne is a little reluctant to lay down roots.
CR: Laughs. It’s not that I'm reluctant… I just can’t see further than a year or two ahead.
ES: Why do you like having life open-ended like that?
CR: I like the idea of not knowing where things could go. I don’t like the idea of closing myself off from opportunities before I even know what they could be.
ES: You’re so open-minded.
CR: But I’m not.
ES: Did you always want to be a journalist? I only ask because I kind of fell into it… It just sort of happened.
CR: I knew I wanted to work for a magazine or something… In fifth grade, we had this project we were supposed to create our own zine or magazine. It was the best assignment ever and I took it to heart. My mom still has it… I also don’t see what else I would be doing, if not journalism, you know what I mean? People say “I’m sure you can pivot to other industries” but why would I?
ES: There’s just something about the journalism lifestyle that I am addicted to. I love that my job is talking to people and then listening to those interviews, or getting to ask people questions. There is a power that comes with that… It’s a crazy thing.
CR: For me, one of my favorite parts of it is, like you said, the addiction. There’s a certain high when you get a piece of news where you find out information and you're able to put it in writing… There’s an adrenaline rush that I wasn’t expecting when I first got into journalism.
ES: What are you doing to destress after a 6,000-word Kanye West article comes out – how do you find your center?
CR: Reality TV [laughs] I love Love Island. I was watching Winter House and Summer House but I kind of trailed off after last season. I’m a big Bravo girl. I don’t know if you watch Below Deck.
ES: I love Below Deck. That was our pandemic watch… We call it smooth brain hours. Something to just wash over you.
CR: That’s exactly what I do. I’ll revisit favourites like Girls or Sex and the City, stuff like that… This is a hot take, I don’t like British Bake Off.
ES: I don’t watch British Bake Off much but when I do I find it very comforting.
CR: I just like a source of conflict every now and again. Everyone [on that show] is just so nice, which is great, but I need conflict, versus a cake not rising, or something.
ES: The one issue I have with the Bravo universe is that very few things hit the high of the original Vanderpump Rules, so you're always chasing that dragon… It was just an incredible moment in time. The Real Housewives of Salt Lake City gets kind of close…
CR: Vanderpump Rules is one of my most favorite. I don’t even have words to describe how good it is. My TikTok feed knows exactly what I like. They’ll just show old clips of [VPR], old school Real Housewives of New York where Bethany is ripping into Ramona or whoever. I go down the rabbit hole of watching whole episodes. People will upload 10 parts of one scene.
ES: When I interviewed Joe Hagan from Vanity Fair, he had a great story about one of his first big assignments… I was wondering if you could tell me about the first piece you did that was cool, or made an impression.
CR: One thing that… almost deterred me from this line of work. In college, they make you do a shift at the newspaper desk. It was a Saturday morning and they wanted me to do an obit for someone. I started calling people up. I was like 19 or 20, and… They didn't know [the person had died]. I was under the assumption that they knew.
ES: Oh no.
CR: It was the first time that it registered with me… How my interactions with people… How you craft things… Really makes a difference… It was the first thing that made me be like, “Whoa, do I actually want this level of responsibility?” Because it was just an awful day… That was the last obit I ever did.
ES: What is life at Rolling Stone like these days?
CR: It’s been really good. I joined in April. So it’s been eight months. I think the people are insanely talented. Everyone’s really cool. I love it and I hope to stay here for a very, very long time.
ES: It kind of has a reputation of being a club for old white men. What has your experience been like with the magazine? Do you feel like that's changing?
CR: That maybe could have been the case a couple of years ago. Internally, I know there are a lot of young people, and people of colour that write. Rolling Stone has a huge Latino fan base and writers that write about Latino artists. I think that we’re trying to change that perception… Especially as we push more online coverage. We just did a creators issue of MrBeast and a lot of like Internet personalities that really break that stereotype. So hopefully it starts working.
Cheyenne Roundtree is Rolling Stone’s entertainment reporter. She lives in Brooklyn.