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Bossip Writer Talks Crafting the 2020 Election’s Most Anticipated Headline

President-elect Joe Biden and vice-president-elect Kamala Harris. Photo: AFP via Getty Images

It’s here. The headline we’ve waited four years for. More and more news outlets are calling the 2020 presidential race for former vice-president Joe Biden and California senator Kamala Harris (including @PopCrave), but none have been more anticipated than the headline from Black entertainment-news site Bossip. After a stressful week, soothed only by making memes about ballot counters and thirsting after cable-news data experts, the Bossip headline was set to be a massive sigh of relief.

Bossip headlines are known for taking the moment and making it even more over the top, hilariously adding to the discourse and often taking on a life of their own. But while they seem so meticulously crafted, the magic is in how natural they come to the small team of editors. Each author writes their own headline and for Jason Lee, a.k.a. “@hiphopobama,” the brainpower behind Bossip’s headline declaring Joe Biden the president-elect of the United States, it came to him like a rap verse. “We write long-ass headlines,” he laughed on the phone with Vulture. “I look at it like I’m writing bars.” He knew he had to do something special, something that spoke to the exaltation this would be online and stood out from the many, many nicknames Bossip has come up with for Donald Trump. “I mean, we’ve called Donald Trump everything orange. Pumpkin-spiced and dorito-dinged and habanero Hitler. We called him safety-cone orange, we called him burnt sienna. We ran down all the list of orange things.” And here’s what he came up with for Saturday morning:

“In the moment, I try to put in whatever effort I have into the subject and however I can turn a Rubik’s cube in my mind,” he explained his process. “But after it’s written, I try not to go back over it a million times and trying to fine-tune it because the whole point about it is for it to just be simple and easy entertaining.” After speaking with Vulture Friday night, Bossip officially called the election Saturday morning, with only a small edit to their original headline: They used “disenfranchiser-in-chief” instead of “soup cookie-in-chief” (a euphemism for “cracker”). On Friday, hours before we knew when election-results purgatory would end, Vulture spoke to Lee about how the highly anticipated headline came to him and the extreme hype around Bossip.

What went into the headline creation? How did the editors start thinking about it?
At Bossip, everyone kind of just writes their own headlines for the stories that they write and there’s not that many of us. There’s only eight of us on the editorial staff. For each story, everyone writes what they feel about it, and the general outline is just to obviously make it funny and adhere to a certain level of you know, Bossip-ism as far as it being over-the-top and alliterative and descriptive and whatever else you can toss into the blender.

What was your thought process like starting to think about what this headline would look like?
The only part that I had really was, “Hot damn, Joe, here we vote again,” just because it was in my mind. I approach a lot of these headlines like I’m rapping. So, that’s the only part I had in my mind as far as like a hip-hop reference that you could kind of flip and make it relevant to the situation. Everything else I just let it happen however it happens. Like, I was having a conversation with a friend of mine the other day, and she asked me what the headline was gonna be. And I was like, “I really don’t know.” Like, I just let the moment happen. And whatever I feel whenever the news breaks is kind of how I go for it.

Can you break it down?
“Hot damn, Joe, here we vote again” is just a Lil’ Kim reference. I like doing headlines where people will react to it and be like, I really sang this headline. I don’t think we’ve used “candy corn” yet. Maybe I’m wrong about that. But to me, it was an obvious one, plus candy corn is nasty as hell. Don’t nobody want no damn candy corn. I obviously took the “candy corn-colored” and made them all K’s. So, people can take what they want from that part.

“Dragged out of the White House by his flimsy faux follicles.” It’s a Donald Trump hair joke. I felt the opportunity to squeeze in some more alliteration, which everybody is always a fan of. The image of a political cartoon of Donald Trump being dragged out of the oval office by his hair is kind of what was on my mind.

Everybody likes T.I. for saying big words. I always feel with Bossip headlines it’s more of, I can throw in one polysyllabic word, and then maybe out of all this craziness that I’m talking about someone will stop and say, “Let me look up that word and see what that word actually means,” know it and have it on deck. Then it can be a thing where when they pull that word out sometime, it’ll be a thing where they learned that from Bossip. “Bang the gavel” was just following the wordplay of “adjudicatory” and, you know, we’re all judging Donald Trump. Everyone is judging Donald Trump. We’ve been judging Donald Trump ever since he stood at the top of that escalator and called Mexicans “rapists” and all these other crazy stuff. So, you know, a big part of this election is purging America of Donald Trump and everything that he’s brought. It feels like we’re literally living through the Avengers: Infinity Saga. Now it’s Endgame and everyone’s waiting for Donald Trump to turn into dust. Then, Donald Trump’s presidency is “raggedy” as hell. So, that one just goes without saying.

What feeling did you want the headline to evoke, especially after such a long week for everyone?
I approached this thing with the idea of a songwriter. So, in songwriting, you usually want to have a part in the song, whether it’s the hook or the verse that I call the crowd-participation part. You know, they play a song in a club and the DJ can drop the beat and everyone knows the lyrics of the song. That’s what you kind of want to get, that freeing feeling. So I wanted people to read it, and feel like they got their emotion out. But like I said, this is a judgment election. Even though it’s relatively close from what it looks like right now, I think people wanted to see America look at Donald Trump for four years and say, This is disgusting. We are going to wholeheartedly rebuke this. And, you know, America didn’t really do that. [Laughs.]

Were you ever worried about coming off too funny when things are feeling a little bit bleak?
Yeah, for sure. The thing with Bossip is that we write a lot. When Talib Kweli spent like 25 days harassing that woman on Twitter this year, the initial headline that I wrote wasn’t about being funny. And in my mind, I was like, okay, that’ll be the end of it. But people reacted to it so tough that I said, “Okay, I want to follow it up.” The whole idea with Bossip is that we’re supposed to be unflinching and kind of brutally honest and in a scathing way. If you do something stupid or there’s something crazy going on, we’re going to address it head-on. This isn’t a CNN or MSNBC or the Washington Post where you have to play it journalistic, straightforward. No, we’re gonna have attitude about it.

Did you think at all about a headline for if Trump got reelected? How would you have gone about it?
I didn’t think ahead of time. But if he would have gotten reelected, first, I would have gone to the exit poll because I spent most of last year calling Donald Trump “53 percent of white women’s president.” So, I will probably go to the exit poll to see where that number is now. Is it 53? Is it 59? Is it 65? Whatever that number is, I would reassign him a new number. So, he would have gotten that but most of my pointed criticism would have been at America. At this point, we all know Donald Trump is a piece of shit. I can talk about that all day. But for him to get reelected, it really would have been pointed at America specifically and truth be told, it probably would have been aimed at white women and Black men. And in this particular case, based off the early exit polls, honestly, I probably would have given the Cubans some smoke, too, like any minority group, any type of group that has been oppressed in any kind of way and still rolls with Donald Trump, like, I’m probably gonna try to find a way to give you a hard time about it.

What makes a headline a Bossip headline to you?
A Bossip headline needs to be over the top. That’s the first thing. It needs to be accurate as far as whatever details are enclosed. We report, obviously, on all kinds of stuff, so some of it can be rumor-y, but it definitely needs to be over the top. There needs to be some alliteration in there. There needs to be a good call back or pop culture reference. One that really fits the situation, but one that’s still obvious enough so when you say it that it’s not like some obscure thing that you’re trying to like, make “fetch” happen.

Do you have a favorite headline that you or someone else has written recently?
I think that probably one of the ones that had the most, I guess, exposure or retweets recently was the one when Donald Trump first came back and said he contracted COVID-19. And it was: “Make Antibodies Great Again? Perpetual Pandemic Denier, Petri-Dish-in-Chief, Maskless MAGA Moron, Egregious Epidemiological Equivocator, And Lung-Injecting Liar Donald Trump & Melania Test Positive for COVID-19.” “Make antibodies great again” was just a great line. Okay, we’re gonna turn MAGA upside down and we’re gonna have some fun with this MAGA. And petri-dish-in-chief was the one when I said that to myself Okay, I’m on the right track. He was going around, having all these rallies in places and then leave that city and then the COVID spike would go up, like the week after he leaves. I don’t know if it’s his fault or not. But we’re gonna blame it on him because why not?

I mean, it gets to the news of him going around with the virus in four words.
You’re reading this because this is the news and it’s funny. In the same way that you would watch Trevor Noah, or you’d watch your favorite comedian do a late-night monologue. That’s kind of how I try to operate.

I feel like, especially with Bossip’s political coverage, we’re so inundated by the news, seeing it in a silly, lighthearted way, a relatable way, is what everyone needs right now. What do you make of all the hype, where people are accosting you for this headline before the news is even official?
Like I said on Twitter, this really must be what Rihanna feels like. The people have been harassing her about this album that’s not come out for years. And like, I get it now, Robyn Fenty. I understand your plight. We can relate to one another. We should talk about our plight together sometime. But it does feel good, though, that people anticipate it to this degree because we’ve been doing it for a long time and the headlines have built their own reputation over the past five, six years, but Bossip has been around writing their own unique style of headlines since the very beginning. I’ve been at Bossip almost ten years now. When I came in, Bossip already existed in the blogosphere amongst that time when there was Media Take Out and Straight from the A and all these celebrity blogs were going on, Bossip was right there in the mix with everybody. And then it came to a point where all those sites had gone and disappeared and we were still here. I think a lot of that is just from, I wouldn’t say changing the voice, but taking what had already been there, that foundation of what Bossip is supposed to be and really pushing the envelope as far as we possibly could.

So, it’s cool to see people be excited about it. I already know that when I open sometimes my personal Twitter and when I open Bossip Twitter, it’s going to be filled with eyeball emojis and people like “Where’s the headline?” It’s gonna be filled with Judge Judy GIFs and it’s going to be like, “Hey, something just happened. R. Kelly just got arrested, what you gotta say? Bill Cosby is going to jail? What you gotta say? Donald Trump has COVID, where are you at?” I mean, it’s gonna sound very egotistical, but I don’t know anywhere else in the media space where people are anxiously anticipating. There’s a lot of popular media figures and a lot of people that have fans, but they are harassing us about it within minutes of it happening. It’s like, Whoa, bro, it just happened. Give me a second to figure out what the hell is going on. I like the energy though.

Bossip Writer on Crafting 2020’s Most Anticipated Headline