Please give Bossip a Pulitzer for its headlines

Assistant editor Aiesha Letman on how bastion of black excellence Bossip comes up with its hilariously heady headlines.

October 19, 2017
Please give Bossip a Pulitzer for its headlines Sharon Gong

Bossip headlines read like poetry. Crude poetry, but poetry nonetheless. They’re written with an artful precision that can either drag, expose, or celebrate a person through a mouthful of alliteration and phrases that will inspire you to make a better use of your vocabulary. For example, I won’t ever be able to hear “cakes” without thinking about the many times a Bossip headline has asked readers whether someone was getting theirs smashed into tiny smithereens.


Instead of sticking to safe syntax, the writers and editors at Bossip go for elaborate descriptions that build very visceral images. You might not know what a swamp possum is but when the mysterious mammal's size is used to describe a curvaceous woman, you know she must be thick. Recently, Bossip has turned up the meter on these crafty headlines, causing them to gain popularity and a strong engagement across social media.

Over the phone, Bossip assistant editor and headline genius Aiesha Letman, who's worked at the publication for three years, explained why the perception of entertainment blogs has changed, how long it takes to come up with a perfect headline, and how she came up with the phrase “bottlenose dolphin thick.”


Bossip has always had a strong voice in reporting entertainment news, but when did you all make the decision to pour more love into the format of your headlines? What brought on the revamp?

I think it naturally transitioned into this. It's something that unfolded because of our Bossip team and the way it works. When something works, we're going to do more of it and that's the formula. Internally, we have a strong team. We really like each other and our group chats are hilarious so it mirrors that energy, what we put in the stories.


When I first came around, [celebrities had] an attitude towards bloggers in entertainment. But with social media, celebrities have figured out we help them, we don't hinder them. So that makes us feel more comfortable that we can do what we need to do to report what they're doing. A lot of what we report on isn't that serious but it could be a headline and gain interest for the person. It's kind of a novelty at this point if you have a Bossip headline. People will always remember it. I don't know when the headlines came like this but it happened this year and I think it's because of the team.

So how do you all work together? Before you get to the headlines, do you toss around ideas in a group chat?

We wake up at the same time every morning and asked each other what news we've seen. There's a handful of us and we all have a niche too so I'll check it in a que. Or we'll put a headline in and ask if something makes sense and we'll put our spin on it.


Is there a person with final approval or a specific headline editor?

No, we can post whatever we want. This morning they wanted me to stop posting about Keyshia Kai'or but I made the headline nice and didn't include the worst tweets in the post. I wasn't mean to her but they were concerned about that. When it's things like that that are controversial, I ask first. We do have ads and sponsors, and we want to keep relationships. I know she's done several interviews with us and it's something that's happening so I didn't want to turn a cheek to it. I don't always feel pressured to come up with a funny headline. I've had stories that have gotten million of hits that weren't funny at all.

We all tweet our own stories. There's no one social media person. People always say the social media manager at Bossip needs a raise — well then we all do. You write your story, make sure you post it to Twitter because it won't get posted if you don't do it. We all have the password to Twitter and we make sure we put our stories up as soon as we finish them. We use social media as a tool as well and we’ll direct people to the right person if they send a DM but we're all responsible for the Twitter so we can also meet our goals and bring in views and make sure our numbers are up on the business side.

How long does it take to come up with a headline?

Probably like a minute. You know what the story is about and your start playing with it in your head. I'll do a normal one when it's in draft and then it'll pop in my head as I’m writing. We only have an hour-and-a-half to two hours to fill in 22 stories between five or six of us. So I have to hurry up and do it. With practice it comes easier. We have to make sure we're conscious of time when we're writing.

“It’s basically comedy in news form.”

Have you always been clever with the way that you put words together?

Oh yeah, I was the girl with the "Yo Mama" jokes. I'm going to clap back at you because I know you're going to clap back at me. I actually was on MTV show Yo Momma. The writers have weird backgrounds to how we got here. I've done improv, tried standup before and I didn't like it. I like what I'm doing now with writing because it's basically comedy in news form.

Tell me about the role of alliteration in writing a headline. It’s what seems to draw a lot of people in.

We knew that it worked when someone did it so it was like, "We're going to make sure that get these skills up when we put these headlines out, make sure they work and flow." That's the entertaining part because we teach people new words, and ways to put adjectives and verbs together. It gets the most traction when the alliteration is looking lovely.

Where do you all get the language from that you use in the headlines? It reminds me of stuff that my older aunties and uncles say.

[Laughs] The culture of Bossip was established long before a lot of us. It was already there and we know what the Bossip voice is. So yes, we're going to speak in that voice like an auntie or uncle and we're not going to be the dirty aunt or uncle unless you're the bae of the day. We just know how to use it. I’m not sure when it’ll be out but we're working on a Bossip dictionary with all of those sayings and it's going to be a thing soon.

You called a Bae of the Week Darnell Nicole “Bottlenose Dolphin Thick.” Where did that come from?

Because she is! I love her body. She's from Miami so I thought of dolphins and dolphins look like thighs a little bit. It's all about making it more visual and being more specific. In comedy, when your favorite comedian says something funny, it's probably because they've said something that other people haven't said out loud.

Let’s discuss the infamous “smithereens” word. Who came up with that?

Yes, “Smash those cakes to smithereens.” [Laughs] It was Charles Banks and he’s been on staff the longest. He's been there since Bossip started in 2007. He's been there when people wanted to fist fight us. When I first came on about 3 years ago, I did the Empire red carpet season premiere and nobody wanted to stop for me because of my mic. Lee Daniels came over and he said, "I love Bossip!" There were a bunch of white publications around me but he came he was talking to us first because he said we push the culture and we're crazy as fuck. [Laughs] After that people came over to me but it took one person to change people's attitudes.

Why else do you think the perception of Bossip has changed? Do you think it has to do with the headlines too?

It’s changed because people are realizing that your social presence is your currency when you're an entertainer. When it comes to you being on Bossip or in a headline, it's a novelty. It shows that we're paying attention, or you can get upset but it's still out there. I'd rather someone poke fun at me instead of laugh at me. I have such a better understanding of human behavior and forgiveness from what I do and I don't take any of it personal. I think celebrities are starting to understand that. We're all in the same industry — just on different spectrums.

Is there a headline that you like and look back to as a reminder that you can write a great headline?

It was about Tommie from Love & Hip Hop: Atlanta. I was being ridiculous. It's "Sloppy Toppy Seconds: Was Tommie Giving Caesar Her Wine Flavored Poon While Karlie Redd Waited Outside His Crib?"

Please give Bossip a Pulitzer for its headlines