Wendy Williams and Don Lemon on Cancel Culture, Fame, and Legacy

Wendy Williams doesn’t just spill the tea—she sprays it. For more than two decades, the irrepressible media personality has surfed the airwaves on a swell of gossip, candor, and the unapologetic belief that if it’s on her mind, it should be on ours, too. First, as a DJ on New York radio stations such as Hot 97, and now as the host of her nationally syndicated daytime talk show, The Wendy Williams Show, the 56-year-old New Jersey native has built her career on a foundation of dish, drive, and, yes, drama. There was her 2003 radio interview with Whitney Houston, in which she continuously badgered the singer about her rumored drug problem, causing Houston to proclaim, “If this were back in the day in Newark, I’d meet you outside.” There was also her 2013 beef with Lil Kim, which involved, among other things, La Toya Jackson, Biggie Smalls, and a series of expletives too salty to publish here. And then, of course, there’s “Hot Topics,” the salacious opening segment of The Wendy Williams Show, during which she openly speculates about who did what where and with whom. Williams’s willingness to broach any topic has extended to her own life, particularly when it comes to her plastic surgery and struggles with cocaine addiction, which she has chronicled in books, a documentary, and a Lifetime biopic. In 2019, Williams found herself at the center of her own tabloid maelstrom when the dissolution of her 21-year marriage played out publicly. “It’s crazy ’cause now my business is your business,” she said at the time. As she tells the CNN news anchor Don Lemon today, that’s just the way she likes it. — BEN BARNA

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DON LEMON: Wendy, how do you want to be remembered?

WENDY WILLIAMS: As the one bright spot in the middle of an otherwise complicated day. When people think of my name, I want them to smile.

LEMON: Do you think people do that?

WILLIAMS: Secretly.

LEMON: Why secretly?

WILLIAMS: Because people who say they don’t like me, I know they do. You watch the show. I make you laugh. But you’ve got to find some reason to continue with toxic thoughts.

LEMON: Do you see yourself as part of a community of talk show hosts, or do you see yourself standing out from the pack? Who is Wendy among talk show hosts?

WILLIAMS: I’m over here while they’re all over there. And I don’t mind that because my entire life has been that way.

LEMON: You’re almost sounding like, “I’m an outsider, and I like being an outsider.”

WILLIAMS: I do like being an outsider.

LEMON: Do you learn from watching other hosts?

WILLIAMS: No. I was a fan of daytime talk, which is a very specific part of the TV culture. To be a part of it now, there’s nothing to study from other people. Just come in and be yourself.

LEMON: How much attention do you pay to other talk show hosts?

WILLIAMS: I still watch as a fan. I love talk shows, and I love the judge shows. At first, I was competitive with others. It was difficult for me to have a guest not stop by the show first. And then I realized that it’s not about who does it first. It’s about who does it best.

LEMON: You’re right about that.

WILLIAMS: Also, I like to see what the girls are wearing. I like to see what the guys are wearing. And I compare my wardrobe only in terms of, “Yup, Willie [Sinclair III, Williams’s stylist] is still pulling the best stuff.”

LEMON: You have a style that is unlike anybody else’s. Other people have started to copy it because you were doing the bandage dresses before anybody else. Now everybody’s doing them and you’ve moved on.

WILLIAMS: I’m not given credit. They’ll mention others, but they won’t mention me. Actually, Kelly Ripa mentions me.

LEMON: She watches you.

WILLIAMS: That’s the kind of career I want. You get up, do your show, do a few other things, but mostly you just mind your own business.

LEMON: That’s what people don’t know about you. They think, “Wendy’s out partying. Wendy’s in the streets and in everybody’s business.” But you do your job, and then you go home.

WILLIAMS: Yeah, I’m so glad that I got all of that out of my system. I still like the night club, but that might be a couple of times a year and it’s not a must-do.

LEMON: What are some of the differences between daytime and late-night shows that the average viewer watching at home might not pick up on?

WILLIAMS: The lighting on daytime is way too bright. You have to wear a ton of makeup. At night, the lighting is softer and makes everyone look attractive. And you have a desk. On daytime, nothing’s blocking me. When we first started our show, I wanted a desk, a place to lean my arms while blocking the rest of me. And they said, “No, you must come out. It’s going to be loud and bright.” It was very frightening.

LEMON: Do you think that you get more out of your guests than other hosts?

WILLIAMS: I get more out of my guests than anybody on TV.

LEMON: People underestimate you. They think, “Wendy is a gossipy host.” But you do really great interviews. You have a sneak attack, because you’re nice and you smile. And maybe people think, “Well, this isn’t 60 Minutes.” Then they end up giving you the goods.

WILLIAMS: I’ll never forget the time I interviewed Halle Berry. I was so scared to meet her. When she walked into the room, everyone stopped. She looked directly at me and smiled, and I smiled back. Suddenly, I wasn’t scared. When she sat down, I remembered the list of questions that her publicist and her team said I couldn’t ask her. But suddenly, I felt like, “I’m going to ask her anything I want.” And she said, “Wendy, girl, you can ask me whatever.” And I did. By the end of the conversation, she flicked my boob and winked at me. I didn’t wash that boob for two weeks.

LEMON: You disarm people. You’re like my mom or my auntie.

WILLIAMS: I got all that stuff from my mother and father. I come from a perfect blend of people to make me the way I am.

LEMON: When you transitioned from radio to on-camera, what was the biggest adjustment?

WILLIAMS: Sleeveless dresses. Women all over have a thing about their upper arms. And, Don, I was born a fat girl. Even when you lose weight and feel comfortable with your body, which I do right now, there’s always the fat girl within.

LEMON: How does being on camera every day affect your self-image?

WILLIAMS: Being on camera has affected my self-image in a very positive way, to the point where I don’t even want to talk about it. I am the best mother that I could possibly be. I was the best wife that I could possibly be. I’m definitely the best employee and supervisor and boss that I could possibly be. I’m the best friend that I could possibly be. And I am the best talk show host on all of TV. The others are okay, but there’s only one number-one who happens to not have an Emmy. That’s okay. Awards mean nothing. I feel embarrassingly wonderful about myself.

LEMON: Do you miss being a wife?

WILLIAMS: I do miss being a wife. I feel as though marriage is the highest order of love. I wouldn’t mind getting married again. I would have a very quick prenuptial agreement. What’s yours is yours. What’s mine is mine. I don’t want to be a stepmom and I don’t want to live together. I’ve learned that each of us having our separate place makes it special.

LEMON: Let’s talk about the current media landscape, where everyone has an opinion. Does that force you to be louder?

WILLIAMS: I’m frightened of saying the wrong thing. I was talking with Mike [Esterman, Williams’s companion] earlier. I was sitting on the bed with my legs crossed. When we were children, we called that “Indian style.” I don’t think you could say that anymore. I mean no offense. Mike is Jewish, and always says, “Jew.” And I’m like, “I can’t call you a Jew. It just feels weird.” And I am not African-American. I am Black. I’m tired of all that. If a girl is a whore, I want to call her a whore. But, I guess, you have to say, “She’s fast.” And then a lot of people don’t know what that means. Girl, you’re a whore!

LEMON: Or as we say, “a ho.”

WILLIAMS: The things we used to say, which were a part of regular life, we can no longer say.

LEMON: Are people too sensitive? Everyone talks about “cancel culture,” and I hate those little catchphrases.

WILLIAMS: I don’t even know what cancel culture is, but when you hear Lester Holt talking about it, then you know, “This is way too much. Now Lester’s involved.”

LEMON: People are going back into something someone said 15 years ago and trying to bring them down.

WILLIAMS: It makes me want to rush home after I leave the show, slam the door, lock it, turn on the TV, and see what everyone else is talking about.

LEMON: Wendy, in this business you live or die by the ratings. How do they affect your psychology? Do you obsess over them?

WILLIAMS: When I was with my ex-husband, the ratings would be the first thing I saw every morning. He looked at them when I was taking off my street clothes to get ready for a fitting. He’d put the TV on mute and say, “Wow, you did really good today. This is a reason to celebrate. Do you want to go out for dinner?” And then other days, it’d be really bad. I don’t know any rhyme or reason for the ratings, and I no longer look at them. I just look ahead, do the show, and keep going.

LEMON: Ratings can make you paranoid. It’s like watching Twitter when you’re on the air. It’s not authentic because you start to change things that may not necessarily need changing. Maybe it’s just a bad day. Maybe someone with the ratings book is on vacation. You never know.

WILLIAMS: I know a lot of people who look at ratings obsessively, and that’s just not good.

LEMON: What do you think about celebrity and fame in 2021?

WILLIAMS: It’s easy to get, and hard to keep. I’m not going to overstay my welcome.

LEMON: What do you mean?

WILLIAMS: I want to leave on a high note. I love what I do, but there are other things in life I want to do. I want to go back to the classroom, not as a student, but as a professor. I want to teach in the communications department at some place in New York City. I want to give parents their money’s worth. None of my professors have ever been half of what I’ve become. And I felt it. I want it to be a place where kids love to go. If you’re a communications major, you can ask me anything, and I’ll grade your papers accordingly.

LEMON: But you don’t think that your welcome is on the verge of being run out, do you? I think Wendy’s on a high right now.

WILLIAMS: Don, you and I both know that we could be over tomorrow. You could walk into your studio this evening and have them say, “Here’s your stuff. Your set is packed up.” That’s a fact in this business, and I’m trying my best not to enter that zone. But, I don’t want to do this forever. I want to hop on my broom and fly to Miami and see what’s going on around there.

LEMON: How have your off-air challenges affected your on-air persona?

WILLIAMS: They’ve affected it in a great way. I can’t even hide whatever flaws people think I have. I can’t hide my breasts. I’m not getting a reduction any time soon. Here they are. That’s that. I do not have booty implants, obviously. I have a flat booty. I was born that way. The lymphedema, I can’t hide that. There are my wrinkled, crinkled, discolored feet. I do wear wigs. Listen, I admitted my stuff a long time ago.

LEMON: You’ve been very public about things in your private life—about your marriage, about your divorce, about troubles with your family, about the passing away of your mother. Does that affect your on-air persona?

WILLIAMS: Definitely. When we were married, I was very happy. But I had to make sure that when he and I divorced, my life wouldn’t suffer, because if my life suffered, then that meant my son’s life would suffer, too. I loved Kevin and he loved me, but I was probably too much for him. I guess he found somebody who was just regular and who would cater to his every need. I tried, but hell, I gotta get up in the morning. The idea that the show wasn’t called The Wendy Hunter Show was a big source of problems. If somebody called him Mr. Williams, all of a sudden a sunny day would turn into a storm cloud. I’m disappointed in him, but I quickly got over that because anger causes wrinkles.

LEMON: I always say, “People think Wendy is this exotic creature, but she’s really just a Jersey housewife.” Is that a terrible thing to say?

WILLIAMS: Not only am I a Jersey housewife, but I’m a Jersey housewife who happens to have a job.

LEMON: What’s the biggest difference between on-air Wendy Williams and off-air Wendy Williams?

WILLIAMS: I curse like a sailor off-air. There are a lot of words I use that you’d be shocked by.

LEMON: How do you keep the show relevant?

WILLIAMS: I listen to my staff. I watch a lot of TV. I love magazines. Sometimes I take the long way home and tell the driver to drive slow. I like to look at the people and see what’s going on. What are they eating? What are they wearing? Who are they talking to? Are they paying attention? There’s a part of me that’s 80 years old in terms of some of my hardcore beliefs. But also, I feel like I’m 25 years old.

LEMON: Does Wendy ever get lonely?

WILLIAMS: No. Lonely and alone are two different things. I’m not lonely. When COVID hit, I talked on the phone more than I ever had in my entire life. And that was fun because then I knew who I might want to have sex with.

LEMON: Has Wendy found love?

WILLIAMS: I’m interviewing Mike. He’s not my boyfriend. He’s my special friend. We hold hands and hook arms and eat off each others’ plates.

LEMON: People may be surprised that Wendy’s in an interracial relationship. Should they be?

WILLIAMS: No. I feel very comfortable with him, and he feels very comfortable with me. I’m the first Black girl he’s ever dated, but you wouldn’t guess it. He’s not at all weird like, “Let me feel your hair.”

LEMON: What’s the last thing you think about before you go to bed?

WILLIAMS: Let me sleep restfully and wake up tomorrow.

LEMON: And the first thing when you wake up?

WILLIAMS: Thank god. What hurts?

LEMON: Wendy’s had so many issues. We were worried about her addiction, her health. Should we be worried about Wendy?

WILLIAMS: No, but that’s a fair question because I did have many problems in my 20s with the white. I played that out in my movie where, I think, I fell asleep with a champagne bottle in the bed, and Kevin had me in a sober house. But that was only because the girl he had an affair with was about to have a baby, and he needed to put me someplace where I couldn’t watch TV. He took away my phone. He took away my cash. He took away everything.

LEMON: He didn’t take away everything, Wendy. You’re still here.

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Hair: Jasmine Kelly

Wigs: Nimjaz Hair

Makeup: Merrell Hollis

Set Design: And Or Forever

Production: Perris Cavalier

Photography Assistant: Amina Gingold

Fashion Assistant: Chanel Smith

Special Thanks: Pearl Street Caviar