The 10 Biggest Bombshells From Wendy Williams’ Documentary What a Mess!

While all of Wendy Williams: What a Mess! is well worth your time, here are the 10 biggest bombshells that you need to know now.

“Weight has always been a big deal to me, and that seed was planted growing up,” Wendy Williams admitted early in her Lifetime documentary, Wendy Williams: What a Mess! “I remember my first diet in first grade: tuna fish and mustard in a plastic container, a few grapes on the side. That’s it. I’d have to take the money off my father’s dresser, the change, and I would eat the school lunch. I’d eat the tuna fish and mustard, pull out my change, have an ice cream sandwich, chocolate milk, the whole bit. My father, the first man who loves you. The first message about my weight is, ‘Wendy, you have such a pretty face. If you just lose some weight…’ I would get weighed constantly by my mother and father.”

The prodding about her weight led to a bout of bulimia that she only stopped when she read about a Hollywood actress’ teeth rotting in a tabloid. “I’m a tooth-anista and I said, ‘OK, this is not the way to go.'”

After learning about the possibility of body modification in the tabloids shortly after kicking bulimia, Wendy said she became committed to liposuction and a breast enlargement as a way of sticking it to everyone who’d had something to say about her weight. By 1994, her radio career had allowed her to save up enough money for her procedures. “The doctor said, ‘You know, Wendy, it’s gonna take two sessions. So we’ll do your breast implants and the first part of liposuction first.’ And I’d gotten from above the boobs down to my knees. ‘And then the second session, we’ll do the rest of the liposuction you want.’ And I paid in cash. Not a credit card…Liposuction is a luxury.”

“Early in my radio career, there was this artist. And he had the No. 1 song on the R&B charts at the time. He came and did an interview on my radio show and he asked me out for dinner. So I say, ‘Yeah,'” Wendy revealed. The night quickly took a turn, however. “He wanted to go change for his own party. When we went to his hotel, he invited me to his room and I went. He goes in the bathroom to do whatever. When he comes out, he’s got, like, nothing on. A pair of boxers. And I’m like, ‘OK, what’s about to happen?’ My dumb behind, instead of just getting up and walking out, I’m like, OK, I’m going to see how far this is going to go. I don’t want to have the sex. I don’t want want to be involved with an artist. He ended up pushing himself on me, and he date raped me. And I left after that, went home and scrubbed my skin off, cried. That was that. I never told anybody. I just handled it.”

When asked by a producer off-camera why she hasn’t ever named her attacker, Wendy responded, “It’s my story to tell. I know I can say his name, but, you know what, I’ll let him breathe. Because he was a one-hit wonder. Thank God I am not dead or diseased, you know? If anything it made me more focused and determined to move on with my life.”

If you’ve ever heard the rumor about a Wendy Williams-Notorious B.I.G. hook-up, Wendy has set the record straight. “You’ve been wildly curious about it for years. Now I’m telling you. Big was one of the rappers that was never scared to come see me. We just had a cool relationship. He’s the hit with the music, and I was the hit on the radio,” she said about the late Christopher Wallace. “I liked him. He had a great sense of humor, and he liked to eat. One day, after we did an interview, Big asked me out. I said yeah. I wasn’t thinking about Big in a romantic way. I mean, he was a nice guy, but definitely not my type. But I was still very single and, you know, a young girl. And I was out here, doing it.”

For her, the night out was nothing more than a shrewd opportunity. “I wanted to go to the Shark Bar. The Shark Bar was a scene at that time, and I planned this scene,” Wendy admitted. “I said, ‘Let me get on Page Six. It’s good for my business.'” She held his hand “just to create a stir” and they were seated at a table in the middle of the restaurant. “I mean, it was the best thing for my business ever,” she added. However, the night solidified for her the idea that she didn’t want proximity to celebrity culture quite in that way. As she summed it up, “It was a nothing night.”

Willing to take on any role in the radio world at the start meant some odd hours for Wendy. “I did overnights, which is the worst time on any radio station. It became, alright, you gotta stay up. So I started doing a lot of coke,” she admitted of the start of her substance abuse issues. “I mean, not a lot at times. Like a pile of Peru, that wasn’t me. But I got high, like, five days a week. I did it for years. It was no big deal. And ‘no big deal’ became a big deal.”

The cocaine use quickly became dangerous. “There was one particular night where I go to the bathroom, standing in the mirror, take my hit, pass all the way out down to the ground. My head hit the wall and I woke up,” Wendy recalled. “There was nobody at the station. I could’ve been dead. It’s a miracle I’m sitting here now, actually. And then Kevin came along.”

It was future ex-husband Kevin Hunter, whom she met at a skating rink in April 1994, that she credits with getting clean at that time.

While Wendy’s sharp tongue hasn’t always endeared her to everyone she talks about, one time it wound up putting her in some potential danger. “I remember one time I said something about Puffy‘s R&B group Total on the radio. I guess they didn’t like it, he didn’t like it,” she recalled. “Most people don’t like it, but they’re very entertained. I respect your hustle, why don’t you respect mine?” Instead of respect it, the ladies of the group showed up at the radio station intending to fight. “As soon as I opened the door, there’s a van outside. Keisha, Kima and Pam from Total jump out—boom—hit the sidewalk and try to rush me. They were going to kick my ass.” As if on cue, though, Kevin pulled up in their car and rushed Wendy out of the scene. 

Wendy’s first pregnancy came when she was working at Power 99 in Philadelphia, doing long-distance with Kevin in New York City. After she miscarried at five months, Kevin decided he wanted to marry her. They didn’t tell her family until after they’d made it official in November 1997. A second pregnancy followed shortly thereafter, with the same tragic result as her first. “The entire city saw me have two five-month miscarriages,” Wendy tearfully recalled. “I was out doing public appearances with a burgeoning belly, and I had to deliver the babies with the epidural and the ‘push, push, push.’ And the nurses, they said, ‘Do you want to know if it’s a boy or a girl?’ I said, ‘No!’ ‘Do you want a funeral?’ I said, ‘Just go.'”

Feeling as though she was being punished by God, Wendy considered ending her marriage, thinking she wasn’t “woman enough” to give Kevin a child. But they successfully welcomed Kevin Jr. into the world in 2000, after Wendy insisted that she work from her bed throughout the pregnancy.

Two months after giving birth to Kevin Jr. was when Wendy first caught Kevin in some suspicious behavior, talking on the phone with another woman in the middle of the night. She chose to forgive the incident as a mistake, as Kevin further isolated her from the people in her circle while keeping an apartment of his own. Years later, after the talk show was up and running, she’d begun hearing “buzzings and rumblings.” So she eventually hired a private investigator to follow Kevin “low and slow.” Eventually, photos of Kevin in Miami with “the girl” turned up when he was supposed to be in Los Angles for business.

Former co-host Charlamagne tha God admitted that it was he who introduced Kevin to “the girl,” Sharina Hudson. “I didn’t introduce them like, ‘This my dude, you should hook up.’ It was like, ‘Yo, she’s trying to be a model. You’ve got your modeling agency. This is somebody you should connect with.’ They ended up connecting a little too much.”

When Wendy found out that Kevin had purchased a house to share with Sharina only nine miles away from her own, she went to check the property out. “I was cupping my eyes in every window,” she recalled, thinking it was good “come up” for the 32-year-old woman who’d been with her husband for a decade. And then she got a little bit of revenge. “I pulled out my spray paint and I spray-painted ‘Kevin and Wendy Forever.’ And to this day, it still is forever. Doesn’t mean I love you, not like that. Love don’t live here anymore,” Wendy said. “And I had my Gorilla Glue, which is fabulous, and I glued the mailbox closed…and I spray-painted pink all over it. I’m just crying and having a good old time in my own head, saying, ‘Alright, Wendy, you’ve always been strong. Girl, this is your time. You’ve got to get this mess together.'”

She wouldn’t file for divorce until 2019, when she learned that Kevin had gotten Sharina pregnant. 

When Wendy announced live on air in March 2019 that she had been residing in a sober living house for months, her audience wasn’t alone in their surprise. The Wendy Williams Show executive producer Suzanne Bass admitted that she found out at the same time. “I didn’t know,” she added. “It blew my mind…I honestly had no clue. I thought she was coming in from Jersey and going to the studio. That’s what I thought. I had no clue she was leaving in her car and going to Queens after the show. Afterwards, I gave her a hug and I said, ‘Good for you. Good for you for doing this.'”