Most Disturbing Moments as Wendy Williams Opens Up in Painful Docuseries

It's not a pretty picture painted by the docuseries that started with a whole different goal. Spread across two nights and more than four hours, the series was intended to tell the story of Wendy's big comeback as she prepared to launch a podcast.

Instead, producers got a much darker and sadder story. They paired the footage they got with Wendy and her management team in New York, struggling to try and forge ahead with this comeback vehicle amid increasingly alarming behaviors, with interviews with various members of her family, concerned about her well-being.

By the end of this night, it was hard to know what to think about all these different people. Her manager Will Selby certainly appeared to have her best interests at heart, pouring out alcohol that he finds in her apartment and trying to get her to take care of herself.

Her drive, Jammail Nesfield, expresses his concerns about memory loss and the dramatic changes in her behavior -- in particular, her temperament gets much darker as the series progresses -- but her publicist seems oblivious to any erratic behavior.

Then, there's her family who are concerned that the only "friends" she has in New York are people who are getting paid to be around her. Meanwhile, they've basically been cut off from any and all contact with her, including her son.

In fact, the last time he'd seen his mother was when he filmed a viral video with her in Florida, where she appeared to be enjoying improved health and, according to her son, improved cognitive awareness and recall.

Then, she wound up back in New York for the infamous Wells Fargo court appearance that resulted in her being put under a financial guardianship -- and because of concerns of financial malfeasance by Kevin in particular, that guardian was a third party, and not family.

When asked if he thought his mother needed a guardian, Kevin shot back, "I think that my mother should have family. The family's side of the story hasn't been told so it's kind of left this gray space of who's telling the truth and what's really going on."

"I feel like the situation she's in right now isn't really the best situation for her journey of trying to heal," he said of Wendy up in New York without any friends.

This is echoed at a dinner scene with Will and Keesha from her management team. "I wanna have friends," she laments to them. "Guys and girls. I have no friends, you know what I mean? I know nobody."

They tried to argue that she's beloved and adored, but she pushed back that that's not friendship.

As for why Wendy is disconnected with the family, Kevin thinks it comes down to one thing: alcohol. According to her nephew Travis, it was Wendy's decision to cut him out of her life when she had to go to court over her finances.

"When she walked in the court, she requested liquor and a walker. And when they looked at her, they said, 'Do you want Kevin here or do you want Kevin to leave?'" Travis said. "And she was like, 'I want Kevin gone,' because that was the person who was stopping her from Whoppers and liquor."

Now, Kevin worries that having them out of her life is only exacerbating her issues. "Unfortunately, when she's in New York she doesn't have anybody to really call on to wanna do anything with her unless they're getting paid," he laments. "I think that once she realizes that, that's when the lonely feeling sets in. That's when self-sabotage occurs."

Producers didn't hesitate to ask Kevin about reports that he'd been overspending, with his cousin Travis Finnie also weighing in. "There's a lot of blogs that come out, and the accusation was made that the entire family is trying to steal her money," he said.

As for Kevin, the docuseries alludes to him being the main factor in Wells Fargo's decision to freeze Wendy's account. When she was in Florida, Kevin was her power of attorney, and then it was Kevin who was seen as over-spending his mother's money.

"When my mom was living down here, as one can imagine, it's not a cheap lifestyle," Kevin told the docuseries crew. "The court tried to frame it as though I was making all these charges for my own happiness and stuff."

"My mom has never been a cheap person, so whether it be flying her back and forth on private planes or even paying for appointments, it was all under one American Express," he continued.

Travis weighed in as well, bringing some actual numbers into the conversation. "I think the amount of money they questioned Kevin about spending was, like, $100,000," he noted. "To put it in perspective, Kevin's birthday party that year that his mom threw was $120,000. Kevin's rent was $80,000. Kevin's Uber Eats probably exceeded $100,000, that his mom approved."

"So for them to have a court case and rip him away from taking care of his mother, it's very questionable," he concluded. As for Kevin, when pressed if he'd ever taken money from Wendy's account, he insisted, "Not without her consent.

Speaking to the family's concerns that those around Wendy in New York aren't truly there just to be her friend, but rather because they're getting paid, there's certainly a mixed reaction to how her manager Will interacts.

He's often seen confronting Wendy about her alcoholism, with him saying that he combs through her apartment every day to find bottles and pours them out. But there's also a professional incentive to keep her sober and coherent, as there is a project he's trying to move forward.

"I don't know how much alcohol she consumes, but I threw the damned liquor away," Will said. "I don't know if it's gonna stop her … I never feel powerless, but I do feel like I just need help. Because I don't think I can do this alone. I would be lying if I said I think I can conquer alcoholism alone."

Even as Wendy's behavior grows increasingly erratic, her management team continues to forge ahead. Part of it, viewers are told, is just the normal Wendy behavior. She's always been brash and in your face and a little bit condescending and rude to people.

"She's going to get the help that she needs because she's trying to make a powerful comeback," Will explains. "That's what I'm here for. To make sure that she's representing correctly and I clean everything up and we see the Wendy that we've grown to love."

At one point, talking about this podcast, Will tells the producers, "I feel like the podcast is the heartbeat of everything that we're trying to do for Wendy. I feel like Wendy wants to connect with her fans in a different way."

They ask him if he thinks she's ready to do a podcast, but he turns it around on them. "n regards to her being ready, let me ask you. You was with her for two, three days, do you think Wendy's ready to do a podcast?"

Apparently, the producers shook their heads, because though they said nothing audibly, Will called them out on that, asking them why they question her abilities. "She does this in her sleep. So that's why I don't understand where the doubt comes from," he argues.

The producers expressed that doubt while talking with Wendy's niece Alex. "We've spent a lot of time with her," the said. "We are concerned."

It was after the premiere night's most harrowing scene that her publicist Shawn appears to be even more obtuse about what's really going on. When asked if she's worried, she made it clear she has no concerns at all, saying, "I feel that she really knows how to control herself."

"As long as she has people around who are 'yes' people, the same thing is always going to occur where she will ultimately find any excuse to be by herself so she can get back to drinking," said her son.

Hinted at in the trailer, the vape-shopping sequence is even more uncomfortable and difficult to watch in its entirety. In it, her driver Jammail and publicist Shawn are taking her past the old studio of her show and to a nearby smoke shop to pick up a new Blu vape pen.

However, when they arrive at the shop, she immediately shouts that it's not right. "This doesn't look like anything familiar when I'm going to The Wendy Williams Show," she insists. They try to tell her this is the same place but she won't hear it, shouting at Shawn to return the vape pen she purchases and ultimately to drive past.

Jammail then goes back around and passes the site of her old show, pointing it out to her, and pulls up to the same place. As he does, she insists they needed to go by the show's building ... which they had just done. All the while she is berating and shouting at both of them relentlessly.

"I have no idea where we are," she finally admits, sitting in front of the same smoke shop that she'd been going to for years, just down from the site of The Wendy Williams Show.

Afterward, when the documentary crew asks Jammail -- who said he'd been with Wendy about a year at this point -- his thoughts about that night, he expressed some real concern.

"From when I first met Wendy, she had a beautiful personality. Now, it's just like, I don't know what the hell is going on," he said. "I don't know what she's going through, but it's getting very intense, whatever she's going through."

"I think she's losing memory. Have you guys noticed that?" he asks the crew. "Like, you talk to her and she just blanks out. Sometimes, she doesn't even realize who I am. I've picked her up many times, she's like, 'Hey, who are you again?' Dealing with someone like that is very hard On a daily basis to be around Wendy, that needs to be a super-paycheck."

Evident from the beginning was that this Wendy Williams was very short-tempered, short with her words, and seemed ready to snap at a moment's notice. She also was prone to quick tears and dramatic mood shifts, as if her emotions were barely under control.

But the most dominant facet of her personality that grew more and more dominant was her quickness to anger. She started snapping at everyone in a way that her family even conceded was more than usual.

"Ma has tougher skin than most people," said Kevin. "So she does expect other people to have tough skin. But I remember ten years ago, it was clearly something going on. The changes started and it's progressed. At this point, I think it's just hit a head."

As for those enduring it day by day, Shawn said that she has "very thick skin," so she just shrugged off things like Wendy telling her she needed liposuction, or dismissing her by telling her to "go downstairs and order something to make you fatter."

Wendy even snapped at the docuseries crew, demanding one producer leave for asking her if she supports her son financially. Interestingly, though it could be that she just didn't fully process or understand the question, Wendy refused to answer when a producer said, "I think some people worry about you and them losing you. Do you understand how much people love you that way?"

"Next question please."

"Wendy being pissed off is normal," Will said at one point. "She doesn't' really mean it. She's a pain in the ass … She may like you today and not like you tomorrow."

There are scenes that involve her snapping at her physical trainer for wanting her to do exercises that would have her stepping up. She reveals how her lymphedema has affected her feet, which definitely do not look well, revealing that she only has 6 percent sensation in them.

She snapped in a lot of her answers to documentary questions, while at other times, she offered inconclusive or one-word answers, with Will jumping in to help her finish her thoughts. He was definitely on hand to help her when they visited her hometown of Asbury Park for a photo shoot. There, Wendy proved she could still turn it on, but also struggled to remember where the house she'd grown up was.

The night ended with the documentary crew arriving to find her slurring her words and looking much the worse for wear after several days off from shooting, she then slipped into a deep sleep, at which point they called her management team.

After Will gives her some tough love and tells her to get up, she snaps at him, throwing him out of her room, and then lamenting to the cameras about what she has to deal with. Will come back in and asks her why she's whispering to the cameras.

"Because these are my friends. Not you," Wendy replied.

When asked again about concerns regarding her mental state and alcoholism and how much she might be drinking, Will admitted, "I probably just don't ask because I don't want to know."

This first night told the story of how Wendy always wanted to be famous as she tried to build toward her big comeback. By the end, it was clear that she had much bigger issues, with the documentary crew even expressing their concerns about her well-being.

That moment at the smoke shop paired with the state she was found in at home appeared to mark a turning point in the intentions of the docuseries as concerns about Wendy's state begin to take center stage.

Where Is Wendy Williams? wraps up Sunday at 8pm ET on Lifetime.