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At the time they were aired, these interviews seemed light-hearted, possibly even comedic, but looking back now, they feel like chilling warning signs of scandals that would only be revealed years later. But we do begin tonight with singer R. Kelly sentenced to 30 years behind bars after his conviction on racketeering and sex trafficking charges. R. Kelly is spending more time in prison after being sentenced federally for child pornography [music] and enticement of minors. Looking back, some of the warning signs were hiding in plain sight. When R. Kelly was directly asked about his attraction to younger women, his response wasn't a denial. It was hesitation, deflection, and a refusal to give a clear answer. I've been wondering about you. Do you like teenage girls? When you say teenage, how are we talking? Girls who are teenagers. 19? 19 and younger. I have some 19-year-old friends. But I don't like anybody illegal if that's what we're talking about, underage. Uh-huh. I want to show my panel a fascinating interview we found from 1991. Bill Cosby was on CNN promoting a book. He tells an interesting story. Take a look. Over the years, Bill Cosby has faced dozens of misconduct allegations, including accusations involving young victims and claims that he intoxicated them. What makes this clip unsettling is how openly he described behavior that, at the time, was brushed off as normal. Spanish fly was the thing that all boys from age 11 on up to death. [music] We will still be searching for Spanish fly. That's right. And and and what was the old The old story was if you took a little drop No, it was on the head of a pin pin That's right. Drop it in the Coca-Cola. It didn't make it and the girl would drink it and >> She's yours. Hello, America. Our next guest is in his seventh season playing Hyde on the Fox sitcom That '70s Show. Please welcome Danny Masterson. >> [cheering and music] >> In 2023, Danny Masterson was convicted of assaulting two women and sentenced to 30 years to life. After the verdict, an old Conan O'Brien interview resurfaced, and many felt it said everything we needed to know. Like my friend Bodie Elfman, he always teases me and he says, "Hi, my name is Danny Masterson. Would you like to touch my balls?" You know, bad imitation of me because certain words just make it >> people to do that? That's the more important question. Um I've heard about you. Uh And you'll be caught soon. I know you will. >> I will. The case also brought renewed attention to those around him. Ashton Kutcher and Mila Kunis publicly supported Masterson during the trial, a decision that sparked backlash. In response, older clips began circulating again, including moments where inappropriate jokes and comments were made involving young actresses. What is some of the bet you made with Danny about our first kiss? No, it wasn't the first kiss. [laughter] It was like a second or third kiss. >> the first It was like the first week. NO, IT WAS NOT THE FIRST WEEK. THEN DANNY goes and goes, "Dude, I'll give you $10 if you can French kiss her." Why wouldn't you stick my stick your tongue in my mouth or some But no, no, no, no, no. For $10. You're making it sound like it was like really Okay, Dan We had a little side bet, don't we? Another resurfaced clip shows Ashton making a comment about a then 15-year-old Hilary Duff, which drew even more scrutiny. Hilary Duff is in Lizzie McGuire. She also has an album out. She's going to be in a movie called Cheaper by the Dozen, and she's one of the girls that we're all waiting for to turn 18 along with the Olsen twins. During a 2016 appearance on The Tonight Show, Melissa Benoist shared what seemed like an unfortunate injury she had experienced. I was going down steps and I slipped and fell and hit my eye on a potted plant and tore my iris. >> But years later, that story took on a completely different meaning. In 2019, she revealed that she had been a victim of domestic violence and that the explanation she gave on live television was actually a cover for what she was going through privately. I am a survivor of domestic violence or IPV intimate partner violence, which is something I never in my life expected I would say, let alone be broadcasting into the ether. First time it happened, he threw a smoothie at my face. It smacked my cheek and exploded all over the floor and the sofa. I ran to grab paper towels, rushing back because I was so worried about cleaning the couch. Then the fact that it was all over my face, my hair, my clothes, and that my cheek was painful painfully throbbing I just fooled myself into believing I could help him. I thought that I could love him enough to make him see a way of life where violence was not the way you handled emotions. So, I consciously deluded myself into thinking that forgiveness would heal him enough to make it stop. In 2020, Chris D'Elia faced multiple allegations of predatory behavior, including claims involving underage women. After the accusations surfaced, an older podcast clip began circulating, and suddenly a moment that once felt like casual conversation carried a very different weight, where he realized he could be in deep trouble. Yeah, well, that that's weird, yeah. Let me see your body. Let me Dude, if I'm 15 When the topic of Snapchat messages being saved was mentioned, you can see the realization hit almost instantly. The um boy's mother ended up finding it. Finding it? What do you mean? It Snapchat goes [clears throat] away, right? How they He probably saved it. You can screen record, take screenshots. Wow. You got to know that that's going to happen. Some people do some crazy [ __ ] Yeah, he said it says teen's parent reportedly found >> After the proposal's movie launch, Sandra Bullock was making the usual interview rounds until one interviewer shifted the focus to her half-nude scene. The major thing that's changed since you were here last? >> Yes. I have now seen you naked. >> [laughter] >> I have seen you naked. >> about that. >> seen you naked. >> able to sleep afterwards? >> I should tell you you know >> Why are you looking down? >> It's now my screensaver. Why did you look down when you said that? >> at my notes. >> No, your notes are not over here. No, they're right there. Despite her frustration, the reporter circled back and brought it up again. Did I mention you have a nude scene in this movie? >> Pretty much from the time you open your mouth, yeah. Sandra Bullock, come back more often. >> No, not after this interview. >> [laughter] >> Soon after, multiple women came forward with accusations of inappropriate behavior against that same reporter. Just moments ago, NBC News chairman Andy Lack sent the following note to our organization. Dear colleagues, on Monday night, we received a detailed complaint from a colleague about inappropriate sexual behavior in the workplace by Matt Lauer. It represented, after serious review, a clear violation of our company's standards. As a result, we have decided to terminate his employment. While it is the first complaint about his behavior in the over 20 years he has been at NBC News, we were also presented with reason to believe this may not have been an isolated incident. Our highest priority is to create a workplace environment where everyone feels safe and protected and to ensure that any actions that run counter to our core values are met with consequences, no matter who the offender. We are deeply saddened by this turn of events. Katie Couric had already warned us about him, but it was dismissed as nothing more than workplace banter. You co-hosted The Today Show with Matt Lauer for 15 years. What is Matt's most annoying habit? He pinches [music] me on the ass a lot. Wow. I would have a problem with that. Talk shows often rely on pressure to get honest answers, but sometimes that pressure crosses a line, and looking back, this moment between Ellen DeGeneres and Mariah Carey shows exactly what toxic behavior looks like. The other thing is that people are saying that that you're pregnant. There There's rumors >> Don't discuss that. >> [laughter] >> Mariah was clearly hesitant to talk about her personal life, but Ellen pushed the topic further, offering her champagne and suggesting that refusing to drink would confirm she was pregnant. That's not champagne cuz you can't have it. >> is. Is it really? >> Yeah, you want to You want to taste it? I can't believe you did this to me, ELLEN. >> WHAT? NO, I'M trying to I'm not going to ask you if you're pregnant or not. Do you see what Ellen is doing? This is peer pressure. No. Let's toast to you not being pregnant. If you're not pregnant, then Oh my goodness. YEAH. YOU'RE PREGNANT. YOU'RE PREGNANT. IN HINDSIGHT, it's far more uncomfortable, especially knowing Mariah had struggled with infertility. Well, let me take some of the vodka next to me. Why aren't you answering? >> Ellen did that to me and tried to put me on the spot >> All right. with some alcohol. Okay. That's real alcohol. While Hollywood scandals are recent news, within the industry itself, everyone was aware of what was going on. In 2005, Courtney Love was asked a simple question on the red carpet, and her answer immediately stood out. Hi, Connie Chung. Do you have any advice for young girls looking to Hollywood? Um I'll get libel for that. I'm Harvey Weinstein. I invite you to a private party in the Four Seasons penthouse. Years later, she clarified that she wasn't a victim herself, but claimed that speaking out in that moment effectively got her blacklisted from parts of the industry. There are a lot of parents out here who want to put their kids in this in this business. They Their kids are cute. They're great actors. Da da da. What would you say to a parent who just has the best of intentions, who's coming here with their child? >> Corey Feldman was one of the victims of these scandals. Back in 2013, he sat down and warned the public to avoid the industry at all costs. I'm saying that there are people that were the people that did this to both me and Corey that are still working. They're still out there, and they're some of the richest, most powerful people in this business. And they are terrible >> do not want me saying what I'm saying right now. Are Are you saying that they're pedophiles? >> Yes. And that they're still in this business? >> Yes. Nobody Nobody You're legendary for the parties that you throw. You throw a great party. I'm a legend, baby, for a whole bunch of things. >> Yes. HUH? >> [screaming] >> A KILLER PARTY. WHAT'S THE INGREDIENT What is What What do you do to make just an amazing killer party? This is what you need to do. The same pattern extends into the music industry. In recent years, Sean Combs has faced serious allegations, but when revisiting older interviews, some moments stand out in a way they didn't before. Like when he casually described the setup of his private parties during an interview with Conan. Okay. Now, >> [laughter] >> we need um alcohols. Right. >> Alcohols. Right. Not just one alcohol. >> Alcohols. If you don't have what they need, they're going to leave. >> Right. >> Got to keep them there. Right. >> You need You need locks on the doors. >> [laughter] >> Okay, this is sounding kind of dangerous now. It's a little kinky, but you know >> Yeah. Yeah. Rock with me, but just check it out. You need um a lot of heat. A lot of heat. >> Heat? Yeah. >> Heat? You mean that physically the place has to be hot? You don't have no air conditioning. No air conditioning? Why is that? >> Heat affects the alcohol, and it also affects like um you know, everybody gets a little bit more comfortable and loose. Builds up a nice little sweat. That just sounds disgusting. >> What you talking about? [laughter] Depends on the way you look at it. Depends Oh, people start getting kind of gets kind of sexy. Is that what you're saying? >> you sexy. New word for you. Yeah. Uh yeah. Cuz P. Diddy be wanting the body, and you got to tell him no. You got to tell him no. Or the moment a young Justin Bieber began opening up about his experiences, only to be quickly cut off. You got me a Lamborghini. Oh, well, that's nice. >> gotten it yet, though. Yeah, I know. When is that coming, that Lamborghini? We talked about this last time. >> for a day or two. >> And he had access to the house, and he knows better than to be talking about the things that he does with Big Brother Puff on national television. He even predicted his own downfall back in a now archived interview. They won't even give me a permit for the parties, man. They don't want me to throw the parties no more. But we We ain't going to stop. We're going to keep on having fun, bringing people together from all walks of life. You're going to hear about my parties. They're going to be shutting them down. They're going to probably be arresting me, doing all types of crazy things, just cuz we want to have a good time. You know. Hope you enjoyed this video. Let me know which clip you connected with the most.