Top 10 Times Talk Show Hosts Went Too Far

With the pop star Rihanna as his guest, Jimmy Kimmel makes a bold move to share a moment with her. He encourages her to try a challenge in order to promote autism awareness. Reenacting “Lady and the Tramp” with a Twizzler, the two both take an end and make their way to the center. It’s an awkward scene that puts both Rihanna and the host up close and personal. They both laugh it off, but the segment still leaves you with an uneasy feeling. Most viewers would assume that this was all a scheme for Kimmel’s own amusement. The singer does end up mentioning the presenter's wife Molly, perhaps to get some payback of her own by the end.

With legends Jane Foinda and Robert Redford as guests, Megyn Kelly had a great lineup for her show. The segment takes a wrong turn, though, when the host decides to bring up Jane Fonda’s thoughts on aging and plastic surgery. Fonda looks taken aback, trying her best to maintain her composure. It’s up to each viewer to determine just how angry she really is in the moment. The presenter doesn’t seem to realize the shock the question generates, or that it might have struck a nerve. As the guest changes the subject, the controversial exchange moves quickly to thoughts on her latest project.

When Donald Trump appeared on “The Tonight Show,” Jimmy Fallon chose to keep things light. But the host went too far when he decided to mess with the then-candidate’s hair. While Fallon seemed to mean it as a joke, the infamous moment took on a life of its own. It also happened less than a month away from the presidential election. In light of Trump’s controversial candidacy and presidency, the interview took on another context altogether. The comedian’s attempt to turn a politician into a comic character felt like a misstep regardless of your personal beliefs. Even years later, the entire interview comes off as nothing short of cringey.

It wasn’t uncommon for this host to talk his way into uncomfortable subjects. Unafraid to bring up controversies, David Letterman asks Paris Hilton about her time in jail. She tries to answer the host while also looking a little annoyed. Hilton might be a divisive figure, but it’s hard not to feel for her as she discusses her legal troubles. Letterman doesn’t let up as he digs further into one of the low points of the hotel heiress’ life. The presenter plays the segment for comedic effect, but it’s ultimately sad to watch. In interviews after the fact, the guest said that she had an emotional reaction to the event. It’s easy to understand why after watching the clip.

In 2008, Mariah Carey joined “The Ellen DeGeneres Show” to chat about her life and career. The conversation soon turns to the topic of her potential pregnancy. The singer plays it coy, but the host pushes the guest for an answer. This includes toying with Carey by offering her champagne. The artist kindly pushes back, likening the treatment to peer pressure. DeGeneres pours a glass and makes a toast as the vocalist tries to get out of it. It all leads up to the comedian wanting to make the big announcement, not stopping to think about her guest’s state of mind. Carey later spoke ill of the interview and we don’t blame her for it.

Working through her own personal demons, Lindsay Lohan still chose to go on David Letterman’s show. The comedian doesn’t waste much time in bringing up the actress’ past. Pressing her about rehab, Letterman wants to know the details that aren’t as easy to talk about. Lohan tries to play along even though she appears to be less than enthused. With continued questions about substance use, the guest endures a storm of jokes at her expense. The presenter tries to bring it all back around with some encouraging words that seem too little and too late. Lohan has a sense of humor about her mistakes, but the interviewer can’t seem to stop.

To promote their film “The Birdcage,” Nathan Lane and Robin Williams appeared on “The Oprah Winfrey Show.” The host questioned Lane about his role and his sexuality. It was a rather forward way of discussing the subject, especially considering that it was a different cultural landscape in the 90s. Before the actor could answer, his co-star popped in to divert attention away. Lane later recalled that Williams saved him from having to reveal anything to Winfrey. It was definitely too forward to ask about the guest’s sexual orientation, only putting the interviewee into a difficult position. The performer said that he was not ready to discuss the topic at that time and thankfully there was someone there to help.

When Judith Light arrived on “The Tonight Show,” she demonstrated how a particular outfit could be taken off for filming purposes. This segment included an eager Jay Leno wrapping his arms around the actress. Despite her uneasiness, the host stayed in close proximity and made a few jokes at her expense. It’s definitely awkward and more than a little gross to watch Leno manhandle her. This is especially true when Light asks to cut away, with the comedian continuing his questionable behavior. And guest Chris Farley’s antics only make it worse. It’s hard to imagine this sort of segment flying on any current talk show.

While a guest host on the popular ABC show “The View,” Kelly Osbourne chose to speak out against Donald Trump. Her choice of words weren’t exactly the best. In response to the politician’s immigration stance, the presenter chose to make a controversial statement about Latinos. The reaction from her co-hosts says it all. While Osbourne tries to walk it back, the damage is immediately done. There’s a lesson to be learned here about knowing what to say and when to say it. She might’ve been trying to make a point, but it ends up being drowned in offensive and insensitive language.

No stranger to controversy, Bill Maher finds himself in hot water on a semi-frequent basis. This includes when he chose to use a racial slur on “Real Time.” Maher was interviewing Senator Ben Sasse at the time, using the insensitive phrase in response to the Nebraska politician’s mention of working in the fields. The media backlash followed soon with the comedian offering up an apology. Regardless of the context, the host stepped over the line when he decided to say what he said. He also received direct criticism on his show by the likes of Ice Cube.

Did we forget another memorable time talk show hosts went too far? Let us know in the comments below.