- 21 hours ago
These interviews will make you cringe harder than a root canal... Join us as we count down our picks for the most uncomfortable and unsettling late night talk show moments! Our countdown includes Madonna dropping f-bombs, Letterman making celebrities cry, inappropriate touching, and hosts crossing lines that should never have been crossed.
Category
🗞
NewsTranscript
00:00Welcome to WatchMojo and today we're looking at the most uncomfortable and unsettling interviews
00:08on late-night talk shows. For this list, we're not including performance bits that were intentionally
00:13weird. Megan Fox on Jimmy Kimmel Live. Our first guest is maybe the most appropriately named human
00:26on the planet. You can see her now fighting robots from outer space in the number one movie in the
00:31galaxy, Transformers Revenge of the Fallen. It is in theaters now. Please say hello to Megan Fox.
00:36While promoting her 2009 film, Transformers Revenge of the Fallen, Megan Fox shared a vulnerable moment
00:41with Jimmy Kimmel. She mentioned the first time she worked with Transformers director Michael Bay.
00:46The first time I ever worked with him actually, I had just turned 15 and I was an extra in Bad Boys 2.
00:53She was only 15 years old, yet she was dressed in a bikini and six-inch heels. To make matters more
00:58suggestive, she was made to dance under a waterfall. Kimmel showed absolutely no sympathy for her
01:03uncomfortable and inappropriate experience. He laughed and wrote off Bay's behavior as normal.
01:09She's 15, so you can't sit her at the bar and she can't have a drink in her hand. So his solution to
01:14that problem was to then have me dancing underneath a waterfall getting soaking wet. And that's...
01:21Perfectly wholesome? At 15, I was in 10th grade, so that's sort of a microcosm of how Bay's mind
01:27works. Yeah, well, yeah. Well, that's really a microcosm of how all our minds work.
01:32But is it really acceptable to put a child in those conditions? Ryan Phillippe on The Tonight Show
01:36with Jay Leno. But sometimes I'll have these flashbacks when there's a push-in. It feels like
01:40the soap opera. Actor Ryan Phillippe's breakthrough role was the character Billy Douglas on the soap opera
01:45One Life to Live. Billy broke ground as the first openly gay teenage character on TV. Keep in mind,
01:52this role was acted from 1992 to 1993, at the height of the AIDS crisis. Fast forward to 2008,
01:58when Phillippe promotes his new movie, Stop Loss on Jay Leno. The talk show host seemingly couldn't
02:03leave the past behind or get over his own apparent homophobia.
02:06Like, say that camera was your gay lover, number two. Wait a second. He pressured Phillippe to give
02:12the camera his gayest look and wouldn't back off despite the actor's resistance and threats to
02:17walk off the set. After being called out by GLAAD, playwright Jeff Witte, and others,
02:21Leno apologized and said it was a dumb joke.
02:24Can you give me your gayest look? Right. Say that camera. Say that camera. I will not. Say that camera
02:29is Billy Bob. Billy Bob has just ridden in shirtless from Wyoming. Wow. That is so something I
02:34don't want to do. Madonna on The Late Show with David Letterman. This infamous interview was
02:39uncomfortable for both Madonna and Letterman. While the guest had nothing in particular to promote,
02:44she did have a reason to seek revenge. Let's go kiss the guy in the audience. Why don't you go kiss
02:48the guy in the audience? Why are you so obsessed with my sex life? As we all know, I have none of my own.
02:54Letterman had been dragging Madonna in his nightly monologues, and it was time for her to get some
02:58payback. She began the interview by asking a salacious question. She dropped the F-word 14 times.
03:03She insulted Letterman's hair, and said he'd lost his edge since becoming successful.
03:08The host was visibly unsettled at points.
03:10You can't get through a show without talking about me, or thinking about me.
03:16But he wasn't free of blame either. He repeatedly insisted that Madonna kiss an audience member,
03:22despite her repeated refusals.
03:24Help!
03:26Who said that?
03:27No, no, that's the guy you wouldn't kiss earlier.
03:29The tense interview ended up being one of the most censored talk show appearances in TV history.
03:35Kanye West on Jimmy Kimmel Live.
03:37Kanye West is one of the most controversial musicians in recent years.
03:41Do you feel like your attitude towards women has changed since having daughters?
03:49Nah, I still look at Pornhub.
03:50From his support of Donald Trump, to his anti-Semitic tendencies, he's found himself in hot water
03:55many times. In 2018, he appeared for an interview on Jimmy Kimmel Live, and it didn't go smoothly.
04:01West gave rambling answers to most of Kimmel's questions.
04:04Everyone's not thinking sometimes.
04:07Galileo, they want to chop his head off for saying that the earth, that, what do you say,
04:13the sun revolved around the earth, and vice versa.
04:17He also compared himself to famous people like Walt Disney, brilliant minds like Leonardo
04:22da Vinci, and even religious figures like Jesus. But he was curiously silent on one topic.
04:27When asked why he supported Trump, the rapper paused for so long that Kimmel jumped for a
04:32commercial break.
04:33You so famously and so powerfully said, George Bush doesn't care about black people. It makes me wonder
04:39what makes you think that Donald Trump does, or any people at all.
04:48Why don't we take a break? We'll come back.
04:50Paris Hilton on The Late Show with David Letterman
04:52Paris Hilton was in jail for a brief period in 2007, but that wasn't the reason for her visit
04:57to The Late Show. She was actually on the program to promote her perfume and business ventures.
05:02She was assured that Letterman would not bring up her jail time in the interview,
05:05but he quickly broke that promise.
05:07How have you been? Are you all right?
05:08Good. Good to be back in New York.
05:10Yeah, good to have you. How much time do you spend in New York City? A lot?
05:13Not as often as I'd like.
05:14Which do you prefer, New York City or Los Angeles?
05:16I like both. I like the weather in L.A. better, but I love New York City.
05:20New York City is exciting, though, isn't it?
05:21I was born here, yeah.
05:22Yeah, good for you. How'd you like being in jail?
05:25Not even a minute after she sat down, the host began to grill her on being locked up.
05:29Despite Hilton's visible discomfort and terse answers, Letterman did not let up.
05:34I guess the food was just awful, wasn't it?
05:36Yes. It's not supposed to be good, it's jail.
05:39Did you have three meals a day?
05:41Hilton later said in a 2021 podcast episode that she believes he intentionally tried to
05:46humiliate her. Letterman later apologized privately and publicly, but his cruel sense
05:50of humor certainly left a mark.
05:52Yes. I, you know, when I went in there, I had my team talk with him and make sure that
05:59he would not ask me anything about it.
06:01Wow.
06:02So there was not supposed to be one question, and then he just kept pushing me and pushing
06:05me, and I was just getting so uncomfortable and I was so upset.
06:10Donald Trump on The Tonight Show, starring Jimmy Fallon.
06:12You feel like you're off the cuff, you get yourself in a lot of trouble sometimes. I
06:15think you dig yourself a hole sometimes, a deep hole, and then instead of getting out
06:19of the hole, you just dig deeper.
06:21Before he was elected president the first time, Donald Trump appeared on The Tonight
06:24Show starring Jimmy Fallon in September 2016.
06:27Many people expected and wanted Fallon to ask the already controversial Trump hard questions.
06:33However, they got a playful interaction instead.
06:36Fallon skirted tough questions and sensitive topics, opting for jokes and games.
06:40He also tousled Trump's hair, which was way too friendly for some viewers.
06:44Can I mess your hair up?
06:48With Night Harris.
06:55In 2018, Fallon said he would have done the interview differently so as not to normalize
06:59the guest's political beliefs or behavior.
07:02Trump, of course, snapped at the host and told him to be a man without regret.
07:06If I'm losing or lagging, I'd never mention him.
07:09Lindsay Lohan on The Late Show with David Letterman
07:12She intended to promote her new film, Scary Movie 5, but Letterman decided to grill Lindsay
07:17Lohan on rehab and legal troubles.
07:20Some of the activities are not true at all, is that right?
07:23Yeah.
07:23Yeah.
07:26He was egged on by the audience and undeterred by Lohan's clear discomfort.
07:31She took the ribbing with good humor, continuously cracking jokes, but there came a point when
07:35it was just too much.
07:37Now, aren't you supposed to be in rehab now?
07:42Do not watch anything that goes on.
07:44I do.
07:44Are you a tabloid now?
07:45Now, here's what I...
07:45May 2nd.
07:46I was under the...
07:47May 2nd.
07:48She tried avoiding questions.
07:49She tried cutting him off.
07:51But Letterman kept pestering her about rehab until she began crying.
07:55As the interview goes on, Lohan tries to hide her tears until the host hands her a tissue.
08:00It's not in good taste to make your guests cry in the first place, and even worse, to
08:03draw attention to it.
08:05You can't make a joke of it.
08:06I just want to...
08:07I just...
08:07That's so mean.
08:08I don't...
08:08I'm not joking.
08:08No, you're not doing that.
08:09We're not doing that.
08:10Abel Ferreira on Late Night with Conan O'Brien.
08:13Bad-mouthing guests who have been on your talk show is never a good idea.
08:16It makes for awkward follow-ups, not to mention, it's just rude.
08:20However, Conan O'Brien broke this rule in 2018.
08:24He was on Dax Shepard's Armchair Expert podcast and named the worst guests he ever interviewed.
08:29Director Abel Ferreira.
08:31Ferreira was supposed to promote his 1996 movie, The Funeral, but he was obviously disinterested
08:35in answering any questions.
08:37I heard that she wanted...
08:38She kept wanting me to beat up Keitel.
08:40That was her thing.
08:42She said, if you're any kind of director, you'd beat him up.
08:44I said, beat him up.
08:45That's my way of being a director.
08:47Yeah.
08:48Beat him up.
08:49You're going to beat him up?
08:50I said, maybe tomorrow.
08:52Why did she want you to beat up Harvey Keitel?
08:55You tell me why.
08:57Okay.
08:58Here's the story.
08:59According to O'Brien, Ferreira ran out of the building before they went on air.
09:03He was dragged back inside and forced to sit for the segment against his will.
09:07Understandably, this added to his bad mood, an uncomfortable demeanor.
09:11So we'll start off nude.
09:12Uh-huh.
09:13Work our way into a...
09:19What's she doing?
09:19Watch out.
09:21It's just me.
09:21Is it just me?
09:23Jennifer Aniston on The Late Show with David Letterman.
09:25The landmark TV show Friends was still widely popular when Jennifer Aniston went on Letterman.
09:31Early in the interview, he repeatedly asked uncomfortable, objectifying questions about
09:35a recent experience in a steam room.
09:37But that's not funny anymore.
09:38No, it's fine.
09:39What'd they do?
09:41They asked her for who you are, and then, you know, and I go, yeah, all of me.
09:45And then, you know, they asked, then somehow they whipped the camera out, and I don't know where the hell they were.
09:49They got a camera.
09:52They have a camera in the steam room.
09:55That's odd, ain't it?
09:56These aren't the kind of moments you actually want to share with everyone, are they?
09:59These are things you just keep to yourself.
10:01You seem like a very nice young woman.
10:02Then, with no segue whatsoever, he asked to try something.
10:06He puts a lock of Aniston's hair in his mouth.
10:08Forgive me if this is rude, I just want to try one thing.
10:11Okay.
10:11Anton.
10:15What are you doing?
10:21What are you doing?
10:22Despite squeals of discomfort, moving away, and obvious confusion, he continues sucking on her hair.
10:30It was clearly a planned bit, considering the musical cues and napkin at the ready.
10:35But Aniston was also clearly unaware.
10:37Still, the audience laughed and applauded this gross behavior.
10:40That was something that I'll never forget.
10:42Before we continue, be sure to subscribe to our channel and ring the bell to get notified about our latest videos.
10:48You have the option to be notified for occasional videos or all of them.
10:52If you're on your phone, make sure you go into your settings and switch on notifications.
10:58Andy Dick and Ivanka Trump on Jimmy Kimmel Live.
11:01Comedian Andy Dick is no stranger to controversy, upsetting humor, and inappropriate conduct.
11:06In an unusual appearance on Jimmy Kimmel Live in 2007, he sat with businesswoman Ivanka Trump.
11:12I have no idea what he's doing behind me.
11:14However, he took this as an invitation to do quite a lot more than sitting.
11:18He displayed a complete disregard for personal boundaries when he began stroking Trump's leg while she was speaking.
11:25Andy, don't please.
11:27Don't touch Ivanka.
11:29Oh wait, did I say I was single?
11:30I meant I had a voice.
11:32Andy, please.
11:34Donald Trump will kill both of us.
11:36She tried to diffuse the situation with humor, and Kimmel quickly intervened.
11:40But that wasn't enough.
11:41He continued touching her legs and hair.
11:43Security soon had to show up and drag Dick off the set.
11:46Andy, you promised you would behave yourself.
11:49I know, I know.
11:49What disturbing moments from late night interviews live rent-free in your head?
11:53Let us know in the comments.
11:54Min turn the audio.
11:55We'll have a look at this.
11:55Let us know in the comments.
11:55Many comments.
11:57Thanks.
11:57We will be right back.
11:59Eat your face with wind-free.
12:01He winszeichcom.
12:02One off this off this stand.
12:02Over it, come back to my back.
12:03There we go.
12:04ho chakra 3, console 3, console 9, 1, 1, 2, 1, 1, 1.
Comments