These awkward celebrity interviews will make you cringe. Welcome to WatchMojo, and today we’ll be looking at moments in celebrity sit-downs that have been most awkwardly twisted by changing views in society or revelations about the interviewer or interviewee.
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00:00 You have a top ten list I'm told.
00:02 Yeah, I'm sitting on it.
00:03 You're sitting on it? Oh, are we going to do the list?
00:05 Welcome to WatchMojo.
00:07 And today, we'll be looking at moments in celebrity sit-downs
00:11 that have been most awkwardly twisted by changing views in society
00:14 or revelations about the interviewer or interviewee.
00:18 I think that sexuality is something that each individual should deal with in their own way.
00:24 Number 10, Jennifer Aniston, Late Show with David Letterman.
00:29 People today can barely grasp the pop culture phenomenon that was Jennifer Aniston's hair.
00:36 During her 1998 Late Show appearance to promote the object of my affection,
00:40 David Letterman went too far with the object of fans' affection.
00:44 He broke a moment of silence in the conversation to say,
00:47 "Forgive me if this is rude, I just want to try one thing."
00:50 He then pulled the length of Aniston's hair into his mouth.
00:53 It was a jarring style with a beauty icon's signature 'do'.
00:57 The gag was brushed off for years until Letterman's notoriously mean-spirited interview with Lindsay Lohan in 2013.
01:04 Is he supposed to be in rehab now?
01:06 Or not watch anything that goes on?
01:09 The incident with Aniston is now seen as indicative of Letterman's unsettling treatment of women.
01:14 Aniston didn't seem very amused at the time.
01:17 Dave sucked on my hair.
01:23 9. Taylor Swift - The Ellen DeGeneres Show
01:27 During Ellen DeGeneres' reign as the Queen of Nice,
01:30 the harsher jokes on her talk show were generally taken in good spirits.
01:34 Taylor Swift seemed to be the only one who didn't take her 2012 interview in that way.
01:39 First, DeGeneres kept poking at disputed rumors that she dated Zac Efron.
01:43 Referencing the pop star's prolific love life,
01:49 DeGeneres eventually dragged Swift into a game where she would identify her exes in a photo slideshow.
01:55 The audience laughed hysterically as Swift became visibly upset.
01:59 Their tune finally changed in 2021 when allegations of workplace hostility
02:04 caused DeGeneres' fans to reappraise her public persona.
02:07 We have had a lot of conversations over the last few weeks about the show,
02:11 our workplace and what we want for the future.
02:13 We have made the necessary changes and today we are starting a new chapter.
02:18 Her grilling pop music's Queen of Nice for her personal life
02:21 stood out as a red flag that everyone just shook off.
02:24 8. Dolly Parton - The Tonight Show Starring Johnny Carson
02:47 Johnny Carson revolutionized banter for a late night audience.
02:51 His crude flirtations were considered fairly inoffensive for the time.
02:55 Now, audiences have particular trouble getting over a Dolly Parton appearance in 1977.
03:01 It's awkward enough that the conversation steered toward dismissing rumors
03:05 that she had work done on a certain area of her body.
03:08 Carson tried to be a quiet gentleman until he blurted out,
03:16 The audience burst out laughing, as did Parton herself.
03:20 With the racy chat's light tone, it's easy enough to accept the joke as a product of its time.
03:25 But wanting to inspect a popular rumor about country's biggest heartbreaker
03:30 still gets a more reluctant laugh nowadays.
03:33 7. Madonna - Late Show With David Letterman
03:44 Similarly, many David Letterman interviews with women haven't aged well.
03:48 Madonna's 1994 appearance on The Late Show was controversial at the time,
03:52 but maybe for the wrong reasons.
03:54 Most of her record 14 censored F-bombs were in response to Letterman
03:59 continuously joking about her sex life.
04:02 His suggestion that she go kiss a random man in the audience was particularly creepy.
04:11 The interview quickly became an iconic scandal for late night
04:14 because of the pop idol's salty language.
04:17 Modern audiences now find that easier to accept
04:24 than Letterman's sleazy spoofing of her unladylike candor.
04:28 The fun in Madonna's pushing edgy women forward is now spoiled a bit
04:32 by Letterman and his 90's audience's attitude about it.
04:36 6. Bill Cosby - Larry King Live
04:49 Bill Cosby's 2018 conviction for sexual assault permanently warped his legacy.
04:55 He actually may have never been that wholesome.
04:58 Do you have any sense why he might, if he did in fact, drug these women,
05:01 why he would have done so?
05:03 You know, I just have to assume that maybe he got excited over the idea of a woman being out.
05:09 I mean, I really don't know.
05:11 While multiple women were coming forward with accounts of being drugged and assaulted,
05:15 Cosby's 1991 interview on Larry King Live resurfaced.
05:19 Spanish fly was the thing that all boys from age 11 on up to death
05:27 We will still be searching for Spanish fly.
05:31 The comedian bantered about the disputed aphrodisiac Spanish fly
05:35 and described slipping it in women's drinks to lower their inhibitions.
05:39 It's hard to imagine anything humorous about these comments, even for the time.
05:44 They were bad enough for the prosecution in Cosby's trial to push to have them admitted as evidence.
05:49 This request was denied because Spanish fly is not a sedative.
05:53 Still, with the way Cosby talked about it, there's also more weight to his one-liner "Hello America".
05:59 And the girl would drink it and "Hello America".
06:03 Number 5. Anne Hathaway - Today
06:06 Matt Lauer's sketchy interactions with women were seriously reappraised
06:10 after allegations of sexual misconduct got him fired from Today in 2017.
06:16 His 2012 interview with Anne Hathaway especially stands out.
06:21 The future Oscar winner was promoting Les Misérables when Lauer immediately brought up her wardrobe malfunction at the movie's New York premiere.
06:28 Just get it out of the way, you had a little wardrobe malfunction the other night.
06:32 What's the lesson learned from something like that?
06:35 As she tried to tastefully move past this humiliating topic, Lauer kept it going.
06:40 He might have been noble in his criticism of the paparazzi profiting off of people's vulnerability,
06:45 but with her obvious discomfort, Hathaway seamlessly segued this discussion into her character of Fontyne.
06:52 Which brings us back to Les Mis, because that's what my character is.
06:54 She is someone who is forced to sell sex to benefit her child because she has nothing.
07:00 The irony in Lauer condemning sexualized exploitation would become clear not five years later.
07:06 His reputation now makes Hathaway's already awkward interrogation downright cruel.
07:11 I was very sad that we live in an age when someone takes a picture of another person in a vulnerable moment
07:17 and rather than delete it and do the decent thing, sells it.
07:20 Number 4. Ricky Martin, 2020
07:24 Latin pop sensation Ricky Martin endured years of gossip about his sexuality before he formally came out in 2010.
07:32 Where most interviewers respected his privacy, Barbara Walters saw it as another big scoop.
07:37 In an ABC interview in 2000, she accosted Martin about the rumors.
07:42 She eventually asked him point blank to declare whether he's gay.
07:45 Martin simply responded, "I just don't feel like it."
07:48 It would be another 10 years before he was ready to tell the world his truth.
07:52 Yeah, I felt like she was knocking like punch after punch after punch.
07:57 It was really uncomfortable to be honest.
07:59 But then again, I look at it and I'm like, "Why didn't I say yes back then?"
08:02 Just say yes, yes, I'm gay, who cares? You know what I'm saying?
08:05 Shortly afterward, Walters named trying to out him as the biggest regret of her career.
08:11 Martin himself remembers the incident as permanently traumatizing.
08:15 What once was an edgy or see tabloid standoff is now widely condemned as a violation by a respected journalist.
08:22 Number 3. Corey Feldman, The View
08:26 Clearly, Barbara Walters' confrontational interview style could dig a bit too deeply into personal lives.
08:32 When Corey Feldman appeared on The View in 2013, she tried to bury an important subject deeper.
08:38 I'm saying that there are people that were the people that did this to both me and Corey that are still working,
08:44 they're still out there, and they're some of the richest, most powerful people in this business.
08:48 The actor was promoting his memoir, Choreography, in which he alleges that many entertainment industry leaders sexually assaulted him when he was a minor.
08:56 Friend and fellow victim Corey Haim's own allegations had been met with skepticism for years before his death.
09:03 Even with Feldman's courageous confession, Walters responded with,
09:07 You're damaging an entire industry.
09:10 Her victim blaming was immediately controversial, but the fuss soon died down.
09:14 With the rise of the Me Too movement, Feldman's already uncomfortable scrutiny has resurfaced as a horrific stain on Walters' otherwise distinguished career.
09:24 I am using this to draw a line in the sand, to say to the Hollywood community, we are better than this.
09:31 #2 Danny Masterson - Late Night with Conan O'Brien
09:35 Danny Masterson's history of sexual assault resulted in his conviction in 2023.
09:41 This has permanently colored his legacy as well as his off-color sense of humor.
09:46 One joke during a 2004 appearance on Late Night is now particularly ominous.
09:51 The star of that 70's show mentioned an impression of him by Bodie Elfman, whose go-to line was,
09:57 Hi, my name is Danny Masterson, would you like to touch my balls?
10:00 Host Conan O'Brien appeared to be joking himself when he asked Masterson why he introduced himself that way.
10:05 He ended the conversation with, "I've heard about you, and you'll be caught soon."
10:09 Um, I've heard about you, uh, and you'll be caught soon, I know you will. I will.
10:14 With Masterson's crimes going back to 2001, O'Brien might not have been joking.
10:19 Either way, soon wound up being 19 years.
10:23 I got busted for possession.
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10:41 #1 Britney Spears - Primetime
10:45 Oh my goodness, hello. Ew, strong Britney.
10:51 Um, yeah, it was weird.
10:56 It took too long for the public to take pop legend Britney Spears' mental health seriously.
11:01 There's been a lot of speculation as to whether this is in Britney's best interest, and is this good for her, is this what she wants?
11:08 One notable reframed chapter in her downfall is a 2003 interview for ABC's Primetime.
11:14 Diane Sawyer dug into outrage at Spears over her breakup with Justin Timberlake, whose crude behavior has since come under scrutiny.
11:22 Timberlake has made a kind of sport out of public retaliation.
11:26 On a popular morning drive radio show in New York promoting his album, he has a kind of gleeful confession about their very private life.
11:34 The beauty icon was also scolded about her sexualization, shopping habits, and nervous tics.
11:40 Am I seeing what I think?
11:42 That's probably one of the moments that I remember I like the best.
11:45 You can pop your knuckles.
11:46 Britney Spears is popping her knuckles.
11:48 How do you do it?
11:49 After the interrogation brought Spears to tears, she became a laughingstock.
11:53 But the Me Too movement revealed the extent of the alleged exploitation from her representation and father.
11:59 She couldn't do much shopping when she was too depressed to leave her apartment.
12:03 Though the Primetime interview is now considered the tragedy it was, Sawyer has yet to apologize to Spears.
12:09 What classic celebrity interviews do you think have taken on a different meaning over the years?
12:14 Let's chat in the comments.
12:16 Everyone who was just behind you abandoned you.
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12:28 [music]