Old Celeb Interviews That Are Super Awkward Now
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Old Celeb Interviews That Are Super Awkward Now

October 16, 2019


It’s always best to hold your tongue in Hollywood. After all, a single slip-up can forever tarnish
a celebrity’s reputation. Don’t believe us? Take a look at these vintage celebrity interviews. They’re unbelievably awkward in every way,
so prepare to cringe! Charlie Sheen had a rough 2011. That year, he was fired from the CBS sitcom
Two and a Half Men, and there’s nothing funny about suddenly finding yourself unemployed. There’s also nothing funny about Two and a
Half Men. “I said I’m sorry. I am sorry. I am! I am! All right, I’m not.” According to The Telegraph, Sheen was fired
from the show because of an out-of-control drug habit. An awkward 2011 interview sheds light on his
frayed mental state at the time. After months of erratic behavior, an interviewer
told Sheen that a lot of fans suspected he was bipolar. Sheen’s response? “I’m bi-winning. I win here, and I win there. Now what?” After a discussion about drug use, Sheen claimed
he was clean: “I’ve just answered to a higher calling, and
it happened in a blink of an eye.” But the most notorious soundbite from the
interview has to be this: “I’m me, I’m different. I’ve got a different constitution. Different brain, a different heart. I got tiger blood, man.” No matter how many years go by, this interview
between actor Jesse Eisenberg and blogger Romina Puga will never not be awkward. “Yeah… That one… I think what you’re doing is you’re putting
your thumb under your pointer finger.” Eisenberg was promoting his 2013 film Now
You See Me… but the interview went south before Puga finished asking her first question. Eisenberg gets conspicuously prickly after
she refers to his costar Morgan Freeman by only his last name: “So Freeman plays, uh… a magic debunker.” “Freeman? Who are you? Freeman? What, are you on a baseball team with him?” “Yeah he’s a buddy of mine.” “Okay.” And that’s just the tip of this particularly
chilly iceberg. Seemingly feeding off Puga’s nervousness,
Eisenberg says to her: “Um, do you know the, um, comedian Carrot
Top?” “Yes. Horrible.” “Well. You are like the Carrot Top of interviewers.” “Ooh.” Following the interview, Puga wrote: “So, I was just humiliated by Jesse Eisenberg. […] The five minute ‘interview’ [was] more
like self-esteem butchering.” Years later, Eisenberg told Business Insider
he doesn’t enjoy doing press — as though that wasn’t already abundantly clear. He explained: “Ninety percent of it is concern that I’m
going to misspeak, because I have in the past, and that seems to be the overriding narrative
regardless of the intention or relevance. So that’s a lot of what this is.” Way to let yourself off the hook, Eisenberg. Back in 2005, an alarmingly giddy Tom Cruise
appeared on The Oprah Winfrey Show, quite literally jumping for joy at the mere mention
of his then-girlfriend, actress Katie Holmes. “That’s how I feel about it!” And who can forget when Cruise expressed his
love for Holmes by jumping up and down on Oprah’s couch? We can’t. “So this is interesting, Tom. We’ve never seen you behave this way before.” “I knooooow.” The epic talk show appearance has spawned
countless memes — and was notably satirized in the otherwise unmemorable Scary Movie 4. “Wow.” Throughout the very out-there appearance,
Winfrey keeps declaring: “He’s gone. I’ve never seen him this way.”] “He’s gone, Katie! He’s gone!” “So this is beyond smitten. This is gone.” “I’m standing on your couch! Ha ha ha!” Cruise and Holmes got hitched in 2006, but
the marriage didn’t last. Holmes filed for divorce in 2012, asking for
“primary residential custody” of their daughter, Suri. In a showbiz career spanning multiple decades,
Madonna has perfected the fine art of dissing her fellow pop stars. In 2012, she said of Lady Gaga’s music: “It feels… uh… reductive.” “Is that good?” “Look it up.” Madonna’s shade was just a touch more subtle
during a now-legendary interview at the 1995 MTV Video Music Awards. As Madge dutifully answers Kurt Loder’s questions,
a makeup compact suddenly whizzes past her: “You may say it’s a reflection of that…
but it’s also—” Loder and Madonna look down below, and guess
who they see? Hole frontwoman Courtney Love! Loder is rather keen to have Love join in
on all the fun. Madonna, quite clearly, is not. “Come on up!” “Should we let her come up?” “Yeah.” “No, don’t, please.” “Come on, Courtney!” As Love acts out, a helpless Madge mumbles: “Courtney Love is in deep, dire need of attention
right now.” Later on, awkwardness reigns supreme as Love
sits with Madonna and Loder. “Sorry I insulted you. I was in a bad mood. But you said something mean about me that
day.” Then there’s a lot of this kind of thing: “No, I interrupted you… “No, no, no… I’m gonna leave you two.” “I ruined my Mac compact!” It’s an absolutely iconic segment that never
fails to Make. Us. Cringe. “You sit in the chair.” “No I don’t want to sit in your chair.” “No stay there.” “…it’s like a throne.” Plenty of folks are familiar with Jerry Seinfeld’s
exceptionally uncomfortable run-in with Kesha in 2017. He denies her a hug not once, not twice, but
three times! “… ‘cuz people are tired most of the time.” “… I love you so much!” “Oh thanks.” “Can I give you a hug?” “No thanks!” “Please?” “No thanks!” “A little one?” “Yeah — no thanks!” “Ohhh.” Fans were horrified — and so was Kesha. She later told radio station Hits1: “I had a moment where I was thinking to myself,
‘Wow, maybe I should stop trying to hug everyone and, like, attack them.'” “He’s not a huggy guy, that’s fine.” Meanwhile, Larry King had his own painfully
awkward encounter with Seinfeld in 2007. While interviewing the comedian on CNN’s Larry
King Live, the talk-show host unwisely asked about the end of Seinfeld’s hit sitcom on
NBC: “They didn’t cancel you… you canceled them?” “You’re not aware of this?” “No, I’m asking you.” “You think I got canceled?” Granted, King probably should’ve known that
Seinfeld chose to end the series. In fact, he reportedly turned down a lucrative
offer from NBC to the tune of $5 million per episode. Seinfield’s withering sarcasm is on full display
during the clip: “is this still CNN?” “Don’t most shows go down a little?” “Most people do, also.” That is some high-octane awkwardness right
here. When Keeping up with the Kardashians launched
in 2007 on the E! Network, many viewers became obsessed with the family. Around Season 4, famed journalist Barbara
Walters put the entire clan on ABC’s 18th annual “10 Most Fascinating People” special. Clearly, the KarJenners had already earned
some haters at this point, because Walters opened her segment with: “I have never heard more anger or dismay then
when we announced that the people you’re about to see were on our list.” Oh dear. Sitting down with Kim, Kourtney, and Khloe
Kardashian and momager Kris Jenner, Walters starts her interview with the following blunt
statement: “You don’t really act. You don’t sing, you don’t dance. You don’t have any — forgive me — any
talent.” “But we’re still entertaining people.” After some back and forth, Khloe actually
ends up agreeing with the host! “Like, none of us think we have talents. Like, none of us think we could sing or act
or dance.” Hey, fair enough. But fast forward a few years and the KarJenners
are more famous than ever. Kylie Jenner and Kim K have their own makeup
empires; Kendall was the highest-paid model in 2018; and Khloe launched Revenge Body,
her own fitness reality TV show. As for Kourtney? In 2019, she debuted Poosh, a Gwyneth Paltrow-style
lifestyle blog. So they aren’t singing and dancing… but
whatever they are doing seems to be working. Ben Affleck is a bonafide Hollywood fixture. The actor-turned-director has been attached
to countless high-profile films over the years… but in 2017, fans were intently focused on
a pair of old interviews that suddenly resurfaced. At the height of the Harvey Weinstein scandal,
Affleck spoke out against the disgraced movie mogul on his Facebook page, writing: “I am saddened and angry that a man who I
worked with used his position of power to intimidate, sexually harass and manipulate
many women over decades. The additional allegations of assault that
I read this morning made me sick.” Shortly after he posted the message, fellow
A-lister Rose McGowan called out Affleck on Twitter. She claimed he knew all about the allegations
made against Weinstein. “‘I TOLD HIM TO STOP DOING THAT’ you said
that to my face.[…] You lie.” Around the same time, One Tree Hill alum Hilarie
Burton shared her own Affleck horror story from 2003, explaining that the actor acted
inappropriately during a TRL interview. “You’re always like, ‘I’m just free-spirited. It’s so nice to see you.'” “And he wraps his arm around me and comes
over and tweaks my left boob.” In an October 2017 tweet, Burton opened up
about the incident: “Girls. I’m so impressed with you brave ones. I had to laugh back then so I wouldn’t cry.” The next day, Affleck apologized for his behavior
in a tweet: “I acted inappropriately toward Ms. Burton
and I sincerely apologize” Things went from bad to worse for Affleck
when another old interview started making the rounds. In that one, Affleck is canoodling with Canadian
interviewer Anne-Marie Losique of Box Office. During a 2004 press tour for Jersey Girl,
Affleck asks Losique: “Well you used to show a lot more cleavage
than this. What’s the story? Why are you covering it up today?” “Well it’s Sunday morning.” “Sunday morning?” At another point in the interview, this happens: “I like this perfume. They would like it better if you do the show
topless, the station would.” After the video resurfaced, Losique told Entertainment
Weekly: “I want to make it very clear. It was strictly for the cameras, while the
cameras were on. While they were off, he was actually very
proper and we talked about many things.” Regardless of what went on behind the scenes,
what happened while the cameras were on is certifiably squirm-inducing. Agreed? “Oooouunghh… you think we can do the interview
like this.” Gene Simmons Being in a committed relationship with KISS
bassist Gene Simmons must be hard. After all, he claims he’s bedded down around
5,000 women in his lifetime. So we have to give it to Simmons’ wife Shannon
Tweed, the mother of their two children. In 2011, she held her own during an exceedingly
awkward interview on The Joy Behar Show. In the wake of cheating allegations against
Simmons, Tweed remarks: “He’s a pig and I don’t like it.” “He’s a pig?” “And I’m… I’m done.” “You’re finished with him.” At one point, Simmons seemingly tries to let
himself off the hook: “Men are basically 12-year-old boys.” “There you go, giving yourself company.” Later on, Behar tries getting to the root
of the matter: “You have been together a long time, you have
your… philandering ways. Is that…?” “There you go. I like that word.” Then Behar alludes to Simmons’ various sexual
trysts: “How’s your back, Gene?” “My back is good, my schmeckle not so much.” “That’s very nice for you to joke about.” “It’s a joke!” And with that, Tweed gets up and leaves the
interview. “Please come back.” “I don’t want to, you joked about it and it
isn’t funny.” “Well I’m trying to make you feel a little
more comfortable.” So that happened. But because love is a wild and crazily unpredictable
beast, Simmons and Tweed wound up getting married a few months after the interview. In May 2018, Simmons seemed to admit to his
wrongdoing, telling Us Weekly: “The astonishing thing about women is … I
don’t know why, but you forgive our trespasses over and over, every single day. Guys wouldn’t do that.” Jonah Hill seems quite pleased with how his
acting career is going. In a 2013 interview with Rolling Stone, he
mused: “I’ve done one of the biggest challenges you
can do in Hollywood, which is transition from being a comedic actor to being a serious actor,
and I’m really prideful of that.” Perhaps that statement has something to do
with an interview he conducted with his Moneyball co-star, Brad Pitt. Posing a fan question, Hill asks: “If you could adopt a personality trait or
mannerism from one of your Moneyball costars, who would it be?” Hill points out that Pitt can pick literally
any co-star — including a certain special someone: “Anyone sitting right here… That could be one of them.” Pitt’s response? “Yeah, no. Yeah, no. I gotta go with a serious actor.” Ouch! Hill seems understandably uncomfortable following
the exchange, rendering the rest of the interview rather difficult to watch. These days, Hill can probably laugh about
it. After all, his Moneyball performance earned
him an Oscar nomination for Best Supporting Actor. Plus, in 2018 he starred in the Netflix drama
Maniac, and made his directorial debut with the 2018 coming-of-age film Mid90s. As Hill would tell The Guardian in 2019: “All actors are typecast, but I tried to change
whatever pigeonhole I was in because I didn’t want to get stuck there.” The ’60s were an altogether different time,
with the concept of modern feminism only slowly creeping into the mainstream. Meanwhile, James Bond — portrayed by actor
Sean Connery — was the epitome of masculinity on the silver screen. “I admire your luck, Mister …?” “Bond. James Bond.” In a 1965 interview with Playboy, the Scottish
actor was asked: “How do you feel about roughing up a woman,
as Bond sometimes has to do?” Connery’s response is a jaw-dropper: “I don’t think there’s anything particularly
wrong about hitting a woman. […] If a woman is a b—-h, or hysterical,
or bloody-minded continually, then I’d do it.” What’s worse, Connery didn’t back down from
that statement during a 1987 interview with Barbara Walters. The famed journalist made sure to bring up
the old quote, asking Connery: “Remember that?” “Yeah.” “I didn’t love that.” “I haven’t changed my opinion.” In fact, Connery even says: “I don’t think it’s that bad. I think that it depends entirely on the circumstances.” Asked what situation would “merit” slapping
a woman, Connery offers this response: “They want to have the last word and you give
them the last word, but they’re not happy with the last word. They want to say it again.” A clearly gobsmacked Walters asks: “What if she gives you a good slap back?” “Well… then you get into another area. Then maybe she’s getting to like it, and it
becomes something else, I don’t know.” That interview was awkward when it first aired
in 1987, and it’s beyond awkward now. Check out one of our newest videos right here! Plus, even more Nicki Swift videos about your
favorite stars are coming soon. Subscribe to our YouTube channel and hit the
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  1. I'm on Jessie Eisenberg's side. Too bad she couldn't handle his wit and sarcasm. BTW nobody in the world has referenced Morgan Freeman as …"ehh..this guy ..Freeman".

  2. Sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy sexy

  3. It's not an excuse, but Jesse Eisenberg is neurodivergent, and that can manifest in awkward conversation, saying things you don't really mean, unnecessarily raised tempers… However, as a neurodivergent person myself, I'm not going to insult a stranger, no matter how playful I think I'm being! Comparing her to Carrot Top is a low blow.

  4. They try to defend all Kardashians in the end with makeup empire blablabla. But in the end all the skill from the Kardashians is only really coming from Kourtney. Because of that I am at least neutral on my opinion of her, but I dislike the rest of them even if Kim has married Kanye West, a great artist who is an SUPER-EXCENTRIC musician. 😉

  5. I was 13-25 years old when 2 and a half men aired n never liked it, yet my dad n all my friends dads who were late 40s early 50s all loved it

  6. Ben Affleck is just vile. It wasn't shown here but he also insulted disabled people during the interview with the French woman. Disgusting and shameful

  7. And that's why i get so irked when people say he's the best bond….he's such a joke of a man, glad connery will be remembered as so

  8. Far from being simply awkward, Charlie Sheen’s 2011 interview is legendary and iconic! He changed the English language forever, introducing the idioms, “Come on bro, I’ve got tiger blood,” “winning,” “winning against the trolls,” and “I was banging 7 gram rocks, that’s how I roll.” Trolls: 0 Sheen: 1,000.

  9. So glad Jesse eisenberg mediocre acting ass is not around from what I can see.Brad Pitt to me is just blah….Ben Affleck is so damn forgettable.Tom Cruise seems like if he would just get away from scientology he'd be cool. Seinfeld was and has always been corny to me. Everyone on that show was funny except him.

  10. Referring to Morgan Freeman as "Freeman" is plain disrespectful.
    Jesse Eisenberg was correct to set the interviewer straight.

  11. they are times where its okay to hit a woman, have you ever been stabbed by a crackwhore? now with your missus thats a different story, well unless she herself is also a crackbaby.
    The only time It is okay to slap a woman is in an arguement when she starts to get violent and pushing and shaking her whilst trna calm her down when talking to her just isnt getting her emotions back in control, thats when its okay to slap your missoes… apart from that its only ever okay if shes got a gun aimed at you or she has attepted to stab/cut you. those sitsuations to arise, everyone is capable its just up to them if they want to try and handle that path.

    No I have never hit a woman in my life outside of a gym.

  12. Charlie sheen is the most sad man 2 me. He literally spoke like he was proud of how many women he slept with, how much booze he drank and how much dope he did. All in the same time getting arrested 4 DUI's, drugs, abusing women, assault and who else knos what. He was getting fired and not getting along with costars. 2 top it off the POS now has HIV, that's terrible 4 all those poor women he slept with, who knos how many people he has infected over the years. U can c his decline in his health over the years on tv, the fact of the matter is u can have the fuken disease 4 ever without showing symptoms. HOW MANY HOLLYWOOD STARS HAVE HIV/AIDS AND R KEEPING IT HUSH HUSH. CHARLIE SHEEN HAS LITERALLY SLEPT WITH MINIMUM 50 WOMEN, HOW MANY OF THEM R FAMOUS. THEN HOW MANY WOMEN PERIOD, PERIOD, PERIOD, LIVES HAS HE WRECKED. With those women, they then sleep with other partners, then so on and so on. My God, the power this man had in Hollywood and beyond. Really shitty.

  13. Alcohol is not Ben Aflecks friend. It was not just a regular TRL episode. It was a house boat party spring break segment. Producers encouraged Ben to drink for audience amusement. It is good he apologizied. But MTV producers need to share the blame for getting Ben liquored up.

  14. “Affleck reached around and touched my left boob. (On spring break)”. Whip de doo. You’re an adult. If a woman touched Affleck’s boob, would he cry about it like that? Geez. Coocoo lady.

  15. “Fellow A-Lister Rose McGowan.”

    I mean, I love Rose but she’s hardly an A-lister. Also, the clips used when talking about Hilarie Burton are mainly of Bethany Joy Lenz in OTH.

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