The 15 Most Awkward Celebrity Interviews You Will Ever Watch

Celebrities are supposed to be best known for what they’re famous for, like acting or singing, but sometimes what gets everyone talking is their bizarre and awkward television interviews. Interviews are supposed to give the public insight into what celebrities are really like, but sometimes these interviews show us a strange side of these stars that we never thought we’d ever see. These interviews quickly become widespread across the internet, with people making memes out of them and generally laughing their heads off at these interviews gone wrong.

But they’re not always funny. Sometimes, these interviews are just plain weird. In some cases, celebrities do this on purpose as a publicity stunt, but sometimes they are so strange that they actually end up damaging their reputation. And there are those rare celebrities who couldn’t care less about their reputation, who seem to love going on television and being as strange as possible, just to mess with people’s minds and confuse them.

The actual goal of interviews is to make celebrities spill the beans on their deepest and darkest secrets, and most of the times these stars are tight lipped, knowing the tricks that interviewers will use to try to get them to open up. However, in extremely rare cases, celebrities make huge mistakes by saying things they totally regret, and those are the interviews that go down in history.


15 Eric Cantona 

Eric Cantona was undoubtedly one of the greatest footballers (soccer players) that ever lived. He was a genius on the soccer pitch, and Manchester United supporters used to sing his name loud and proud whenever he stepped onto the field. But he was just as famous for his antics off the pitch. He was known as a strange and eccentric fellow, and one with a hot temper. This all reached a boiling point when Manchester United played Crystal Palace, and Eric Cantona was sent off after a red card. As he was walking off the pitch, a Crystal Palace supporter shouted at him, “F**k off back to France, you French motherf**ker!” That’s when all hell broke loose. Eric Cantona launched himself into the stands with a vicious kung-fu kick, smashing the supporter squarely in the chest. He was subsequently banned from football for life. He later gave this interview to the press. This is all he ever said to the press, and people are still trying to figure out what it meant.

14 Shia LaBoeuf


When Shia LaBoeuf gave this press conference, he was already shrouded in controversy. He had just finished wearing a brown bag on his face for days. He had finished his newest Transformers movie, which proved to be a complete disaster, and he was gaining a reputation as a wild child with several incidents involving him getting into fights with random people. The reporters present desperately wanted him to say something so they could put it on the headlines. And he gave them something alright. He completely copied Eric Cantona’s famous speech. Not many people knew who he was referencing at that moment, and that just made it all the more weird.

13 Kanye West, Part One

Now many people would agree with what Kanye said in this television appearance. It’s true, what happened in Katrina was a real tragedy, and perhaps the government could have reacted faster in getting those affected to safety. That’s not for us to say. But the manner in which Kanye delivers his speech is just plain awkward. On his left you have Mike Myers, who delivered his message to the people in a calm, yet concerned manner. Then, when Kanye speaks you can see Mike Myers immediately start to cringe, and he looks like he wants to distant himself from what the guy on his right is saying. I get that Kanye might have been emotional after what had happened during Katrina, but this speech really just came off as strange...

12 Kanye West, Part Two


This is probably one of the strangest interviews you will ever see. The funniest part of this is the look on Ellen’s face the whole way through. Why the hell did she even decide to have Kanye West on her show? She’s probably regretting that decision right through this video. Where do I begin? There’s the huge awkward silences with Kanye staring into the audience. His tendency to break into rap mid-conversation. And the way he raises race issues and seems to get increasingly angry. Then he begins to swear constantly on what is supposed to be a family, “feel-good” talk show. He just seems so out of place on a show like Ellen. And probably the most bizarre thing about this interview is that it’s basically just Kanye speaking, Ellen is just allowing him to rant on and on, and nothing (and I do mean nothing) he says makes any sense whatsoever.

11 James Brown

Some of the funniest interviews happen when the person being interviewed is clearly on drugs. That’s what happened when James Brown was interviewed immediately following his divorce after he allegedly beat his wife. James Brown doesn’t really seem too interested in actually communicating in this interview. He answers all of the questions with lyrics from his songs, like “Livin’ in America!” Or “It’s a man’s world!” He even wipes his nose right before the interview begins, and can’t seem to stay in his seat for its duration. Who knows whether he was actually on drugs or not, but I think it’s safe to say that his behaviour was strange, questionable, and yes, undoubtedly hilarious. He can’t seem to stop reminding American viewers that “He feels good!” Yes, James Brown, that is pretty easy to see.

10 Joaquin Phoenix


As soon as Joaquin Phoenix walked onto the stage of The Letterman Show, it was clear that something was up. Joaquin looked insane. He had a huge shaggy beard, long hair, and strange sunglasses that he refused to take off. For most of the interview, he sat in silence, looked uncomfortable, and seemed offended when the audience laughed at him. The awkwardness reached a climax when Joaquin revealed to Letterman that he was ending his acting career - in order to become a rapper. The audience laughed once again, but Joaquin was not joking. Letterman himself seemed to take offense on account of Joaquin’s antisocial behavior, and he was just as perplexed as the audience. Clearly, this was not scripted. Years later, Joaquin apologized and confessed that at the time of the interview, he was in character, as he was filming a mockumentary at that time.

9 Charlie Sheen

We all remember the intensity of Charlie Sheen’s downward spiral, and this interview was probably one of the most memorable moments of that whole debacle. “Bi-winning” even became a catchphrase that spread across the internet, and it was turned into a meme and repeated across the world. Charlie Sheen is so fascinating to watch in this interview. He claimed that he was off drugs at the time of the interview, but judging by his behaviour, the truth of that statement is thrown into question. He is even asked at one point, “When was the last time you took drugs?” To which he replied, “I can’t remember.” He even brags about his partying, saying it would put Mick Jagger and Sinatra to shame. This is probably one of the funniest, most awesome, and craziest interviews of all time.


8 Micheal Jackson


This is the interview that ruined Michael Jackson. A hard-hitting BBC interviewer pummelled Michael with questions until the pop star cracked. Then, everything came out. This was the first time he admitted to sleeping with children in the same bed. There is something extremely weird about the way Jackson tries to play it off. He says, “It’s love, it’s loving.” Just the way he speaks is extremely creepy. Whether he did it or not, who knows. But you can see how this interview went down in history as one of the strangest moments ever caught on tape. In the end, he admits that he paid the families of these kids to stay quiet. Is that weird? You be the judge...

7 Madonna And Courtney Love

It’s not every day you see a celebrity’s interview get crashed by another celebrity. But that’s precisely what happened to Madonna after MTV’s VMA awards. Everything was going fine, when suddenly shouting is heard from down below. Madonna’s interviewers says, “Is that Courtney Love?” And then something is thrown at Madonna. Soon after, Courtney Love appears, and sure enough she is completely drunk. The interviewer seems thrilled at first, because after all, now he can interview two stars at the same time! But his excitement soon turns to uncomfortable regret as Courtney Love’s behaviour gets more and more insane. She even ends up on the floor at one point.

6 Miley Cyrus


In an interview the world will never forget, Miley Cyrus strutted onto the stage of a talk show wearing something completely scandalous, even for Miley. Instead of wearing a shirt, like a normal girl, she wore something very… adventurous. She didn’t even wear a bra. What Miley Cyrus decided to wear that day was two “pasties,” small stickers that are meant to cover the nipples, and not much else. Jimmy Kimmel was so distracted he could hardly stammer out sentences, let alone questions. This was a clear publicity stunt, and it definitely served its purpose. Miley Cyrus got the attention of the whole world that night.

5 Cristiano Ronaldo

In this interview, Cristiano Ronaldo revealed to the internet that he really doesn’t care what anyone thinks. An athlete that has had as much success as him is bound to be confident, but this gives the word “cocky” a whole new meaning. He doesn’t want to answer the interviewer's questions about the FIFA corruption scandal, because according to him, it doesn’t concern him. In his own words, all he thinks about is shoes, haircuts, and women. When the interviewer continues to try to ask about FIFA, this high-paid athlete gets angry and storms out. Maybe it’s because he wanted to talk about his new gold headphones instead.

4 Ben Affleck


This interview went down in history as one of the funniest ever. The interview by itself was undeniably hilarious, but when the internet went to town and mixed it with “Sounds Of Silence,” it reached a new peak of hilarity. I don’t know what’s funnier, the fact that Batman Vs Superman was a box office flop, or the fact that Ben Affleck seems so sad about it. This video has been seen by pretty much everyone, and you can see why. Ben totally zones out, and when the interviewer asks him for his opinion, he simply says, “I agree.” Classic.

3 Alex Jones

For those of you who don’t know, Alex Jones is basically the granddaddy of all conspiracy theorists. No theory is too crazy for Alex Jones. The internet loves him, as he is constant source of hilarious rants about chemicals in the water that are making frogs gay, or reptilian shapeshifting aliens disguised as politicians. In this rare interview, Alex Jones goes up against Piers Morgan, a conservative guy with very mainstream views. This interview proved to be one of the funniest, most awkward meetings between two guys who are basically polar opposites. Alex Jones starts to power up into full tinfoil hat mode, and Piers Morgan gets more and more pessimistic and dismissive of Alex’s theories. It’s a truly golden comedy moment.

2 Tom Cruise


Never ask Tom Cruise about Scientology. That’s what this interviewer learned - the hard way. As soon as Scientology is mentioned, Tom Cruise seems to become a completely different person. Things start to get awkward, and it only get worse as the interview goes on. Now, Tom Cruise may actually be right about drugs like Ridalin, and maybe we shouldn’t be giving our kids that. But it’s the manner in which Cruise speaks that makes this whole interview extremely strange. The interviewer has clearly struck a nerve, and Tom seems angry and dangerous. In the end, he states that he wants more people to join the religion of Scientology.

1 Crispin Glover

Best. Interview. Ever. That's all I can say about Crispin Glover's appearance on The Letterman Show. Glover is so inescapably weird, so unique and so unpredictable that it makes David Letterman noticeably alarmed and nervous, and that's just awesome. Glover comes into this interview as some kind of strange character, wearing high heeled boots and some insane looking pants. Then he gets more and more insane and crazy as the interview goes on. He even looks offended when the audience when they laugh at his weirdness. It all ends with Crispin Glover kicking the air in front of Letterman, and that causes the host to cut the show off the air and go to a commercial break. That was the end of Crispin Glover's interview.

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