9 Most Memorable Celebrity Interviews

Published on August 28, 2014. Updated April 4, 2017

Interviews are part of the job for most celebrities. Celebrities need to promote their various movies, television programs and endorsements and what better way to do so than with a high profile interview. Many celebrity interviews are boring; however, there are a few out there that have gone down in pop culture history as being pretty interesting for a variety of reasons. Some of the celebrities who were interviewed just happen to give a really good interview while other times it is actually the interviewer who makes things interesting. Either way, we have collected 9 of the most memorable celebrity interviews – check them out and let us know which ones are your favorite!

9. Joaquin Phoenix

Back in 2010, Joaquin Phoenix made a rather bizarre appearance on the “Late Show with David Letterman.” Even though he was supposed to be promoting his film “Two Lovers,” the focus of the interview ended up centering on his strange behavior, disheveled appearance and his announcement that he was planning to retire from acting to focus on a career in hip hop. A year later, it finally came out that the whole thing was a hoax. Phoenix apologized to Letterman for his odd behavior and told him that the act was for Casey Affleck’s documentary “I’m Still Here.” You can see the interview below.

8. Paris Hilton

After she was released from jail back in 2007 for her DUI arrest, Paris Hilton gave her first interview to Larry King on CNN. During the interview, the former reality TV star took some responsibility for her actions, acknowledging that she has been immature and has made some questionable choices. She also tried, unconvincingly, to deny that she has ever tried drugs and claimed to have passed the time in jail reading the bible. Overall, it was a pretty funny interview, considering what we know about Hilton.

7. Stephen Colbert

In 2007, Stephen Colbert was a guest on the “Bill O’Reilly Show.” The interview was pretty funny because the comedian proceeded to impersonate the Fox News pundit on his right wing show all while pretending to admire him. O’Reilly did his best to crack his interviewee’s façade, but it was of no use. After the interview, Colbert stole a microwave from O’Reilly’s green room and then put it up for auction on eBay. Click below to see the hilarious interview for yourself.

6. Tom Cruise

Tom Cruise managed to totally humiliate himself when he went on Oprah’s show. He jumped up and down on her couch while declaring his love for the much younger Katie Holmes. His bizarre behavior had everyone scratching their heads. Oprah responded to the situation by laughing in disbelief and then telling him that he was “gone.” The Oscar-nominated actor was too drunk on his love for Holmes to notice how odd his behavior was. The whole thing still looks really awkward – even nine years after the fact!

5. Jennifer Aniston

Jennifer Aniston was interviewed for the “Scott Mills” show by Chris Stark and, while it wasn’t quite as amusing as the interview he had with Mila Kunis, it was still pretty good. The former television star was there to promote her film “We’re the Millers.” The interview ended up taking some pretty interesting turns. At one point, Stark asked her what she did to prepare for her role as a stripper in the film. Check out the video below to see her response!

4. Charlie Sheen

When Charlie Sheen was at his wackiest in 2011, he went on the “Today Show” and to no one’s surprise the interview was a total gong show. The controversial actor demanded a raise from $2 million to $3 million an episode to come back on the set of “Two and a Half Men;” he accused the show’s creator of trying to destroy his family; he claimed that he was able to overcome his drug and alcohol problems through sheer will power; and he asserted that he was a rock star from Mars. If you don’t believe us that all of this actually happened, watch the video below!

3. Drew Barrymore

When Drew Barrymore appeared on “Late Night with David Letterman” back in 1995, she put on quite the show. After talking about her striptease experience at a Manhattan nightclub, a young Drew asked Letterman if he would like her to dance for him. She then jumped on his desk, danced around a bit for him and the audience and then turned her back to the camera and flashed him. To this day, Letterman still remembers it, maybe because this all happened on his 48th birthday.

2. Mila Kunis

When she was promoting “Oz the Great and Powerful,” Mila Kunis proved just how congenial she can be in an interview with Chris Stark for the “Scott Mills” show. The British interviewer barely mentioned the film and proceeded to talk to the actress about his favorite local pub, a local football club and the drinking games he plays with his friends. Kunis was a great sport about the whole thing. She even considered going to his friend’s wedding with him before she realized she would be working that day. The interview went viral and you can watch below and see why!

1. Whitney Houston

During an interview with Diane Sawyer back in 2002, Whitney Houston appeared to still be using drugs, despite all of her denials. The Grammy-winning singer admitted to using alcohol, marijuana, cocaine and pills; however, when Sawyer asked if she used crack, Houston became indignant. “First of all, let’s get one thing straight,” she said. “Crack is cheap. I make too much money to ever smoke crack. Let’s get that straight. OK? We don’t do crack. We don’t do that. Crack is whack.” In spite of her protestations, no one believed Houston, not for a second!

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