Top 10 Brutally Honest Celebrity Interviews

When Michael Jackson and Lisa Marie Presley got married in 1994, people were skeptical of the relationship. Presley had divorced Danny Keough 20 days before, and the public accusations of child molestation against Jackson had already been surfacing for a few months. Diane Sawyer began by asking typical relationship questions on ABCNews’ “PrimeTime Live” in 1995. But she quickly put the couple on the defensive, asking about their decision to marry and the allegations. It’s hard for an interview not to get awkward with these subjects, but Michael maintained his innocence and Lisa Marie stood by her man. Diane has been criticised for trying too hard to get a scoop, much like Martin Bashir later was for his 2003 TV documentary with Michael.

It’s no secret that Tom Cruise is a devout Scientologist, and he’s not afraid to defend his beliefs. During this 2005 “Today” interview with Matt Lauer, the topic of antidepressants comes up and things get… heated. Tom isn’t shy about criticizing prescription medication or modern psychiatry, and Lauer took the star to task for his judgment of Brooke Shields for using medication to deal with Postpartum Depression. Lauer tries to defend the other side of the argument, but Tom refuses to concede, boasting about his superior knowledge of the subject. It’s pretty awkward to watch, but there’s always something to be learned from “bad interviews,” and in this case, the world definitely learned more about Tom Cruise.

Where to even start with this infamous 2011 interview? It has been quoted in every medium imaginable, from internet memes to psychology magazines. After Sheen’s contract for “Two and a Half Men” was terminated, Sheen’s career took a nosedive, as documented by the series of bizarre interviews he gave around that time. But this was the one to beat. Speaking with ABC’s Canning, he speaks frankly about serious issues, like drugs and the show, but also injects them with memorable outbursts, like his comment about having ‘tiger blood’. Sheen has since attributed these outburst to ‘roid rage’ and he refers to his interviews as ‘cringeable.’ Cringe-inducing or not, they were definitely eye-opening.

This 2003 interview happened at a very vulnerable time in Britney’s personal life; she was only in her early 20s and her breakup with Justin Timberlake was still very raw. Despite all this, she doesn’t back down from any questions asked, she defends her choice to show skin in magazines, she denies any drug use and she openly breaks down when talking about Timberlake. Sawyer even inquired about Britney’s sex life, asking if she still believed in staying a virgin until marriage. Britney was no stranger to interviews or public scrutiny by this point, but for better or worse, she answered even the toughest and most personal questions with apparent honesty.

It can’t be stressed enough that the public loved Diana; she was truly the people’s princess. Everyone wanted to know more about her life, especially about her divorce from Charles, and in that regard, this 1995 BBC Panorama interview definitely delivered. Diana was extremely candid and opened up about her bulimia, depression, infidelity in her marriage, and what it was like living as a royal. Diana also seems very vulnerable, her voice full of sadness as she says to Martin Bashir, “there were three of us in this marriage...” 22.8 million people tuned in to watch; she spoke her truth and the world listened.

Oprah doesn’t like to be deceived; in fact she downright hates it. She was swept up in Lance Armstrong’s story just like everyone else and when it was revealed in the eary 2010s that he was using performance-enhancing drugs, she too felt duped and cheated. The iconic television personality made it a point to confront him personally and she doesn’t try to hide her disappointment in this interview that aired in 2013. Oprah didn’t accept lies or excuses - she wanted the truth and that’s what she got. In it, Lance admits that he lived a lie, and he finally confesses to doping. It’s really hard to lie to Oprah, which is why she’s mastered the art of the confessional interview.

What started out as an interview with a husband and wife ended in shocking revelations and ultimately divorce. Originally the 1988 interview was about Tyson but Givens joined, and she had a lot to say. Instead of talking about marital bliss, Givens gives a bleak account to Babara Walters of their 8-month marriage, accusing Tyson of being abusive. Givens doesn’t hide the fact that she’s unhappy and even scared of her husband. Tyson is clearly shocked, and sits in silence for most of the talk. Though Givens said they were working on his issues, she filed for divorce just one week after the interview and cited irreconcilable differences.

This was the moment Caitlyn Jenner finally decided to announce to the world that she was transgender. In this emotional and groundbreaking 2015 interview, Jenner talks about what it was like being perceived as a macho-male Olympian while a feminine voice inside screamed to be heard - how isolating it was to be a celebrity and not wanting to disappoint her fans. In a lot of ways, this is the moment she said goodbye to who she had been, and took ‘the damn ponytail out’. Jenner and Sawyer would have yet another eye-opening interview together 2 years later.

She’s the intern that almost brought down a presidency. A month after Bill Clinton was acquitted for lying about his affair with Monica Lewinsky, Lewinsky decided to tell her side of the story. 70 million people ate up the Barbara Walters interview and Lewinsky didn't disappoint, speaking out about her relationship with Clinton, how she felt about him and everything in between. It turns out that she didn’t just have sexual relations with that man, she was also in love with him. The 1999 interview was also a launching point for Lewinsky’s pop culture stardom and various endeavors in fashion and television, among other ventures.

Before we reveal our top pick here are a few honorable mentions.

Quincy Jones with Vulture
2018

Fidel Castro with Barbara Walters
1977

Robert Blake with Piers Morgan
2016

Whitney Houston with Diane Sawyer
2002

R. Kelly with Gayle King
2019

The Watergate scandal shook the very foundations of America, and the man at the heart of it wasn’t saying too much. It wasn’t until 1977, three years after he retired as president, that Richard Nixon finally opened up in a series of interviews with David Frost. Here, he admitted more than he ever had before, with 45 million people watching. Frost was specifically chosen because Nixon’s team thought he was a pushover, but they were sorely mistaken. Frost asked what the American people wanted to know, and by the end he had Nixon apologizing and admitting to failing the country.