Top 20 Most Brutally Honest Celebrity Interviews

2024
Grande is one of countless celebrities who can barely take a breath without someone commenting on her body. Imagine how exhausting it must be to hear the same tired narrative, especially when all you want to discuss are your proudest achievements. During the “Wicked” press circuit, Grande got emotional when asked how she handles such relentless scrutiny. While it’s not the first time she’s addressed the topic, it’s clear this issue has weighed heavily on her, and she uses the opportunity to express her feelings. You can see how deeply she feels about it. Grande seems hopeful this might mark the end of that wider conversation. One can only hope!

2016
Bennifer had been married for ten years, and one day, when they announced to the world that it was over. Naturally, the rumor mill quickly churned out whispers of infidelity, particularly involving Affleck and the family’s nanny. In an interview with Vanity Fair, the actress addressed her divorce, clearing up rumors and reflecting on the toll it took on her young family. She shares how the media’s obsession with her personal life forced her to step back and block out the noise. She still had plenty of praise for Affleck, though her pain is very clear. She also seems to borrow from “The Talented Mr. Ripley” to describe her relationship with her ex.

2018
It’s no surprise that being a woman in the workforce—especially in Hollywood—comes with plenty of challenges. In an interview with Hollywood Reporter, the “Grey’s Anatomy” star shared how she learned to recognize her worth and fight for it. She opens up about the double standards in the industry and how having a major Hollywood actor as a co-star often made her feel boxed in. When Patrick Dempsey left the show, she decided it was time to remind everyone whose name is in the title. As Pompeo notes, women in Hollywood are often treated like they have a sell-by date, so why not demand your worth? That’s how you become one of TV’s highest-paid actresses!

2018
Dunham has never shied away from being transparent about her personal life. Before her interview with The Cut, Dunham had undergone surgery on her ovary. From the way things are described, she gave her interviewer such a vivid account that it was almost like they’d had a front-row seat to the procedure. By the time they met, they were already well-acquainted with Dunham’s organs. She speaks candidly about her battle with endometriosis, the drastic steps she took to manage the pain, and how she felt validated by her doctor after the surgery. Dunham also addresses the gossip about her misfortune with pets and reflects on the past statements for which she’s had to apologize.

2018
“I know too much, man,” Quincy Jones told his interviewer, and after decades in the business, he’s certainly likely to have seen and heard it all. In this candid interview, Jones spills on Michael Jackson’s alleged plagiarism, his unfiltered thoughts on the Beatles, his ties to former presidents, and even his take on who shot Kennedy. He also claims to have dated Ivanka Trump—and he doesn’t hold back when it comes to her father! Jones even brings up Marlon Brando’s rumored romantic history and sexuality, though Brando’s son has since denied at least part of those claims. Ironically, the person we seem to learn the least about in this whirlwind of revelations is Jones himself.

2022
While promoting his memoir, Matthew Perry gave this deeply honest interview about substance use disorder and how it consumed his life. Diane Sawyer picked out some of the book’s most painful moments, and Perry addresses each one with remarkable candor. He opens up about the cost of fame, the grip of addiction, and how it nearly ended his life. It’s clear how important it is for him to share his story, hoping to inspire others facing similar struggles to find hope. Listening to him speak so openly, willingly revisiting his pain to help others, is both moving and admirable. This interview feels even more devastating now, knowing the challenges he faced and how his story ends.

2002
After endless speculation about her health and relationships, Whitney Houston sat down with Diane Sawyer to set the record straight. She speaks openly about her struggles with substance use disorder, though she frames it as a “bad habit.” She also reflects on how it impacted her life and credits her faith for giving her the strength to persevere. Sawyer’s questions are relentless, leaving little room for Houston to deflect, yet she tackles them head-on. Houston addresses everything: her addiction, body image, legal disputes with her father, and even her relationship with then-husband Bobby Brown. She also touches on behaviors the public had labeled “erratic.” She makes it very clear that she won’t let tough questions diminish her resilience.

2016
Piers Morgan has a habit of provoking strong reactions, and actor Robert Blake is no exception. While discussing his memoir, Morgan makes a remark Blake interprets as questioning the truth of his life story. Tensions escalate further when Morgan brings up Blake’s late wife, for whose murder he’d been acquitted. The actor becomes so enraged that his televised responses seem to feature more bleeps than actual words. The heated exchange, however, prompts Blake to overshare far beyond what he likely intended when agreeing to the interview. By the end, it felt like we’d not only read his memoir but also all the parts that didn’t make it into print.

1977
This marked the first time the Cuban leader had talked to an American journalist. Walters called him “charismatic—very charming and funny,” but that didn’t stop her from asking hard-hitting questions. She presses him on his politics and leadership and even tries to get some personal tidbits. Walters is relentless—she has a job to do, and no one, not even someone seen by some as a dictator, would get an easy pass. He holds his ground, staying true to his beliefs, as he famously did throughout his career. This is especially evident when asked about freedom of the press and democracy. He later called this interview one of the toughest he’d ever faced.

2021
Conversations about “how dark” their baby's skin tone would be. A rift between Prince Harry and his father so deep that Harry said his father at one point “stopped taking my calls.” And Meghan, Duchess of Sussex, opening up about how much the stress of it all had taken a toll on her mental health. These were some of the shocking details described by Harry and Meghan in an exclusive interview with Oprah Winfrey, the first they had given since they stepped away from official royal duties the previous year. They said they would have stayed had they gotten support from the royal family. Buckingham Palace responded to the interview by releasing a statement.

1995
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 misconduct 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.

2005
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.

2011
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.

2003
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.

1995
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 disordered eating, 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.

2013
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.

1988
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 Barbara 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.

2015
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.

1999
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.

1977
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.


Which celebrity interview hit you the hardest? Let us know in the comments.