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10 Tragic Interviews Because of What We Know Now

10 Tragic Interviews Because of What We Know Now
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VOICE OVER: Tom Aglio
These interviews take on a whole new meaning with hindsight... Join us as we examine conversations that now break our hearts because of what happened after. From Princess Diana's manipulated Panorama interview to Chadwick Boseman's emotional moments while secretly battling cancer, these exchanges reveal painful truths about celebrities whose struggles went deeper than we knew. Our countdown includes Chester Bennington's hopeful radio appearance weeks before his death, Britney Spears being reduced to tears by Diane Sawyer, early signs of Bruce Willis' cognitive decline, and Stephen "tWitch" Boss appearing vibrant just days before his tragic passing. Which of these heartbreaking moments affected you most? Let us know in the comments below!

Princess Diana

Panorama (1953-)


In 1995, Princess Dianas BBC Panorama interview stunned the world. Speaking with journalist Martin Bashir, the interview painted a picture of a woman caught in a toxic institution. Diana revealed the breakdown of her relationship, famously stating, There were three of us in this marriage. However, years later, it was revealed that Bashir had used deceitful tactics to secure the chat, including tricking the Princess of Wales with falsified bank statements. It was a clear example of the relentless media obsession with Dianas private life - made all the more tragic by the fact that she would lose her life nearly two years later while being pursued by the press.


Chester Bennington

102.7 KIIS FM


Just weeks before he tragically took his own life, Linkin Park frontman Chester Bennington gave a revealing interview with 102.7 KIIS FM. In the chat, he talked about how making music helped him through dark times, and reflected on inner struggles even saying, I find myself getting into these patterns of behavior. Despite his openness, Chester also maintained a hopeful tone - one that made his passing shortly after all the more devastating. The interview shows a man still trying to fight and still trying to heal. In hindsight, its a heartbreaking final glimpse of someone who gave so much to others while fighting demons of his own.


Britney Spears

Primetime (1989-2012)


In 2003, a 21-year-old Britney Spears sat down with Diane Sawyer for a primetime TV interview that has since aged like milk. Sawyer grilled Britney about her breakup with Justin Timberlake, accused her of being a bad role model, and even relayed a statement by the then-First Lady of Maryland saying she should be shot. Britney, visibly distressed in moments, broke down in tears. At the time, this was seen as tough journalism. Now, in the wake of the #FreeBritney movement and greater awareness of her troubled past, this interview feels exploitative and cruel not to mention interrogative.


Bruce Willis

The One Show (2006-)


In a 2013 appearance on BBCs The One Show, Bruce Willis appeared confused and disengaged, struggling to answer basic questions. At the time, the interview was seen as bizarre, with critics labeling Willis aloof or uninterested. However, in light of his 2022 diagnosis with aphasialater revealed to be part of frontotemporal dementiathe moment now feels deeply tragic. What once seemed like awkward rambling now appears to be an early sign of a devastating cognitive decline. Rather than a celebrity phoning it in, the interview shows a man quietly battling symptoms of a disease that was already affecting his ability to communicate.


Corey Feldman

The View (2013-)


When Corey Feldman appeared on The View in 2013, the Stand By Me actor spoke openly about the mistreatment he and fellow child star Corey Haim allegedly endured in Hollywood. While Feldman was visibly emotional and serious, The Views panelists - particularly Barbara Walters - responded with skepticism. Walters even responded to his claims by saying, Youre damaging an entire industry. Today, Coreys warnings are viewed with far more gravity, especially in the wake of the #MeToo movement and increased scrutiny of child exploitation in the entertainment world. To this day, he remains a steadfast voice for victims of child abuse and neglect.


Mariah Carey

The Ellen DeGeneres Show (2003-22)


The Ellen DeGeneres Show was often billed as a lighthearted space full of laughter and games. But, in a 2008 appearance on the Emmy-winning daytime talk show, Mariah Carey found herself in a painfully uncomfortable situation. Amid swirling pregnancy rumors, Ellen offered the singer champagne on-air, trying to pressure her into confirming whether she was expecting or not. Clearly uneasy, Mariah awkwardly declined and attempted to laugh it off. It wasnt until later that she revealed she had tragically suffered a miscarriage shortly after the appearance. Today, the clip is widely seen as invasive and inappropriate not to mention cringeworthy.


Stephen tWitch Boss

The Jennifer Hudson Show (2022-)


Stephen tWitch Boss sadly took his own life in December 2022 at 40-years-of-age. However, the beloved DJ from The Ellen DeGeneres Show had made a public television appearance just days before his death. In an interview on The Jennifer Hudson Show, Boss appeared radiant - joking with host Jennifer and speaking excitedly about upcoming holiday projects. He showed no visible signs of distress, making the shock of his passing all the more devastating. The disconnect between his vibrant presence and his internal pain only underscores how invisible mental health struggles can truly be.


Amy Winehouse

Friday Night with Jonathan Ross (2001-10)


Amy Winehouse gave several interviews that feel tragically revealing in hindsight, but her 2004 appearance on Friday Night with Jonathan Ross stands out as one of the most heartbreaking. It was a moment of celebration for Amy as she was promoting her first studio album and was already being hailed as a powerhouse rising star. But even in this relatively early appearance, Amy seemed uncomfortable and guarded, brushing off questions and giving answers laced with nervous laughter. Her perceived withdrawn demeanor, in retrospect, showed the beginning of a troubled life fueled by addiction and personal turmoil. Years later, Amy would die from accidental alcohol poisoning at the age of 27.


Melissa Benoist

The Tonight Show Starring Jimmy Fallon (2014-)


When Supergirl star Melissa Benoist appeared on The Tonight Show Starring Jimmy Fallon in 2016 and told a quirky story about a household mishap, nobody thought anything of it. You see, Melissa explained how shed tripped down the stairs and injured her eye after colliding with a potted plant. But, years later, the truth behind that moment came to light. In 2019, Benoist bravely revealed she was a survivor of domestic violence, detailing an incident where a phone was thrown at her face, causing the same eye injury. In such, the story she told on Fallon was likely a cover, crafted to hide the tragic truth.


Chadwick Boseman

Sirius XM


When Chadwick Boseman was diagnosed with stage III colon cancer in 2016, he chose to fight the battle privately. Over the next four years, while undergoing countless surgeries and chemotherapy, Boseman brought Black Panther to life, turning the character into a global symbol of strength. What makes his journey even more extraordinary - and heartbreaking - is that he never let on in any of his interviews. One especially poignant instance came in 2018 when Boseman grew tearful recalling two young fans with terminal illnesses who were holding on to see his Black Panther film. Knowing now that he, too, was silently fighting for time adds a devastating layer to this heart-string-tugging moment.


Which of these interviews hit you the hardest? Let us know in the comments below.

tragic celebrity interviews heartbreaking celebrity moments Princess Diana Panorama Chester Bennington final interview Britney Spears Diane Sawyer Bruce Willis dementia signs Corey Feldman abuse allegations Mariah Carey Ellen pregnancy tWitch Boss Jennifer Hudson Amy Winehouse Jonathan Ross Melissa Benoist domestic violence Chadwick Boseman cancer battle celebrity mental health media exploitation
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