Top 20 Most Heartbreaking Celebrity Interviews

Most people know this actor as the hilarious Chandler on “Friends,” but few of them were aware of his behind-the-scenes woes. In this ABC interview with Diane Sawyer, Matthew Perry was especially candid when describing his alcohol use disorder and prescription drug dependency. Along with revealing the medical emergency that served as a serious wake-up call, the actor told Sawyer about the decisions that threatened his life and career. In hearing everything that he’s been through, viewers will no doubt come away with an appreciation for his vulnerability and openness.

It should be obvious, but it isn’t always; regardless of a person’s social standing or professional status, mental health struggles can affect anyone. In 2018, supermodel Gisele Bündchen brought to light the difficulties of living with anxiety. The interview delved into her personal battle with panic attacks and negative thinking patterns. In the most heartbreaking moment, Bündchen teared up as she came to grips with her past. You could tell that she’d been through so much just by her tone of voice and delivery. Anyone thinking that she’s had a perfect life just because of appearances will have a change of heart after seeing her on “Access Hollywood.”

Considering her life’s work, Terri Irwin, the widow of the late Steve Irwin, has done so much for the world of conservation efforts and rehabilitation. She mentioned in a 2018 interview that she hadn’t quite moved on from her husband’s passing. Given the unique way everyone processes loss, her reaction is completely understandable. The nature of Steve’s death was also very sudden which, unsurprisingly, only caused additional heartbreak. Irwin refers to her husband as her soulmate and, if you’ve ever heard the story of their meetcute, you’ll probably agree. It, of course, only makes the whole story that much sadder.

In a special one-on-one interview on “The View,” Billy Crystal joined host Whoopi Goldberg to talk about his career and their mutual friend, Robin Williams. Both performers were clearly and justifiably shaken up by Williams’ untimely passing. Reminiscing about the past, Crystal shared many fond memories of their time in comedy together and expressed his inability to properly categorize or eulogize the “Good Will Hunting” star. The interviewee and presenter also shared a moving moment of silence for Williams. It’s completely devastating even today; we can’t imagine how difficult it was to watch for audiences at the time that it aired.

Naturally funny in anything he does, David Spade brought the very same energy to this “Good Morning America” segment. He spoke about his book and threw in a few jokes before the interviewer mentioned his sister-in-law, Kate Spade, who had taken her own life just a month before this interview. The loss clearly took its toll, and he thanked Robin Roberts for the tribute to his relative. It was a brief and subtle moment that revealed the obvious love he holds for his family. The performer also showed that it’s okay to both grieve and celebrate loved ones after death.

In a rare discussion about her health, the Canadian singer divulged the devastating effects she experienced as a result of Lyme disease. She went into detail about her illness in a profile that couldn’t be more heartbreaking. Reliving doctor visits, the star became emotional as she described the medical community’s confusion over her symptoms. The segment also referenced the fan support for her through one of her lowest moments. After seeing all of the people sending positive thoughts to Lavigne, you might end up crying along with her. Her perseverance through it all made for a moving story and an eye-opening interview.

In an interview from “The Me You Can’t See,” the artist described the awful events that transpired in her teenage years. These included being propositioned and assaulted by a member of the music industry. While discussing her PTSD diagnosis, Lady Gaga brought into focus the longstanding effects of her trauma and said she was still not comfortable identifying her abuser. It’s almost too overwhelming to watch, but Gaga didn’t hold back in her honest portrayal of events and the reaction she had. Ultimately, she shared her story as a part of her own healing process and in order to promote an open dialogue about these sorts of crimes.

After receiving a terminal diagnosis, singer Warren Zevon appeared on the “Late Show with David Letterman” to perform. He was largely in good spirits considering that he was dealing with a serious bout of lung cancer. Willing to talk about his health and even make a few light jokes, Zevon drew us in with his genuineness and what seemed to be complete and total acceptance of his situation. Before providing a farewell performance, the songwriter also gave some great advice to the audience about life. It’s the kind of candid moment that rarely happens on late night television.

Many people know Stephen Colbert as a funny talk show host. For this interview with Anderson Cooper, the comedian sheds his usual persona for a much more grounded conversation. Each man talks about the tragedies of their lives, and we get to hear Colbert speak on the tragic loss of his father and brothers. His philosophy on grief ends up being an enlightening moment that transcends the typical TV conversation. Cooper is taken aback by the poetic words, underscoring the powerful message at the heart of this discussion. By the end, it’s just wonderful to see two men talk about losing loved ones in such a frank and vulnerable interaction.

While talking about the impact of “Black Panther,” Chadwick Boseman discussed the impact of the film on fans. The performer choked up as he talked about two young cancer patients he was in contact with while filming. He put himself in the shoes of a child looking forward to something and really deeply commiserated with them. Knowing now that Boseman was himself battling the disease and kept it a secret, it’s difficult to imagine the depth of his feelings at that moment. He took an extended pause to collect himself in a moving display of emotions and it’s enough to bring us all to tears.

In an emotionally-raw interview with National Geographic, the American actress and filmmaker was asked about the moments and people that made an impression on her over the years. In response, Jolie related her first humanitarian trip to Sierra Leone and her encounter with a 10- or 11-year-old at a transit center with a gunshot wound that rendered him unable to move his legs. Being one among thousands, and considered a hopeless case, he was left untreated. Tearing up, Jolie recalled feeling completely helpless, but also how it helped her realize that every individual counts.

In this brutally honest interview, viewers had the chance to see a very different side of the rapper and songwriter. Kendrick Lamar has enjoyed tremendous success in his career, with no fewer than 13 Grammy Awards to his name. But in this MTV interview, he opened up about experiencing depression and suicidal thoughts, both on tour and at home. Delving into his darkest moments and how they’ve affected him, Lamar spoke soberly about how music became his therapy, and about feeling a sort of survivor’s guilt over his success - particularly after the murder of three close friends.

When she was just 14 years old, this American actress and author had to deal with the sad reality of coming home to find her parents gone. In an interview on CNN, Guerrero revealed how her parents tried to prepare her for the possibility that they could be deported, and her memories of the day it finally happened. Although many years have passed since the day Guerrero hid under her bed hoping that the police wouldn’t come for her too, some of the saddest moments in this CNN interview came when she revealed that, although she now sees them yearly, she still sometimes feels as if she doesn’t really know them anymore.

In a tear-jerking interview with “The Today Show’s” Matt Lauer, beloved actor and comedian Tracy Morgan told all. After a horrifying car accident that left him in a coma, Morgan woke up to discover that his close friend and mentor James McNair had been killed in the crash. Afterwards, Morgan confessed, he would watch the accident and McNair’s funeral on YouTube repeatedly until he “lost it.” Morgan also spoke freely about how the accident affected him physically, confessing to Lauer that he still suffers from memory loss, headaches, and nosebleeds.

In a series of intense interviews with the royal couple, ITV’s Tom Bradby revealed a lot going on under the surface. Prince Harry spoke emotionally about his trauma over the death of his mother, and his pain at the constant mistreatment his wife experiences. But it was even more heartbreaking to hear from the Duchess of Sussex herself. In a telling interview, Markle talked about her struggles with the British tabloids, especially as a newlywed and new mother. You can’t help but feel for the Duchess, who’s clearly feeling vulnerable, as she reveals that she is not really “okay.”

At 21 years old, this best-selling teenage artist of all time sat down with Diane Sawyer in 2003 for a tell-all interview. Sawyer certainly didn’t pull any punches. Things got noticeably difficult for Spears when Sawyer brought up her recent breakup with Justin Timberlake - who, Spears said, she imagined she would spend the rest of her life with. Although she admitted that Timberlake was “not wrong” in accusing her of being unfaithful, Spears couldn’t hold back the tears when his name came up, and begged for the interview to stop.

Although she never broke down in tears, the emotion was palpable in the face of the award-winning Barbadian singer and actress. In her interview with Oprah, Rihanna revealed that although she and her former flame Chris Brown were not in a relationship anymore, he was her first love and will probably always be the love of her life. In a particularly touching moment that will resonate with anyone who’s ever had to end things with someone special, she confessed that she’d be crushed if he is ever lonely or unhappy, and that she just wants him to be at peace.

Shortly after Ariana Grande’s concert ended in Manchester on May 22, 2017, a terrorist attack hit the arena, causing multiple deaths and over 500 injuries. In a subsequent interview with Beats 1 radio station, Grande was asked to talk about her song “Get Well Soon,” created as a response to the anxiety and trauma she experienced after the attack. She relived much of those raw emotions in the interview, as she discussed the song’s deeper meaning. As the title suggests, “Get Well Soon” is all about being there for one another - the musical equivalent of a hug.

Although Dion has given a lot of emotional interviews, there are perhaps none as heartbreaking as this unaired clip from “The Sunday Project.” In it, Dion recalled her last conversation with her husband René Angélil - a quiet phone call in her dressing room in which he told that her he loved her and wished her a good show. She also related going home that night after her concert and not going in to see him before his passing, a decision that has clearly weighed heavily on her.

The life of Lady Diana reads like a Greek tragedy, culminating in the devastating car accident that claimed her life in August 1997. Especially in hindsight, there’s something particularly heart-rending about her BBC1 Panorama interview, broadcast in November 1995. In it, she chronicled the struggles of living in the royal family, dealing with an unfaithful spouse, and living with constant public criticism and media attention. Although she didn’t feel like she would ever be queen, all she wanted was to be a “queen of people’s hearts,” and that’s the part that gets us every single time.