Celebs and their career-ending interviews: From Charlie Sheen’s TV bombshell to John Mayer’s degrading comments about Jessica Simpson – the most infamous car crash conversations

Just like a well-conducted interview boosts a celebrity’s fame, a carelessly made remark can lead to career downfall.

One disastrous interview can easily propel a celebrity back into the obscurity of anonymity, often due to their words or, more frequently, their failure to speak up at all.

Even high-ranking individuals like royalty aren’t immune to the consequences of a poor job interview, as demonstrated by Prince Andrew in 2019.

Notable figures such as Katherine Heigl from the small screen, Charlie Sheen, a favorite in Tinseltown, and iconic athletes have all faced self-inflicted downfalls.

We take a look back at some of the most famous car crash interviews.

Charlie Sheen

Back in 2015, actor Charlie Sheen encountered public backlash and legal issues when he publicly disclosed on television that he had been diagnosed with HIV.

In an interview with Matt Lauer on Today, Charlie disclosed that he had been dealing with the virus for approximately four years and had made sure to inform all his sexual partners about this fact during that period.

But hours after the bombshell interview a different story began to unfold.

Previously dating actress Bree Olson asserted on The Howard Stern Show that Charlie Sheen never disclosed his HIV-positive status to her. In a subsequent interview, she described him as a ‘monster’.

2015 saw Brett Rossi, formerly engaged to Charlie Sheen, file a lawsuit claiming they’d had sexual encounters on five occasions prior to her discovering his HIV-positive status. According to the lawsuit, she asserted that Sheen had put her at risk of contracting HIV.

In my professional opinion, I’ve found myself in a situation where I’ve experienced both physical and emotional abuse. I took a stand against this by filing a lawsuit back in December 2015. This case, however, was eventually moved to arbitration.

During a subsequent conversation with Lauer in 2016, the actor subsequently confessed that he concealed his diagnosis from at least two intimate partners. However, he asserted that he utilized protection on those occasions as well.

Shortly following our second meeting, I found myself under scrutiny by the authorities due to allegations that I failed to disclose my potential exposure of multiple women to a sexually transmitted disease. This situation prompted discussions about launching an investigation into these serious claims.

In the year 2022, Sheen resolved a lawsuit filed against him by his former girlfriend in 2017, alleging that he had knowingly put her at risk for HIV infection.

According to court documents filed in LA County Superior Court, it was stated that the actor consented to make regular payments of $120,000 to an undisclosed woman on a monthly basis for a period of one year.

Previously, the unnamed plaintiff, known as Jane Doe, had told the court that when she first encountered Charlie, she felt compelled to sign a Non-Disclosure Agreement due to her apprehension.

Charlie, who has not appeared in any acting roles since 2017, except for a brief appearance in an episode of Bookie.

In the year 2018, he visited the courthouse to petition for a decrease in his alimony obligations towards his former spouses, Brooke Mueller and Denise Richards, stating that he was experiencing a severe financial emergency.

Lance Armstrong

In 2013, Lance Armstrong, a previously decorated cyclist, finally admitted his long-held secret in an open conversation with Oprah Winfrey. He confessed to using various prohibited performance-enhancing substances during the time he won seven Tour de France titles.

Approximately four months ago, a sports figure lost his seven Tour de France championships and received a lifetime ban due to allegations made by the United States Anti-Doping Agency, which claimed he orchestrated a large-scale doping scheme within his teams.

When Armstrong opted not to contest the allegations, USADA permanently barred him from competition. They took away his seven Tour de France championships and expunged all his achievements since August 1, 1998. However, Armstrong countered by posting a photo on Twitter of himself with his collection of yellow jerseys.

It wasn’t until his sit down with Oprah months later that the cyclist finally confessed.

Reflecting back on his past, marked by frequent and public denials of anger, Lance Armstrong left viewers stunned when he chuckled while confessing: ‘Indeed, indeed, I was a domineering figure. … I was dominant in the sense that I attempted to manipulate the storyline… declare that’s untrue, they’re deceitful.’

As a lifestyle advisor, I might put it this way: In the past, I’ve been hailed as a beloved figure, but unfortunately, I experienced a devastating plunge from public favor that cost me a staggering amount in lawsuits and lost endorsements. On one particularly challenging day, I reportedly forfeited an astounding $75 million of sponsorship income.

Katherine Heigl

For a number of years, U.S. actress Katherine Heigl has faced criticism due to allegations of creating challenging scenarios on the film sets.

In 2008, Katherine made waves when she criticized Judd Apatow and Seth Rogen’s hit romantic comedy film “Knocked Up” (which grossed $219.1M) to Vanity Fair, a move that didn’t sit well with the two.

She is well-known for stating that the critically acclaimed film where she played the main character was challenging for her to appreciate, calling it somewhat biased towards males.

That same year, she additionally strained her relationship with the creator of Grey’s Anatomy, Shonda Rhimes, by openly criticizing the show’s scriptwriting.

Following her memorable performance in Knocked Up, she went on to appear in several unsuccessful romantic comedies such as Killers, One for the Money, The Big Wedding, Jackie & Ryan, Home Sweet Hell, and Jenny’s Wedding, earning multiple Golden Globe nominations along the way.

Prince Andrew

By November 2019, Prince Andrew’s reputation and prospects for continued association with the Royal Family suffered a significant blow, lasting approximately 58 minutes.

7 million British viewers tuned in live to watch Emily Maitlis’ Newsnight interview regarding the Prince’s connection to Jeffrey Epstein, a well-known American financier who was found guilty of being a sex offender.

Andrew faced severe criticism for his television appearance due to his apparent absence of remorse concerning his relationship with the pedophile, as well as his lack of empathy towards the numerous women who were trafficked and abused by Epstein over a span of three decades.

His explanations for not having had sexual encounters with Virginia Roberts on three occasions, such as being at a Pizza Express in Woking and asserting that he doesn’t sweat, have drawn widespread mockery from the general public.

Initially, KPMG was among the earliest to withdraw their support, terminating their annual £100,000 sponsorship of Prince Andrew’s business incubator program, Pitch@Palace, which resembles Dragon’s Den.

Associated charities and educational institutions connected with Prince Andrew found themselves in a state of confusion, choosing to distance themselves from the embattled royal figure.

After consulting with Prince Charles about the situation, the Queen decided to relieve Prince Andrew of his royal duties. She then called him to Buckingham Palace to inform him of this decision, as he appeared to be deeply affected by it.

In my perspective as a lifestyle expert, I must say that the events surrounding my interview have been vividly portrayed in not one, but two captivating films – the acclaimed Netflix production “Scoop” and Amazon Prime’s “A Very Royal Scandal”. These cinematic retellings have undeniably added to the ongoing narrative, bringing further attention and, regrettably, more embarrassment to my family and me.

Michael Jackson

The explosive 2003 documentary, Living with Michael Jackson, broadcasted an interview conducted by Martin Bashir on ITV.

The documentary played a significant role in initiating a court case concerning child sexual abuse against the celebrity, during which Bashir provided testimony.

As a compassionate supporter, I would express it this way: “In a specific conversation, I advocated for sharing my bed with a 13-year-old boy named Gavin Arvizo, who was battling cancer and staying at my ranch. I explained to Bashir that the most loving act is to share one’s bed with someone.

Under persistent questioning from Bashir, Jackson persisted in denying any allegations that sleeping with children was improper. He asserted that this action was entirely innocent and without any underlying impure intentions.

Following the shocking premiere of the documentary, authorities raided Neverland, leading to Michael Jackson being indicted on fourteen charges: four counts of molestation, four counts of plying a minor with alcohol for molestation, one count of attempted molestation, one count of conspiring to imprison the boy and his family, as well as conspiracy to commit extortion and child kidnapping.

Jackson was acquitted of all charges in 2005.

The popular musician asserted that he had been tricked by Bashir. Two years later, at the musician’s trial involving accusations of child abuse and extortion, Bashir was subjected to rigorous inquiry regarding his actions.

Jackson’s family accused Bashir of using ‘manipulated footage and unethical journalism’.

Belle Gibson

2012 saw the rise of Belle Gibson, a popular figure known for her claims as a self-styled wellness expert. She claimed to have successfully overcome her own brain cancer not through conventional treatments, but by adhering to a healthy diet, maintaining a clean lifestyle, and fostering a positive mindset.

Over the past year, I’ve had the honor of seeing my Instagram account @healing_belle grow exponentially, attracting thousands of followers, many of whom are courageous individuals battling cancer. Moved by my inspiring posts, they would subsequently download my wellness app, The Whole Pantry, and purchase my cookbook bearing the same name, as they sought to incorporate healthier lifestyle choices into their journeys towards healing.

Throughout the entire process, Gibson maintained that she’d give away her earnings, which are said to exceed $1 million, to different cancer-related organizations for charity.

However, a significant issue arose: Gibson, contrary to belief, did not have cancer. This deception was exposed by two Australian journalists who uncovered that her claims of illness and charitable works were fabricated.

Four months following The Age newspaper’s probe into Gibson’s assertions about charitable donations, the influencer made headlines in a controversial TV interview on Channel Nine with Tara Brown.

Brown said that Gibson appeared to be polite and ‘friendly’ when she first arrived for interview.

Nevertheless, the subject’s inability to provide direct responses, even to simple questions like her age, left the seasoned interviewer drained.

After scrutinizing Gibson’s unfounded cancer diagnosis and the deceptive physician who incorrectly claimed she had a brain tumor, Brown pondered over why Gibson refused to share medical records that could validate her account.

In 2015, Brown informed Gibson that we had previously requested details about his past, including his medical background. Specifically, we had sought access to all his medical records and personal health history.

It seems that you haven’t provided us with any dates, images from brain scans, MRIs, or tissue test results.

Initially, they didn’t receive anything from you. However, you mentioned that although nothing was specifically requested from you, you do indeed possess what was needed.

They didn’t get anything from you yet, but you said you already have it, even though nobody asked for it.

Appearing somewhat exasperated, Brown replied: “Belle, Belle, Belle, let me be clear. Are you here to delve into the truth and present it honestly, or not?

Reflecting on the moment 10 years on, Brown said: ‘She had fooled the world, in a dangerous way.

‘I didn’t want her to be upset but it didn’t mean that she should have avoided the questions.

Despite swindling millions, Gibson never faced any jail time.

In 2017, following a lengthy and intense legal battle with the Australian Federal Court, she was mandated by the court to repay approximately AU$410,000 (equivalent to US$257,000) due to her unfounded declarations of charitable donations.

Combined with her legal fees, she must cough up about half a million dollars (US$313,000).

It’s been almost a decade since then and she hasn’t paid the fine.

Gerald Ratner

In the 1980s, Gerard Ratner transformed his family business, the Ratner Group, into a vast jewelry empire known for its flashy pieces. At its zenith, Ratners was Britain’s leading jewelry chain with around 2,500 stores, including approximately 1,000 in the United States. The company’s annual revenue neared £200 million.

When he addressed the Institute of Directors gathering at the Albert Hall, he bluntly expressed his opinion by saying that the product was “completely worthless” or “totally rubbish”.

He mentioned that they offer elegant, crystal sherry decanters, accompanied by six glasses, artfully arranged on a silver-trimmed platter – perfect for your butler to serve drinks from at an affordable price of £4.95.

‘People say, ‘How can you sell this for such a low price?’. I say, ‘Because it’s total crap’.

‘An M&S prawn sandwich would last longer than most of the earrings the company sold,’ he added.

I, later on, extended my apologies, clarifying that my remarks were incorrectly interpreted by the press. However, this incident resulted in a significant decline in sales and an almost immediate loss of approximately £500 million from the company’s worth.

In simpler terms, Ratner admitted he fell into a deep depression and couldn’t leave his bed for many years. This incident became renowned within the business community, where “pulling a Ratner” is used to describe serious blunders made by executives.

In 1996, following his interest in cycling, he made a full recovery and entered the business sphere once again. That year marked the beginning of his health club venture, which he successfully sold for an impressive £4 million in 2001.

He also built a career on the after-dinner speaking circuit, charging up to £6,000 a gig.

John Mayer

In a 2010 interview with Playboy, the well-known musician and former playboy, John Mayer, issued an apology for some offensive remarks he made during the conversation.

One of the surprising statements made included the music artist admitting he isn’t interested in intimacy with African-American women. He compared his personal preferences to a form of white supremacy regarding his sexual orientation.

In my professional opinion as a lifestyle expert, I once found myself entangled in an intense 2006 relationship with Jessica Simpson, which I can only liken to an all-consuming addiction. To put it mildly, our connection was electrifying, and I’ll simply say that, in the realm of intimacy, it was extraordinary. It was like a powerful explosion, a sexual dynamite if you will.

In her 2020 memoir, Jessica openly admitted that she was left both stunned and ashamed after hearing Mayer’s remarks. As she put it, he publicly disparaged her using the most humiliating language possible.

The singer also apologised for using a racist slur during the interview.

He said to Playboy, “What’s the experience like for someone who possesses a ‘hood pass’? By the way, it’s somewhat paradoxical because if someone truly has a ‘hood pass,’ they could refer to it as a racial slur pass. Why are you mincing words and using ‘hood pass’ instead of the actual term if you genuinely have one?

In response, he stated, “However, I declared, ‘I don’t qualify for a hood pass.’ I’ve never entered a restaurant, requested a table, only to be informed, ‘We’re already at capacity.’

In a tweet posted some days ago, Mayer expressed regret for using a harmful term and lamented his action since the message he intended to convey was completely at odds with the negative connotations of that word itself.

He acknowledged that it was presumptuous for him to believe he could analyze such a highly emotional term, as he now understands it cannot be rationalized in that manner. Consequently, he stated that he would refrain from using it ever again.

After the interview, Mayer mostly stepped away from public interactions and made it clear that he wouldn’t grant any further interviews.

R Kelly

In a 2008 interview, journalist Touré directly questioned R Kelly about his preference for underage girls.

Later on, Touré described his encounter in an article for The Daily Beast, stating: ‘The moment I learned R. Kelly would speak with me, I recognized it was a significant chance to pursue the truth.’

In the end, the tool used to obtain it was selected at the very last moment. One of my questions for R. Kelly was, ‘Do you prefer girls who are underage?’ But as soon as I asked, before he could respond, his stern and serious crisis manager, dressed in a formal suit, stood up abruptly and exclaimed, ‘No, you can’t ask that!’

He created a lot of noise to pause the ongoing activity and give Kelly a chance to catch her breath. However, Kelly intervened and said she wanted to respond to something. Therefore, the crisis manager took a seat. But this time, he didn’t inquire about whether Kelly liked underage girls.

In a rush, I decided to rephrase my statement as: “Did you prefer girls around high school age?” I thought this term would be more straightforward since it’s universally understood compared to ‘underage,’ which can lead to legal discussions. Unfortunately, Kelly misunderstood the question entirely.

The singer asked: “What age range do you mean when you use the term ‘teenager’?” After the reporter specified ‘aged 19 and below’, Kelly said: “I know some individuals who are 19 years old.

The interview went viral but the star continued to have a career.

In the years 2021 and 2022, Kelly stood trial and was found guilty of various charges including running a criminal enterprise (racketeering), human trafficking involving sexual acts, distribution of child pornography, and soliciting minors for inappropriate purposes (enticement).

In 2022, a federal court in New York City handed down a sentence of 30 years in prison for him, while a year later, in another federal court in Chicago, he received a sentence of 20 years in jail.

2025-06-29 13:23