Joshua Goldman
Joshua Goldman
min read · June 29, 2025 · Entertainment

Star-Studded Disaster: The Most Infamous Interview Fails in Celebrity History

In 2015 actor Charlie Sheen faced outrage and lawsuits after revealing to Matt Lauer on Today that he was HIV-positive

CELEBRITY CAR CRASH INTERVIEWS: WHEN STARS GO WRONG

In the world of showbiz, a single interview can either catapult a celebrity to stardom or send their career spiraling down the drain. And when it comes to making a mess, some A-listers take the cake. From TV stars to Hollywood heartthrobs and even royalty, we've seen it all. Join us as we revisit some of the most infamous interviews that left audiences gagging.

CHARLIE SHEEN: HIV TRUTH OR LIE?

In a follow up interview with Lauer in 2016 the actor backtracked and admitted that he had hidden the diagnosis from at least two sexual partners

In 2015, Charlie Sheen sat down with Matt Lauer on Today to reveal he was HIV-positive. But hours later, his ex-girlfriend Bree Olson appeared on The Howard Stern Show, claiming he never told her about his diagnosis. The drama didn't stop there – a lawsuit followed, alleging that Sheen exposed multiple women to the virus without warning them. The actor's subsequent interviews only added fuel to the fire. Sheen eventually settled with one of the accusers for $120,000 and has been largely absent from the public eye since.

LANCE ARMSTRONG: FROM TOUR DE FORCE TO TOUR DE FRAUD

In 2013, Lance Armstrong confessed to Oprah Winfrey that he had used performance-enhancing drugs during his cycling career. But before that bombshell interview, Armstrong was stripped of his seven Tour de France titles and banned from the sport for life. The cyclist's downfall was a spectacular one – he lost an estimated $75 million in sponsorship deals and endorsements. The world watched as Armstrong went from hero to zero.

Decorated cyclist Lance Armstrong ended years of denials with a tell-all interview to Oprah Winfrey in 2013, confessing that he used a litany of banned substances

KATHERINE HEIGL: ROM-COM ROYALTY TO REPUTATION RUINER

In 2008, Katherine Heigl blasted Knocked Up, the romantic comedy she starred in, telling Vanity Fair it was "a little sexist." The actress also dissed Grey's Anatomy creator Shonda Rhimes, saying the show's writing was subpar. Heigl's comments sparked a firestorm of criticism, and her subsequent film choices only added to the controversy. Her once-promising career has since stalled.

PRINCE ANDREW: ROYAL RAP SHEET

Katherine Heigl famously upset Judd Apatow and Seth Rogen (pictured with Heigl in the movie) after badmouthing their critically-acclaimed romantic comedy Knocked Up

In 2019, Prince Andrew's disastrous interview with Emily Maitlis on Newsnight left his reputation in tatters. The Duke of York's inability to express contrition for his friendship with convicted sex offender Jeffrey Epstein and lack of sympathy for the victims sparked widespread outrage. His alibis, including a claim that he can't sweat, were ridiculed by the public. The fallout was severe – KPMG pulled its sponsorship of Prince Andrew's entrepreneur scheme Pitch@Palace, charities distanced themselves from him, and he was forced into retirement.

MICHAEL JACKSON: THE KING OF POP'S PUBLICITY NIGHTMARE

In 2003, Martin Bashir's documentary Living with Michael Jackson aired on ITV, featuring the pop star's controversial sleepovers with young boys. The fallout was catastrophic – Jackson faced child sex abuse allegations and was acquitted in 2005. His reputation never recovered.

Emily Maitlis' Newsnight interview about the Prince Andrew's relationship with Jeffrey Epstein, the American financier and convicted sex offender was watched live by 1.7 million Britons

BELLE GIBSON: WELLNESS WIZARD'S FALL FROM GRACE

In 2012, lifestyle influencer Belle Gibson rose to fame for her natural health remedies. But after telling a series of lies about her charitable donations, she was ordered by the Federal Court of Australia to pay AU$410,000 (approximately US$257,000). Despite owing half a million dollars in legal fees and fines, Gibson remains unrepentant.

GERALD RATNER: JEWELRY KING'S CRISIS OF FAITH

Martin Bashir's interview with Jackson was aired in the explosive 2003 documentary Living with Michael Jackson on ITV

In 1991, Gerald Ratner delivered an infamous speech at the Institute of Directors, telling a packed Albert Hall that one of his company's products was "total crap." The fallout was severe – sales plummeted, and Ratner's reputation was left in tatters. He later turned to after-dinner speaking, charging up to £6,000 per gig.

JOHN MAYER: PLAYBOY'S PUNCHLINES

In 2010, John Mayer sat down with Playboy for an interview that would haunt him forever. The pop star made a series of derogatory comments about women, including using a racial slur and declaring he was not open to having sex with black women. The backlash was swift – Mayer apologized and largely withdrew from public life.

Lifestyle influencer Belle Gibson gave an infamous TV interview with Channel Nine journalist Tara Brown on 60 Minutes Australia in 2015

R KELLY: THE KING OF R&B'S CRIMINAL PAST

In 2008, journalist Touré asked R Kelly whether he liked underaged girls. Kelly's response – "I have some 19-year-old friends" – sparked outrage. The singer was later convicted of racketeering, sex trafficking, child pornography, and enticement, earning a combined prison sentence of 50 years.

From Charlie Sheen's HIV controversy to R Kelly's criminal past, these celebrity car crash interviews are a reminder that even the brightest stars can fall victim to their own egos. Stay tuned for more juicy gossip and behind-the-scenes drama on TheScholarlyNote.com!

After a drawn-out and dramatic case against the Federal Court of Australia, she was ordered by the court in 2017 to pay AU$410,000 (US$257,000) for her false claims of charitable donations

Gerard Ratner built his family business Ratner Group into an empire of bling in the 1980s but Mr Ratner's humour became his undoing in April 1991

Singer and notorious playboy John Mayer apologised after make a string of derogatory comments about his ex Jessica Simpson in a 2010 interview with Playboy

Among the shocking comments was the popstar's declaration that he was not open to having sex with black women, describing his penis as 'sort of like a white supremacist'

During a 2008 interview journalist Touré asked R Kelly point-blank whether or not he liked underaged girls