Top 20 Famous People That Ruined Their Career With One Photo

#20: Perez Hilton

It would take a lot to get the harsh tabloid blogger Perez Hilton in trouble. But he went too far in 2010, just by posting on Twitter a censored upskirt photo of Miley Cyrus. She was still a minor and working for Disney at the time. Threats of criminal charges prompted Hilton to confirm that Cyrus was wearing underwear, and that the photo was meant to entice readers. Still, he made no apology for the deception or to the young popstar. The scandal quietly unraveled the loudmouth’s prevalence in the mainstream. Although Perez remains very active, this display of his unscrupulousness turned him from someone you love to hate into a pop culture villain.

#19: Sarah Idan

The Miss Universe pageant should represent the beauty in bringing cultures together. Of course, it’s hard enough to do so tastefully without Sarah Idan’s snafu. The Iraqi-American singer was representing her homeland in 2017 when she posted a photo of herself with Miss Israel, Adar Gandelsman. The caption read, “Peace and Love from Miss Iraq and Miss Israel.” This noble yet controversial comment, compounded by Miss Universe’s swimsuit competition, sparked an uproar in Iraq. Idan and her family were eventually forced to settle in the U.S., where her music career faded into obscurity. Thankfully, Idan has since found new work in entertainment and politics, and remains a staunch advocate for peace in the Middle East.

#18: Dani Mathers

Playboy Playmate of 2015 Dani Mathers already represented an unfair pressure on culture. There’s certainly no excusing her cruel insult in 2016. Mathers photographed a 71-year-old woman using a shower at an LA Fitness, then shared the image with a friend. It wound up on social media with a derogatory caption. Besides the backlash over body-shaming, the model was charged with unlawful invasion of privacy. She was ultimately sentenced to community service, hit with a restraining order, banned from LA Fitness, and forbidden to post photos without the subjects’ consent. She was also fired from her radio show and lost work. Years after doing her time, Mathers remains professionally ostracized for her truly ugly behavior.

#17: Matt Hancock

Personal scandal is bad enough for politicians without it directly contradicting the office’s responsibilities. Matt Hancock was burdened with the role of the UK’s Secretary of State for Health and Social Care during the COVID-19 pandemic. In 2021, his work was overshadowed by a CCTV still of him kissing Gina Coladangelo, one of his advisers, in his office. The revelation of their extramarital affair, never mind their violation of social distancing guidelines, forced both public health officials to resign. Many of Hancock’s colleagues then came forward about his inefficiency and hypocrisy in his highly important position. He and Coladangelo have since left their respective spouses to make their relationship official. Still, it’s haunted by an image that especially derailed Hancock’s political career.

#16: Millard Tydings

In his four terms as a U.S. Senator from Maryland, Millard Tydings gained a reputation for his outspokenness. His stand against McCarthyism would ultimately be his downfall. When Tydings brought this into his re-election campaign in 1950, Senator Joseph McCarthy’s staff released an old photo of the Democrat being friendly with Communist Party leader and Soviet spy Earl Browder. Testimonies and an investigation eventually revealed that the photo was a composite, and that Tydings had never met Browder. Nonetheless, the scandal is credited with costing him the election against strident anti-communist John Marshall Butler. Tydings died a pariah 11 years later, representing one of the earliest and cruelest injustices of the Second Red Scare.

#15: Paul Reubens

Comedian Paul Reubens won hearts of all ages as the zany Pee-wee Herman. All that stopped in 1991, when he was arrested for indecent exposure at an adult movie theater. The scandal alone was enough to destroy the beloved family entertainer. But there was no unseeing his mug shot for the Sarasota County Sheriff’s Department after the press got ahold of it. The long, unkempt hair and disgraced expression couldn’t have been further from Pee-wee’s clean and happy-go-lucky image. Reubens was exiled for years, and revived his career with more mature projects until his passing in 2023. Still, he’s forever associated with one of the ‘90s’ most shocking entertainment scandals, immortalized by that career- and childhood-ruining mug shot.

#14: Peter Norman

People often overlook the subtler gesture in one of the most important images in sports history, as well as its consequences. At the 1968 Summer Olympics, Peter Norman of Australia came in second in the 200-meter running event behind Tommie Smith. He and fellow American John Carlos then became global icons of the civil right movement by striking the Black Power stance during the medal ceremony. Beside them, the white Norman dons a badge representing the Olympic Project for Human Rights in solidarity. It’s understood that this political act stifled his career back home. Even with his qualifications, he wasn’t selected for the ‘72 Olympics. Australia now recognizes Norman as a national hero for unimposingly standing up for what’s right, whatever the professional cost.

#13: Michael Phelps

The most decorated Olympian of all time has long struggled with alcohol use disorder. But it was a different substance that nearly ruined Michael Phelps’s swimming career. In 2009, the tabloid News of the World published a photo of him smoking marijuana at a party at the University of South Carolina. This resulted in a three-month suspension and cost him a coveted sponsorship deal with Kellogg’s. The professional penalties were really not that severe, but Phelps’s reputation really took a hit. The scandal became ubiquitous in pop culture, hanging over the public figure’s status as his personal life garnered further controversy. It’s hard to believe that such a celebrated athlete may never completely outpace this scandal.

#12: Chris Brown

R&B fans once considered Chris Brown and Rihanna the dream celebrity couple. Then they saw the extent of the former’s volatile behavior. In 2009, TMZ acquired a police photo of Rihanna’s face after a vicious assault by Brown. The circulation of this image of the beauty icon sparked a debate about the media’s right to share such graphic details. But there was no debate about her ex-boyfriend’s reputation. Brown’s career and music were permanently associated with this visual of his abusive tendencies. He pleaded guilty to the assault and underwent domestic violence counseling, but has since faced many more ghastly scandals. It’s unlikely that said R&B fans would forgive him after seeing that photo of Rihanna anyway.

#11: Prince Andrew

A distinguished naval career and philanthropic businesses made Prince Andrew a star in the British Royal family. Then, in 2011, Mail on Sunday published a 2001 photo of the Duke of York with his arm around a teenaged Virginia Giuffre. This marked the beginning of the human trafficking survivor’s fight against the woman in the background, Ghislaine Maxwell, and the photographer Jeffrey Epstein. Andrew spent the next 11 years dealing with scandal, legal battles, and fallout from a misguided interview with “Newsnight” in 2019. Finally, he was stripped of all royal duties and exiled from the public eye. If the late Giuffre’s accusations and the implications of that photograph are true, that is nowhere close to true justice.

#10: Kate Moss

British supermodel Kate Moss built her career appearing in prestigious fashion campaigns and iconic magazine covers. However, in 2005, Moss made news for all the wrong reasons when the Daily Mirror ran front-page pictures of her engaging in substance use, alongside a damning headline. This publication ignited a major controversy, resulting in Moss being dropped by major fashion brands, including Chanel, Burberry and H&M, with whom she held an estimated £4 million annual contract. She was even investigated by the London Met police, although all charges were eventually dismissed. The damage to her career may have been extensive, but Moss managed to weather the storm, bouncing back to the forefront of the industry in a matter of months.

#9: Chris Lee

While the damning picture in this case may pale in comparison to the others on the list, it nonetheless marked the end of this politician’s career. In February 2011, a few months after winning reelection in a landslide, New York congressman Chris Lee got ensnared in a scandal when it was revealed that he had solicited a woman on Craigslist. Despite being married, Lee had sent the woman a shirtless photograph of himself flexing his muscles and falsely portrayed himself as a divorced lobbyist. This picture, as well as the messages the two exchanged, eventually got leaked to the website Gawker. Within hours of their release, Lee issued a public apology and resigned his congressional seat.

#8: Bow Wow

If you ever needed a reminder not to trust everything on social media, this would be it. In May 2017, Bow Wow shared a picture that appeared to capture a typical day in the life of a celebrity. The post showed a luxury car parked beside a private jet on an airport tarmac, suggesting he was about to embark on a lavish trip. Initially, no one thought much of it, until hours later, when another picture emerged showing the rapper seated in economy class on a commercial flight. Eagle-eyed fans quickly traced the original picture to the website of a VIP transport company. The gaffe sparked widespread ridicule on social media, and portrayed Bob Wow as a very dishonest individual.

#7: Ed Miliband

Throughout history, several politicians have ruined their careers for a variety of shocking reasons – corruption scandals, sex scandals, bigotry. However, for British politician Ed Miliband, his downfall came from a simple act many of us engage in daily: eating a sandwich. Back in 2014, while campaigning for local elections, Miliband, then Labour Party leader, was photographed eating a bacon sandwich. Granted, almost anyone would look awkward if caught mid-bite, but Miliband’s depiction was particularly cringe-worthy and quickly invited widespread ridicule. As the 2015 general election approached, the image resurfaced on the front page of the tabloid The Sun, effectively overshadowing any substantive policies with mockery. Needless to say, Miliband lost the election and resigned as the Labour Party leader shortly after.

#6: Gary Hart

Rarely ever has a promising presidential bid crashed and burned as quickly as Gary Hart’s. Hart was the frontrunner for the Democratic presidential nomination in 1988, but his campaign was plagued by rumors of extramarital affairs. He vehemently denied these allegations, even challenging the media to follow him around and prove them. Well, they did, in fact, accept his challenge. The press linked Hart to Donna Rice, a young woman seen spending the night at his house. Even worse, they unearthed a damning picture of Rice sitting on Hart’s lap, with him wearing a shirt referencing a yacht they had partied on, aptly named Monkey Business. It didn’t take long for Hart to suspend his campaign and drop out of the race.

#5: Mike Dukakis

Following Gary Hart’s withdrawal from the 1988 primaries, Democrats ultimately chose Massachusetts Governor Michael Dukakis as their nominee. Despite running an impressive primary campaign, Dukakis’ abysmal bid for the White House was met with a resounding defeat. This was due to various shortcomings, notably the now infamous tank photo. Having been portrayed by Republicans as weak on crime and defense issues, Dukakis sought to bolster his tough image by posing in a military tank. However, this backfired spectacularly as the photograph, depicting Dukakis in an oversized helmet with his name splashed across, was exploited by his opponent and widely ridiculed. Today, even Dukakis himself concedes that the tank photo was a huge misstep.

#4: Vanessa Williams

In September 1983, Vanessa Williams made history as the first African-American to win the Miss America title. She fulfilled her duties gracefully until, just before the end of her reign, it was revealed that explicit images of her would be published in Penthouse magazine. The pictures were taken in 1982 when she worked as an assistant for a photographer, who led her to believe they had been destroyed. Even before their publication, the Miss America Organization pressured Williams to resign, subsequently awarding the title to the first runner-up. Williams faced severe ridicule in the media and, for a while, it seemed her career was over. Nevertheless, she managed to rebound, establishing a successful career as a versatile entertainer.

#3: Al Franken

He first gained recognition as a comedy writer and cast member on “Saturday Night Live,” but it appears sometimes, Al Franken’s jokes might cross certain boundaries. While serving in the U.S. Senate in 2017, Franken faced accusations of sexual misconduct from radio broadcaster Leeann Tweeden. These allegations gained further traction when a compromising photograph emerged, showing Franken with his hands positioned above Tweeden’s breasts. According to the Senator, this was intended as a joke. While the accusations were still being investigated by the Senate Ethics Committee, several Democratic senators called for Franken’s resignation. He ultimately succumbed to pressure and stepped down from the Senate, a decision he now regrets.

#2: Anthony Weiner

Some people just never learn from their mistakes. Anthony Weiner represented New York's 9th congressional district and was viewed by some as a rising political star. However, in 2011, Weiner dug himself into a hole and never found his way out. The congressman used his public Twitter account to share a link to a suggestive picture of himself, but initially denied responsibility. Faced with insurmountable evidence, he confessed and resigned from office. Yet, this wasn’t the end of Weiner’s troubles. He resurfaced to run for New York City mayor in 2013, but encountered another setback due to yet another sexting scandal. In 2017, he was implicated in a third scandal, ultimately receiving a 21-month prison sentence for engaging in explicit communication with a minor.

#1: Kathy Griffin

Donald Trump has divided public opinion ever since he first announced his presidential candidacy in June 2015. But nearly everyone came together in condemnation of this horrifying stunt. In May 2017, months after Trump’s inauguration, comedian Kathy Griffin posted a graphic image online, in which she held a bloody mask that closely resembled the then-President. The backlash was immediate. Criticism filtered in from both sides of the political divide. As a result, Griffin took the picture down and apologized. But the damage was already done. She lost multiple business deals, was fired by CNN, and had to cancel her upcoming tour dates. Griffin eventually retracted her apology and reposted the controversial photo on the day after the 2020 presidential election.

What are some other photos that incriminated celebrities in the court of public opinion? Break the story in the comments.