Halloween costumes are supposed to end up in a closet, but Billie Eilish and Jesse Rutherford’s 2022 couples look was built for permanent screenshots. Eilish, then 20, dressed as a baby while the 31-year-old Rutherford added wrinkles and a bald cap, apparently answering criticism of their age gap by turning it into the entire joke. Both were adults, and one costume cannot diagnose a relationship; it can, however, make the conversation spectacularly harder to escape. They split amicably in May 2023, leaving behind one remarkably committed visual punchline. | © Billie Eilish
Alexis Carter thought she was paying tribute to Rihanna when she recreated the singer’s Alexandre Vauthier jumpsuit for her 2014 prom. Instead, photos of the 16-year-old spread under the nickname “PromBat,” and Rihanna joined the pile-on by sharing mocking comparisons—including one placing Carter beside the Wu-Tang Clan logo. Carter later said she felt humiliated, discarded her Rihanna CDs and wanted an apology from her former idol. Celebrity Twitter was unusually lawless in that era, but an online mob hardly needed an assist from one of the world’s biggest pop stars. | © Getty images
America’s Next Top Model somehow booked the same indefensible concept twice. In 2005 and again in 2009, contestants were given makeup and styling intended to make them appear as ethnicities other than their own, producing images widely condemned as blackface. Tyra Banks acknowledged in 2020 that the series had made some “really off choices,” while the 2026 documentary Reality Check revived the debate after creative director Jay Manuel said he had asked to be excused from the first shoot. Calling it fashion experimentation became considerably less convincing once the experiment received a sequel. | © 10 by 10 Entertainment
Before Jimmy Kimmel became late-night television’s stern voice on politics and public decency, he repeatedly darkened his skin to impersonate NBA star Karl Malone. The late-1990s comedy bits leaned on an exaggerated voice as heavily as the makeup, making them difficult to file under harmless celebrity mimicry. Kimmel apologized in 2020, explaining that he once regarded the character as an impression rather than an imitation based on race, and admitted he had waited too long to address it. Personal growth may explain the distance between those two Kimmels, but it cannot make the footage look less startling. | © Comedy Central
A 2003 episode of Total Request Live treated Ben Affleck’s interaction with host Hilarie Burton as goofy MTV chaos. Burton later said Affleck grabbed her breast during the segment and recalled laughing because she otherwise might have cried. The clip acquired a much uglier second life in 2017, shortly after Affleck publicly condemned Harvey Weinstein and a viewer accused him of hypocrisy. Burton confirmed that she had not forgotten the incident, prompting Affleck to admit that he acted inappropriately and apologize. The old edit supplied laughter; Burton’s account finally supplied the missing context. | © MTV
“Be kind to one another” was more than Ellen DeGeneres’s sign-off—it became the foundation of a cheerful, highly marketable television identity. That branding collapsed into irony in 2020 when former and current employees described bullying, racist comments, intimidation and fear behind the scenes of The Ellen DeGeneres Show. Many of the most specific allegations concerned senior producers rather than DeGeneres herself, an important distinction that did not absolve the person whose name was above the door. WarnerMedia investigated, three producers departed, and DeGeneres acknowledged that her position required her to accept responsibility for the workplace. | © A Very Good Production
Pinterest has never needed a historical-content warning more urgently. Blake Lively and Ryan Reynolds married in 2012 at South Carolina’s Boone Hall, a former plantation where nine surviving cabins stand as evidence of the enslaved people who lived and worked there. Two years later, Lively’s lifestyle website, Preserve, published “The Allure of Antebellum,” a fashion editorial that romanticized pre-Civil War Southern elegance while conspicuously overlooking who paid for it. Reynolds eventually called the wedding a “giant” mistake and offered an unreserved apology—an unusually direct acknowledgment that photogenic oak trees do not erase the ground beneath them. | © Mike Coppola
One split-second costume reveal at the 2004 Super Bowl produced years of remarkably unequal consequences. Justin Timberlake pulled away part of Janet Jackson’s outfit, unexpectedly exposing her breast on live television; Jackson then absorbed most of the outrage, lost major opportunities and was removed from the following week’s Grammy broadcast. Timberlake attended that ceremony, performed and continued his ascent largely uninterrupted. His 2021 apology acknowledged that he had failed Jackson and benefited from an industry that protected white men while tolerating misogyny and racism. Seventeen years is an awfully long halftime between the damage and the apology. | © Cordon Press
The 2009 petition demanding Roman Polanski’s release reads like a roll call of Hollywood prestige, with Natalie Portman among more than 100 film-industry figures who signed it. Polanski had been arrested in Switzerland over the unresolved 1977 case in which he pleaded guilty to unlawful sex with a 13-year-old before fleeing the United States ahead of sentencing. Portman later explained that someone she respected presented the petition and she agreed without thinking carefully enough. She took responsibility and called the decision a mistake, exposing how easily professional reverence once overruled basic scrutiny in elite filmmaking circles. | © Marvel Studios
At 20, Prince Harry attended a 2005 costume party wearing a Nazi uniform complete with a swastika armband. The photograph reached newspapers shortly before commemorations marking 60 years since the liberation of Auschwitz, ensuring that “poor choice of costume” would rank among the weakest royal explanations ever issued. Harry apologized at the time, then addressed the episode more fully in 2022, calling it one of the biggest mistakes of his life and describing his shame afterward. He also recalled speaking with London’s chief rabbi and meeting a Holocaust survivor in Berlin as part of trying to educate himself. | © The Sun
Even in 2013, releasing a sexually charged song called “Do What U Want (With My Body)” with R. Kelly was a provocation carrying decades of public baggage. Gaga compounded the decision with deliberately uncomfortable performances, while the allegations surrounding her collaborator made the concept increasingly impossible to defend. In 2019, she said her thinking had been “explicitly twisted” while she was processing her own trauma, apologized for her poor judgment and promised never to work with Kelly again. She also removed their version from streaming services and later pressings of ARTPOP, giving the attempted erasure a very literal form. | © Terry Richardson
Some celebrity photographs need context; this one becomes worse as the labels are added. At a Hollywood Halloween party in 2003, a 19-year-old Khloé Kardashian dressed as a pimp and held chain leashes attached to four Black women: sisters Malika and Khadijah Haqq, and Meagan and La’Myia Good. The women were friends posing together, but that familiarity did little to neutralize the image’s racial implications when it resurfaced widely in 2022. Meagan Good had already called it a young-and-dumb mistake, which remains a more candid assessment than any publicist could comfortably manufacture. | © WireImage
Character letters are intended to show a judge the person behind a conviction. Ashton Kutcher and Mila Kunis demonstrated how badly that exercise can land when the defendant is their longtime friend Danny Masterson, who had been convicted of raping two women. Before his 2023 sentencing, both actors submitted letters praising his decency, generosity and positive influence. They later said the letters were never intended to undermine the victims’ testimony or retraumatize anyone, but intention could not undo the message. Kutcher subsequently resigned as chairman of Thorn, the anti-child-sexual-abuse organization he had co-founded, citing his error in judgment. | © Getty Images
Courtney Stodden was 16 and married to actor Doug Hutchison, who was more than three decades older, when much of celebrity culture decided the teenager was the appropriate target for ridicule. Chrissy Teigen contributed public tweets about Stodden dying or taking a “dirt nap”; Stodden also said Teigen sent private messages urging them to kill themself. When the posts resurfaced in 2021, Teigen described her former self as an insecure, attention-seeking troll and issued a public apology. Stodden accepted it but said no private apology had arrived, a notable detail in a story about cruelty performed for an audience. | © Rick Polk
No clever framing can rescue the buffet platter displayed at a 2011 Halloween party hosted by Neil Patrick Harris and David Burtka. Made to resemble Amy Winehouse’s decomposing body and presented as “The Corpse of Amy Winehouse,” it appeared only months after the 27-year-old singer died from alcohol poisoning. The image resurfaced in 2022, when Harris said it had been regrettable then and remained regrettable in hindsight. Its cruelty lands even harder because Winehouse’s addiction and deteriorating health had already been treated as public entertainment while she was alive; the platter simply extended that dehumanization beyond her death. | © Bays & Thomas Productions
Money can buy a great publicist, but it cannot make an old screenshot disappear. Deleted posts return, ancient interviews sound worse with time, and questionable Halloween costumes wait patiently for the internet to rediscover them. The famous faces attached to these moments have apologized, moved on, or simply stopped bringing them up. The internet, naturally, agreed to none of that.
