Halloween thrives on its underworld connotations, a festivity where the macabre and the whimsical collide. So, when celebrities dive into this spooky pool, it should be to swim in style, and preferably not to drown in dreadful design. Yet, some of these superstars' costumes end up being slightly, egregiously, off-mark, and the audiences on duty wind up wishing they could dig those nightmares out of their minds and into digital-graves. 

In Hollywood, every outfit has the potential to become an internet legend: for better or worse.

Like any little step a Tinseltown resident takes, Halloween costumes that celebrities don spread fast on social media; they are either instant classics or instant public embarrassments. Costumes that hit all the right notes: clever, relevant, and visually striking, become internet gold. However, if an outfit falters due to poor execution, questionable taste, misguided political and regional undertones, or a complete lack of inspiration, the broadcaster of said misstep becomes a meme magnet.

Virality, therefore, is less about sparkle and more about spectacle, regardless of whether it is admired or mocked.

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When you dress like Gotham’s Dark Knight but come out looking like a confused summer termite, prepare for the social media swarm. 

In 2020, the Billboard hit rapper Travis Scott donned a Batman costume that was less brooding vigilante and more perceived as a confused termite mound. His choice of a brown leather ensemble, complete with a just-as-brown flowing cape and brown half-faced mask, was met with a tidal wave of online travesty. Social media compared the look to everything from cockroaches to cartoon villains gone wrong.

The fallout was so severe that the Eminem-humbling, sonic supreme Scott deleted his Instagram, transforming the costume into a textbook lesson on how even the boldest celebrity Halloween plans can backfire spectacularly.

Travis Scott was far from alone in the quest for memorable Halloween costumes that spectacularly missed the mark. The day of the macabre has seen many celebrities make just as big, or even bigger, splashes for all the wrong reasons. From botched homages to baffling fashion choices, these costume catastrophes have become just as legendary as Scott’s infamous brown Batman suit.  

Heidi Klum tried to bring Jessica Rabbit to life using pounds of silicone and latex, but ended up strikingly close to a plastic surgery horror show. The curvaceous cartoon character morphed into something more reminiscent of a wax museum exhibit gone wrong. Onlookers struggled to reconcile the hyper-real with the hyper-creepy.

Even the queen of Halloween could not save this costume from sliding straight into uncanny valley territory. The effort was considerable, but the effect was counterproductive. Klum’s usual flawless metamorphoses gave way to awkward exaggeration, proving that sometimes 3D should stay off the agenda when translating 2D characters.

Anne Hathaway’s Halloween look for 2024 was a haunting blend of Statue of Liberty and "a zombie version of Chappell Roan, dressed as the Statue of Liberty to perform at the Governors Ball", according to Cosmopolitan. Sporting a platinum blonde bob, pale makeup with dark eye accents, dark purple lips, and a Statue of Liberty crown atop her head, she paired this with a black leather jacket and a playful 'Boo York City' shirt. 

Some even noted a slight Harley Quinn flair to the styling. While the costume could be everything experimental, one could ponder for a while, trying to decide exactly what Hathaway meant to convey as inspiration for the pop-sacred festivities. The thrown-together costume is, on top of it all or Gotham City, a far cry from the high note-hitting Hathaway's iconic, sleek Catwoman costume in The Dark Knight Rises, as well.

Joan Rivers conjured a parody of Miley Cyrus’s notorious MTV VMA outfit, pushing the envelope into grotesque territory. With a ludicrously long fake tongue and devilish hair buns, this Halloween tribute resembled an unexpected exorcism more than a pop culture homage. While Rivers was known for her biting humor, this costume crossed from campy to creepy. Rather than channeling the moment-muddled singer's playful provocateur, Rivers embraced a caricature so outlandish it veered into nightmare fuel. It had easily been the audience's choice of one of the more unsettling celebrity Halloween moments in history.

Jessica Simpson’s tribute to outlaw country legend Willie Nelson was a masterclass in half-hearted homage. While she checked the superficial boxes for bandana, braids, and boots, her pairing of low-rise jean shorts instead of rugged denim sent mixed signals. The look blared country party more than country outlaw. This costume was a try-hard for the onlookers, seeming at once authentic yet casual enough to evoke a weekend barbecue rather than an outlaw birthday bash.

Simpson’s flirtation with authenticity was diluted by the shorts, leaving the audience bemused about whether they were at a Nashville concert or a pool party.

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The king of English charm took a walk on the wild side, or rather, a sluggish stroll. Hugh Grant’s lion costume gave roaring majesty a run for its money, one fine Halloween. 

Hugh Grant’s lion costume was so devoid of effort, it seems to have inspired pity rather than pestilence. His woefully wrinkled onesie, limp mane, and a pair of sneakers that probably had not seen sunshine for years transformed the king of the jungle into the house cat who quit mid-nap. The audience was left wondering if Grant’s costume was a stroke of existential ennui or a rushed nod to Halloween tradition.

For celebrities, Halloween is a high-wire act where the stakes are creativity and public perception. Some costumes demonstrate that even top stars can trip, sending their fashion sense plunging into the Halloween abyss. Whether a costume incites laughter or horror, it leaves a lasting impression—a haunting reminder that in the dance of fame and fright, sometimes the costumes bite back harder than the audience.

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Do you recall any Halloween costumes that made you look twice mid-jumpscare for the wrong reasons? Let us know in the comments below.