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10 Biggest Celebrity Snapchat FAILS

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Snapchat’s disappearing photos had a funny way of sticking around forever.

By the fall of 2016, Snapchat had become the default channel for celebrities who wanted to skip the publicist and post directly to fans — ten-second clips, no filter on the truth, and none of the delay of a traditional photo shoot. That immediacy is exactly what made the platform a minefield. TheThings Celebrity’s countdown, “10 Funny Celebrity Snapchat Posts,” rounds up the decade’s defining examples of stars getting caught mid-overshare, plus a few messes Snapchat made entirely on its own.

• Kylie Jenner, one of the platform’s most-followed users under the handle “kylizzlemynizzl,” drew accusations of blackface and cultural appropriation after posting heavily tanned, stylized photoshoot images across her accounts.
• Usher inadvertently oversharing on his own Snapchat Story with a sauna selfie he tried to cover with a single emoji — a sticker that didn’t come close to doing its job.
• Snapchat itself landed in the countdown for its 2016 face filters, including a Bob Marley lens slammed as digital blackface and an anime-style filter widely criticized as yellowface.

Kylie Jenner’s Handle and the Photoshoot Backlash

Jenner’s Snapchat presence in 2016 was less a side project than a media operation — “kylizzlemynizzl” pulled in millions of views on stories that ranged from makeup tutorials to behind-the-scenes glimpses of her lip kit empire. The trouble came when photoshoot images she shared, both on Snapchat and across her other accounts, showed her skin darkened and her features styled in a way critics immediately flagged as blackface. The backlash spread fast, with commenters accusing her of profiting off a look she wouldn’t otherwise be criticized for wearing, and the images became one of the most-cited Snapchat controversies of the year.

Usher’s Sauna Selfie Emoji Malfunction

Usher’s entry is the platform’s oldest problem in its purest form: Snapchat encourages spontaneity, and spontaneity doesn’t always account for camera angles. The singer posted a shirtless sauna selfie to his Story and attempted to preserve some modesty with a single emoji placed over the frame — except the sticker wasn’t nearly large enough to cover what it needed to. Screenshots circulated within minutes, because on Snapchat nothing is ever really as temporary as the app promises.

One emoji, one very exposed sauna selfie — Usher learned in real time that a ten-second Snap can outlive a ten-second decision.

Platform Operations Become Central Narrative

Not every fail in the countdown belonged to a celebrity. Snapchat’s own engineers drew heat in 2016 for a run of face filters that critics said crossed a line rather than just adding a laugh. The Bob Marley lens, rolled out around 4/20, digitally darkened users’ skin and added dreadlocks and a knit cap — instantly labeled digital blackface by users and writers alike. A separate anime-inspired lens, which slanted and reshaped users’ eyes, drew the same criticism in reverse, blasted as yellowface. Both filters were pulled amid the backlash, but not before thousands of users had already posted with them.

The countdown treats these platform-level fails with the same weight as the celebrity ones, and for good reason — Snapchat’s filters reached far more people in a single afternoon than any one star’s Story. Detailed records on the roundup’s lower-ranked entries are thinner, but the throughline across all ten spots is consistent: a feature built for goofing off in private kept exposing things — bodies, opinions, bad judgment — that were never meant for a wide audience.

Snapchat’s culture of instant, unedited posting would keep producing these moments long after this particular countdown wrapped, the same way it keeps tripping up anyone who forgets the front-facing camera doesn’t come with an undo button — something actors who’ve ruined their careers on social media and even reporters caught out on the same platforms could tell you firsthand.