Try Hard, Fail Harder: Why Brands Keep Fumbling TikTok and the Rare Geniuses Who Actually Figured It Out

There is a specific flavor of cringe that only TikTok can produce. You know the one. A brand account posts a video that uses a trend from four months ago, captions it with slang that was already ironic when it was current, and ends with a call to action that has the energy of a substitute teacher trying to get the class to settle down. The comments are a crime scene. The ratio is catastrophic. Somewhere, a social media manager is updating their LinkedIn.

This happens constantly. Constantly. And yet brands keep doing it, celebrities keep attempting it, and the cycle of cringe continues uninterrupted. Why? What is driving otherwise intelligent marketing teams to keep charging into the TikTok content machine like it owes them something?

We went looking for answers. We also went looking for the exceptions — the brands and celebrities who managed to do TikTok in a way that didn't make anyone feel like they needed a shower. Those people exist. There are fewer of them than you'd hope, but they're out there, and they have lessons to teach.

The Anatomy of a TikTok Fumble

Let's start by being specific about what we mean when we say brands are fumbling TikTok, because "bad social media" is a broad category and the TikTok variety has its own particular characteristics.

The most common fumble is the trend lag. A sound or format blows up on TikTok, reaches peak saturation, starts getting used ironically, dies, and then — two to six weeks later — a brand account posts their version of it. By this point, the original trend has been memed into the ground and resurrected as a different meme entirely. The brand's version lands like a time traveler who showed up to a party the day after it ended.

The second most common fumble is the authenticity overclaim. This is when a brand or celebrity's team crafts a video that is very carefully designed to look spontaneous and ends up looking like the most labored thing ever produced. "We're just like you!" energy, executed with a production budget and three rounds of approval from the legal department. Gen Z, who has been marketed to since birth and has developed a finely tuned detector for inauthenticity, clocks this immediately.

The third fumble — and arguably the most embarrassing — is the slang misfire. Using Gen Z vernacular incorrectly, or using it correctly but in a context that makes it clear the writer learned it from a glossary rather than from actual usage, is the social media equivalent of a dad saying "that's so fetch" in 2024. It signals effort in a way that undermines the entire attempt.

The Celebrity Version Is Its Own Disaster Category

Brands fumbling TikTok is one thing. When aging or out-of-touch celebrities do it, the stakes are somehow higher and the crashes are somehow worse.

The celebrity TikTok fail tends to follow a specific pattern. Someone in their team convinces them that they need to "connect with younger audiences." They film a video that is technically a TikTok format but that has the energy of someone who has watched exactly one TikTok and decided they understood it. They post it, it goes viral — but not in the way they wanted. The comments are not kind. Suddenly there's a whole discourse about whether the celebrity is "out of touch" that probably wouldn't have existed at all if they'd just not posted.

The irony is that the attempt to seem relatable often makes celebrities seem less relatable than if they'd just... been themselves. Nobody expected a 55-year-old actor to be on TikTok doing the latest dance trend. But when they try it and fail, it becomes a whole thing. The absence of a TikTok presence is invisible. A bad TikTok presence is very, very visible.

The Cringe Hall of Fame (No Names, Just Vibes)

Without getting too specific — because honestly the examples change weekly and anything we name will be replaced by something worse by the time you read this — here are the archetypes of TikTok cringe that appeared with alarming regularity in 2024:

The Corporate "We're Fun" Video: Features employees dancing in a break room to a sound that was charming six months ago. The dancing is technically correct. The energy is legally dead.

The Celebrity "Relatable" Moment: A famous person films themselves eating cereal or doing laundry or some other mundane task to prove they're just like us. The cereal is organic and the laundry room is the size of a small apartment.

The Brand Jumping on a Tragedy-Adjacent Trend: Someone in the content calendar meeting did not think this through. The comments are brutal. The apology comes three hours later.

The Forced Collab: Two celebrities or a celebrity and a brand do a TikTok together that has the chemistry of a business meeting and the spontaneity of a tax return.

The Rare Wins and What They Have in Common

Here's where it gets interesting, because some people are genuinely getting it right, and the pattern of their success is pretty consistent.

The brands that work on TikTok have mostly figured out that the platform rewards genuine weirdness over polished performance. Duolingo's unhinged green owl mascot energy. Ryanair's aggressively self-deprecating content. These work not because they're on-trend but because they have a consistent, distinctive voice that feels like an actual personality rather than a content strategy document.

The celebrities who crack TikTok tend to be the ones who are using it to show something real — a genuine hobby, an actual sense of humor, a behind-the-scenes moment that wasn't staged. The content doesn't have to be high quality. It has to feel honest.

The common thread: stop trying to go viral and start trying to be interesting. Viral is a byproduct. You can't manufacture it by reverse-engineering trends. You can manufacture it by being consistently, authentically yourself in a way that happens to connect with people.

What Gen Z Actually Respects

We're going to be direct here, because the discourse around "what Gen Z wants" is often condescending and wrong. Gen Z is not a monolith. They do not have a unified set of values that brands can unlock with the right hashtag.

What they tend to respond to — based on what actually performs, what gets shared without irony, and what generates positive engagement rather than ratio engagement — is pretty simple: competence, self-awareness, and not wasting their time.

Competence means doing the thing well, whatever the thing is. Self-awareness means knowing what you are and not pretending to be something else. Not wasting their time means having a reason to exist beyond "we need to post today."

The brands and celebrities who hit all three of those marks? They don't need to chase trends. The content finds its audience because it's actually worth watching.

Everyone else is going to keep showing up to the party the day after it ends, and the comments will continue to be a crime scene. We'll be here watching. It's the most reliable entertainment on the internet.