17 Outdated Ads That Tried (And Failed) To Understand Teen Culture
As I wandered through the wild world of vintage advertising, I stumbled upon a true goldmine: a collection of ad campaigns that tried—and failed spectacularly—to connect with teens.
These 17 cringey masterpieces are like time capsules of awkwardness, each one more delightfully off-target than the last. From painfully out-of-touch slogans to bizarre attempts at being “hip,” these ads are relics from an era when marketers were clearly guessing—and guessing wrong—about what made teens tick.
But that’s what makes them so entertaining! I couldn’t help but chuckle as I unearthed these gems, and I’m betting you’ll laugh right along with me. Whether you’re here for the nostalgia, the irony, or just to cringe in solidarity, buckle up—this hilarious journey through advertising misfires is one you won’t want to miss!
1. Levi’s ‘Hipster Jive’ Campaign
Once, I came across a Levi’s ad that tried too hard to speak the “hipster jive.”
Picture this: a 1970s teen, decked out in bell-bottoms, bopping awkwardly to a disco beat. The ad promised to make you the coolest cat on the block.
Unfortunately, the attempt to blend hip jargon with denim fashion fell flat, leaving teens more puzzled than impressed. It’s a classic example of trying to surf the wave without a board. Did I mention the tagline? “Groove Into Cool”—more like, “Stumble Into Awkwardness.”
2. Pepsi’s ‘New Generation’
Pepsi once dubbed itself the drink of the “New Generation,” hoping to capture the hearts of cool kids everywhere.
I recall seeing this ad in a magazine, where a teen, amidst a sea of boomboxes, seemed more overwhelmed than refreshed.
The neon lights were blinding, and the message was clear: this was an ad trying way too hard. Pepsi aimed to be the soda for trendsetters but ended up being more of a fizzled attempt. Kudos for the effort, though!
3. McDonald’s ‘Yo! I’m Lovin’ It’
Remember when McDonald’s tried to go street with their “Yo! I’m Lovin’ It” campaign?
Picture a 1990s teen, oversized clothes and all, munching on a burger amidst graffiti. It was like watching your uncle try to rap at a family gathering.
While McDonald’s wanted to resonate with urban youth, it felt more like a cringey dance move at a wedding. Despite the catchy jingle, teens were left wondering who exactly was loving it. Spoiler: not them.
4. Sprite’s ‘Obey Your Thirst’
Sprite’s “Obey Your Thirst” campaign urged teens to break free and be themselves.
I remember seeing a teen in a bucket hat, sunglasses on, clutching a Sprite like it was the Holy Grail. Skateboards surrounded him, as if drinking Sprite was a rebellious act.
While the message was about authenticity, the execution felt a bit too scripted. Teens saw through the facade, realizing that true rebellion wasn’t found in a can. Still, it was a cool attempt at being “not so cool.”
5. Reebok’s ‘Pump Up and Air Out’
Reebok’s “Pump Up and Air Out” campaign was all about inflating your sneaker game.
Picture a 1990s teen, awkwardly crouched, pumping air into their sneakers like they were about to take flight.
The basketball courts were the backdrop to this peculiar ritual. While it promised an edge in sports, it mostly aired out confusion. Teens were left wondering if they needed a user manual to figure out these kicks. It was a fun concept, but maybe just a little too hot-air-filled!
6. Gap’s ‘Khaki Swing’
Gap’s attempt to make khakis hip was, well, a swing and a miss.
Their “Khaki Swing” ad featured a teen doing his best impression of a jazz dancer. Surrounded by trumpets and trombones, he looked more like he was having a wardrobe malfunction than a dance party.
Despite the jazz vibe, teens weren’t exactly lining up to trade their jeans for khakis. This one left us questioning if khakis could ever be cool. Spoiler alert: they never really caught on.
7. Burger King’s ‘Subservient Chicken’
In the mid-2000s, Burger King introduced the “Subservient Chicken,” hoping to capture the teen market with interactive fun.
I remember thinking, “What am I even watching?” as a person in a chicken costume took orders from users online.
It was a bizarre blend of virtual play and fast food, leaving teens scratching their heads rather than craving burgers. This ad was maybe more surreal theater than appetizing suggestion. Still, it provided a quirky moment in advertising history.
8. Old Spice’s ‘Smell Like a Man, Man’
Old Spice’s “Smell Like a Man, Man” campaign aimed to redefine masculinity, but for teens, it was more of a head-scratcher.
Picture a teen, staring at the body wash, amidst an absurd tableau of rugged masculinity—think bearskin rugs and muscular statues.
The ad’s humor was intentional, yet the attempt to connect with young men seemed over-the-top. While it was memorable, it left us wondering if smelling like a man was really worth the theatrics.
9. Coca-Cola’s ‘Mean Joe Greene’
Coca-Cola tried to melt hearts with their “Mean Joe Greene” ad, featuring a heartwarming moment between a football player and a generous teen.
But honestly, the sentiment felt more like a punt than a touchdown with actual teens.
The gesture of sharing a Coke was sweet, but for the youth, it was less of an emotional connection and more of a commercial cliché. Still, it remains a classic, albeit a slightly saccharine one!
10. Hubba Bubba’s ‘Big Bubbles, No Troubles’
Hubba Bubba’s promise of “Big Bubbles, No Troubles” was its way of tapping into the carefree teen spirit.
I can vividly recall a teen, cheeks puffed, attempting to blow the biggest bubble, surrounded by the glow of arcade games.
The simplicity of gum couldn’t mask the underlying attempt to create a bubble-blowing subculture. While fun, it didn’t quite stick as intended. Teens kept chewing, but mostly for the flavor, not the philosophy.
11. Nintendo’s ‘Now You’re Playing with Power’
Nintendo’s “Now You’re Playing with Power” slogan intended to elevate gaming to epic levels.
Imagine a 1980s teen, controller in hand, eyes wide with imagined possibilities, surrounded by pixelated heroes.
The ad aimed for empowerment, but the over-the-top dramatics sometimes felt like fantasy overload. While it connected with gamers, non-gamers viewed it as a glimpse into an alternate universe. It was a bold attempt that carved its niche, albeit in a niche world.
12. Puma’s ‘For The Streets’
Puma’s “For The Streets” ad tried to root itself in urban culture, aiming to make teens feel like streetwear legends.
I remember seeing a teen, snug in Puma sneakers, standing at a gritty street corner with confidence. However, the forced “street cred” vibe felt more like a set piece than a genuine backdrop.
While the shoes were stylish, the ad’s attempt to connect with city-savvy youth was a bit too on-the-nose. The streets didn’t exactly echo with praise.
13. Mountain Dew’s ‘Do the Dew’
Mountain Dew’s “Do the Dew” campaign was a call to action, inspiring teens to embrace extreme sports.
Picture a teen on a BMX, mid-air, drink in hand, surrounded by the chaos of ramps and graffiti. While meant to ignite a rush, it occasionally veered into over-hyped territory.
Despite this, it found footing with adrenaline junkies, even if the rest of us were left dizzy. It captured a niche spirit, though sometimes at the expense of clarity.
14. Dr Pepper’s ‘Be a Pepper’
Dr Pepper’s “Be a Pepper” campaign was all about joining the fun, encouraging teens to embrace individuality.
Picture a 1970s teen, can in hand, amidst a swirl of disco lights and musical notes. While the ad’s jingle was catchy, the push to “be a Pepper” felt as if it tried a bit too hard to create a movement.
Teens were left humming the tune, but not entirely convinced of its message. It was a quirky, albeit slightly off-key, effort.
15. Nike’s ‘Just Do It’
Nike’s “Just Do It” remains iconic, but for some, its all-encompassing motivation became a bit, well, overdone.
Imagine a determined teen on a track, surrounded by motivational quotes, pushing limits that seemed slightly out of reach.
While it inspired many, the over-saturation of the message sometimes felt like an endless loop of pep talks. Teens either embraced the slogan or found themselves ironically quoting it while avoiding gym class. A memorable mantra, but occasionally exhausting.
16. Taco Bell’s ‘Think Outside the Bun’
Taco Bell’s “Think Outside the Bun” was a cheeky nudge for teens to embrace tacos over traditional burgers.
Picture a rebellious teen, taco in hand, amidst a forest of fast food signs. The ad pushed innovation, but sometimes felt more like a rebellious act against burgers than genuine culinary choice.
While tacos did have their fans, the messaging occasionally seemed more provocative than persuasive. It was a tasty attempt, yet perhaps a tad too spicy for some.
17. Calvin Klein’s ‘Nothing Comes Between Me and My Calvins’
Calvin Klein’s bold “Nothing Comes Between Me and My Calvins” campaign sought to intertwine fashion with identity.
Picture a laid-back teen, striking a pose in denim, surrounded by a haze of high fashion. While the ad was provocative, for some, it ventured into the world of high drama.
Teens were either drawn to the allure or left pondering the depth behind the denim. It was a daring attempt, undeniably memorable, yet perhaps a touch melodramatic.