The Nineties, in particular, were infamous for using this trope with children's advertising. Around the start of the decade (perhaps in response to Bartmania), television advertisers were moving away from the cutesy/sentimental advertisements that dominated children's television for so long and, instead, began using Totally Radical lingo and "EXTREME!!!!!" kids. Many of the following examples perfectly exemplify this.
There's this commercial for the Hardee's Little Thickburger. Presumably it was pulled fairly quickly.
An advertisement for the "Slim and Lite" revision of the PSP suggests that players can "put it where they like", which typically means "shove it up their ass". Sony seems to be getting annoyed at their customers.
Sony's been particularly bad about this with their PSP advertising. At one point, an incredibly poorly-disguised viral marketing campaign attempting to masquerade as a fan website noted of the PSP, "I'd hit that." Does it even have the right ports for that?
Despite trying to win over — presumably — the kid demographic, consider how anachronistic the Chuck E. Cheese mascot is with his depiction as a "Sk8r" boy, over a decade after that fad has run its course with young kids. The mascot originally started as a suspendered, straw-hatted barbershop-type performer, appeared in the 1980s as a skateboarding mouse, went out of style, then swerved right back into relevancy when the Sk8r boy image appeared, and is now fading back out of style — all without any changes ever being made to the character itself. By time skateboarding bert-slided itself back into relevancy again, it was in the form of edgy street skating, and an edgy street skating Chuck. E. Cheese probably wouldn't go over too well with the parents of most kids.
Their current ad campaign has a child badly rapping over the beat to The Cupid Shuffle (which is only ever heard now at weddings alongside The Macarena and The Electric Slide), and then exclaiming that a thousand tickets is "like, a gazillion!"
Amp'd Mobile briefly retained a commercial gimmick which involved elderly people talking like teenagers. (One features an old black woman who uses street vernacular and says stuff like "Where you at?"; in another, an old white lady makes frequent usage of "like", "whatever" and "totally"; apparently, this commercial presumes that old Generation Gap stereotypes will die out, but racial ones never will.) Later referenced on the The Simpsons:
Marge: Yeah, I'll bet there'll be old people talking like young people, like those cell phone commercials everybody hates.
Also parodied in The Simpsons episode "Pranksta Rap", when Bart uses slang words that Lisa (and even Marge) knows aren't used anymore.
Bart: Man are you illin'.
Lisa: Rappers stopped saying "illin'" twelve years ago.
Bart: I'm keeping it real!
Lisa: They stopped saying "keeping it real" three years ago.
Bart: Mooom! Lisa's dissin' me!
Marge: "Dissin'"? Do rappers still say that?
Not that Marge can't be guilty of it herself. One episode has her trying to get Maggie to eat her baby food with the help of a sock puppet in Cool Shades who says "Yo-Yo-Yo!" constantly. Marge is also aware of this trope and struggles to avoid it sometimes. She once used the word "cool" with Lisa and anxiously inquired as to whether kids still say it. Lisa confirmed that they do.
What happens when a cell-phone advertisement becomes a big hit, but ad execs don't fully get the joke? Apparently, teenage girls talking to one another in textspeak... face-to-face.
Parodied in a series of Volkswagen commercials which would end with a grey-haired, thickly accented Peter Stormare "un-pimping" someone's ride...which is a fancy way of saying "trashing it in spectacularly hilarious fashion (and replacing it with a sober, sensible VW)."
German Guy: Yo, Mike, you vant us to un-pimp zis ting, let me hear you say 'vhat'?
Car is launched from trebuchet
The Cliff's Notes banner ads, some of which were, at the time of writing, visible on this very site. Among their misinterpretations of textspeak are spelling "who" as "hoo", a Zero Wing reference, and the mystifying term "xcore" (which is possibly "score" spelled with Xtreme Kool Letterz). Xcore sometimes means "hardcore."
Gas stations advertising "We got the hooch" after the popular '90s song.
EA's initial teaser for Skate 2 announced "We're dropping the deuce." While this can be read as "releasing #2", its slang meaning is "taking a shit". This was probably intentional * Doing a number 2 means taking a dump, which makes one wonder how they felt about the product.
Parodied in an Aim Trimark ad, where some executives, upon being told that their new shoe design is "sick", take most of the commercial to puzzle over whether or not that's a compliment. Then the Aim Trimark guy comes and says that he's not going to invest your money in a company run by these idiots.
Repeated by an online ad for a US government health campaign here◊
In 1968, Columbia Records ran a notorious ad in Rolling Stone showing a bunch of picket sign-toting young radicals in a jail cell with the caption "But The Man can't bust our music." For extra hilarity, the albums shown in the ad are all Classical Music. (Wendy Carlos' early electronica Switched-On Bach was a bit more far out then.)
In a commercial for Lunchables' newest product, "Wrapz", three kids lousily rap about the wrap. Possibly intentional, but still full of fail, and with slang like "A'ight" pronounced "Ah-Ite.".
An Australian example for a rather mediocre car combines this with Buffy Speak, explaining that the Holden Astra "has extra features to an exclamation mark". Um...what?
A poster advertising the Slush Puppies sold there. The right side of the poster is a generic image of some Slush Puppie cups, but the left side is in a league of its own. It consists of three open cell phones with text messages on them. They read, in order, "LuVN DA CHiLLLLLLLLLLLL TASTe and FLAVZZZzzzzzzz" "REal FRUIT JUICE ITS GOT VITA C!!!!!!!!" and "GOTTA GET A SLUSH PUPPIE PLUS!!!!!!!!!!!!!!!!!!"
Though it might bear mentioning that this one isn't quite as far off the mark as some others (at least in regards to the excessive consonants). No word on whether this speaks worse of the advertisers or "txt literacy" though.
The similar Icee cold drink at some point replaced its old bear logo◊ with a snowboarding one◊, and its current slogan (at least at Burger King franchises that sell it as of 2013) is "CHILL OUT WITH UR FAV FLAV."
Similarly, Big Daddy Pizza posters saying Narmful things like "Every other slice is a sliver", "Wanna Piece of Me?", and "Show Your Hunger Who's Boss".
An ad for Progressive seems to be an inversion. Flo, the company's mascot and resident Genki Girl tries helping out an elderly customer who uses outdated slang from the mid 20th Century. Needless to say, she has no idea what he's talking about.
There is a German PSA about hepatitis that features a hip-hoppin' syringe (filled with a hepatitis vaccine), singing about using it to protect yourself. Yes, it's as bad as it sounds.
Monster energy drinks. JUST LOOK AT THE CAN'S DESCRIPTION.
Special mention must be made of K-Mart's Back to School 2009 ads; not one but two horrendous pseudo-slang words that no decent human being will ever utter without monetary compensation: "Blingitude" and "Rockstare".
One Disney Channel ad encouraged people to stay for the upcoming shows, because after whatever was coming next, "Then it's off the heezy with The Proud Family."
A promo for a Saturday night rerun block stated that the only thing better than shaking it up on live TV is "sharing it with your biffle". Your guess is as good as ours (it may be a failed attempt to phonetically pronounce "BFFL").
Wendy's jumped on the bandwagon with their ad telling customers to "Do a spicy chicken sandwich."
A TV ad for the Game Genie in the late '80s featured a pair of Bill-and-Ted-soundalikes and opened with the phrase "Yo video game dudes, talk to me!"
The description for this Atariad explains everything.
An ad for an electronic diary for girls has one girl saying "And you can plug in your MP3 for major tuneage!
In Italy they started adding in the buses ads reminding people to leave your seat to elder people. One of them just says "Be polite-leave your seat", while the other one says "leaving your seat is TOO MUCH AWESOME!"
The phrase "Mickey D's" as a nickname for McDonald's.
A UK Pizza Hut billboard gives customers the instruction "Max Your Chat", leaving most people over the age of 0 utterly baffled.
As if Ovaltine's advertising were not bad enough, there were a series of ads featuring Radio Ovaltine, which was basically run entirely by kids using "radical" lingo and playing nothing but the Ovaltine jingle sung by different kids, each one in a different style. Each performance was followed with the kid DJ saying something along the lines of "Totally radical!"
Old Israeli toy and game advertisements frequently used the word madlik (מַדְלִיק), a ‘90s word for ‘cool’, entirely obsolete in modern Hebrew.
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The ads for the new Hot Pastrami melt from Subway claim it has power chords of tasteocity. If you were to say "Power chords of tasteocity" in conversation, people would probably assume you're having a stroke.
For more Subway slang fail, there's one ad, in their long-running "fast-food will make you a fat slob" campaign, in which a burger combo is stated as giving someone a "badonkadonk butt". Three things: 1. Fast food wouldn't give you a badonkadonk butt, as it connotes a big, shapely butt, not a flabby one; 2. Badonkadonk is usually used positively; 3. The phrase "badonkadonk butt" is redundant.
There was a hilarious(ly awful) Duncan Yo-Yo commercial made in 1994 that showed two different kids: One was a stereotypical Hollywood Nerd sitting on a chair in his living room playing a Sega Genesis (with Atari 2600 sound effects, of course) and a stereotypical cool kid with a backwards baseball cap "enthusiastically" playing with a Duncan Yo-Yo. The commercial ends with the kid saying, "You want speed, action and excitement? Get a Yo-Yo!" ... Really?
This ad for the boardgame Crossfire is an interesting variation. How do corporate advertising geniuses imagine a future that would appeal to the target audience (pre-teens and teens) while also promoting their new product? Why, of course by showing kids in leatherjackets playing the game like a Rollerball/Thunderdome-style deathmatch of gladitorial combat (The loser spins into oblivion), surounded by their cheering fans, while a cool hard rock song is playing in the background. The Angry Video Game Nerd even made a video about it (as his alternate persona Board James)
McDonald's' McWorld kid-targeted campaign from the early to mid 90's, which had the theme of "a world run by kids". The commercials depicted very stereotypical kid-instigated changes, with the big one being McDonald's food and restaurants becoming the centerpiece of the world. Mind you: This is a good decade before Super Size Me premiered.
The Hi-C commercials from the mid-1990's that contrasted kids and adults (right down to an adult's idea of a Hi-C commercial vs. a kid's idea).
The commercials for Kellogg's Frosted Mini Wheats that ran in the early-mid 1990's, such as this one, which showed conflict between the kids' love of the frosting (with bad "heavy metal" music in the background) and the adults' love of the whole wheat (with boring "adult music" playing in the background). Noticing a chronological pattern here?
Nickelodeon's infamous "Don't Forget About Breakfast Time" animated rap video. Along with their "democracy" video.
To some, advertisements for Young Adult novels can fall into this, especially those done by Fierce Reads. Take, for example, this oppressively narmy ad, complete with the most banal attracting phrases and a stereotypically pop song about the joys of reading. There's not much else that could make a 16-year old not want to read.
A '90's Pepsi commercial tried to convey that Pepsi drinkers are cooler than Coke drinkers by giving Coke to a group of teenagers and Pepsi to a group of senior citizens. The result was that the teenagers took to sitting around playing chess, while the seniors began skateboarding and dancing. The last scene showed an elderly man taking a swig of Pepsi and proclaiming, "This stuff is really radical!"
The Burger King Kid's Club commercials of the mid-90's (again: noticing a common time frame here?) were particularly egregious examples. Their spokesperson was a cool kid with all the necessary "makings" of one (shades, a backwards baseball cap, etc.). The commercials themselves often depicted kids doing everything from playing in rock bands to being disgusted by their relatives just for showing them affection.
Honey Nut Cheerios, during (when else?) the early/mid-90's, attempted to market their cereal to a younger demographic by ditching the warm and friendly tone of their 80's commercials for a more hip and edgy style: they retooled Buzz Bee into an arrogant Jerk Ass who talked like Roger Klotz and challenged people (including Sonic The Hedgehog) to races, with a bowl of Honey Nut Cheerios as the prize. The retool didn't sit well with audiences, and by about 1995, Buzz Bee was given a much nicer personality akin to the 80's.
A particularly egregious example was a commercial for Twix that aired in early-1997. Its jingle went like this: "Some people like... peace and quiet" ::cue four shushes:: "... and some people like things to be LOUD! LOUD! LOUD! LOUD!" ::cue some stereotypical mid-90's grunge/alternative music:: The shortened version of this commercial was even weirder, with the lyrics going: "There once was a boy... who wanted everything... to be LOUD! LOUD! LOUD! LOUD!"