Cracked (which was a print magazine until it went online in 2007), despite usually being pretty good about avoiding this trope, would occasionally stumble into it. One of the worst examples was in 1995, when they attempted to parody some of the new video games that summer and came up with something called NBA Gam - "the slammin'est, gammin'est game of them all!" (Groan.) The joke was that it was basically NBA Jam, but with the teams' cheerleaders playing, and the "cover image" showed screaming bimbos in shorts and tank tops hurling each other through the air (the cartoonist apparently having confused basketball with wrestling). In addition to the obvious Values Dissonance of the premise ("Look at these girls elbowing and shoving each other! They think they're guys! Ha, ha!"), the pun was an obvious reference to "gams," the early 20th-century slang word for women's legs (itself derived from the French word jambes, meaning....well...."legs"); problem was, that word had been outdated for nearly two generations by the time Cracked used it (and worse, most kids who were reading probably just assumed they had misspelled the word "game," thus nearly ruining the joke). In any case, the joke became discredited the very next year, when female basketball players launched their own version of the NBA.
National Geographic Kids was a particularly egregious example, seeing as it was written for kids by people with an apparently very dim view of children's capacity for learning. Aside from the fact that the magazine was almost entirely comprised of either advertisements or advertisements masquerading as articles, the writers decided it was necessary to appeal to children using outdated (not to mention ludicrous in any time period) slang. A particularly pertinent example occurred in their "review" (read: advertisement) of Harry Potter and the Prisoner of Azkaban when discussing the costume changes from the last two films: "Harry and the gang now dress in hip street clothes instead of their stuffy Hogwarts uniforms."
In general, most attempts to depict the musical interests of a young, "hip" character end up as this. For example, if the character likes "heavy metal," they will invariably listen to music which is either not actually metal at all, or such painfully bad metal that metalhead viewers usually want it to stop even more than the rest of the viewers.
The band Leetstreet Boys seems to be purposefully invoking this trope in their songs, most notably in the song "Yuri The One For Me". The band members can't possibly be younger than mid twenties, and the lyrics include such lines as:
A Washington Post review of Katy Perry's album Teenage Dreams and its song "Last Friday Night" says: But concerned parents of young Katy Perry fans, don't fret — this woman might have more in common with you than with your kids. When it's time for Perry to reflect on her 3 a.m. follies, she stiffly sings "That was such an epic fail". It sounds like a clueless parent's attempt to speak teenager. (Be that as it may, the song was her fifth number-one hit from the album, the first time a female musician has pulled that off.)
In 1995, CompuServe released "Internet In A Box For Kids." It was basically the grown-up version "Internet In A Box," except with a videotape on proper internet usage along with an internet monitoring software program for parents to block sites they deemed inappropriate for their children. While the included video mostly averted this (probably because it featured actual children explaining how to properly use the internet), the box art was filled to the brim with Totally Radical imagery and lingo. Such as a kid screaming "Totally Internet!!!"
For Better or for Worse creator Lynn Johnston, in an effort not to sound dated ten seconds later, made up her own teenage slang phrases, which, since they were still being coined by a middle-aged woman, tended to sound pretty awkward anyway. Notable examples include "going/gone roadside" (i.e., putting out); also, "foob" (a portmanteau of "fool" and "boob"), close enough to the strip's actual acronym that snarkers now routinely call the strip Foob.
This really shone through because, well, it was a newspaper comic, which are not known for giving their readers the benefit of the doubt in intelligence... between that and just not having much space, Johnston would thus have to explain what her made-up slang meant... with slang or euphemisms that were Totally Radical.
In Zits, Jeremy had to teach his dad not to say "What's up, dood?" Unfortunately, though he could pronounce "Whatup, dude?" (relatively in use at time of publishing), he had no idea what it meant.
Parodied in one strip where Jeremy tries to get a slang word of his own invention to catch on: "Plasmic". It works about as well as you'd expect.
Calvin and Hobbes both averted and parodied this trope in a strip wherein Calvin made up his own slang, just to prove to his father that it was possible. ("Don't you think that's totally spam? It's lubricated! Well, I'm phasing.")
Radical! is a pinball machine about skating whose playfield resembles a skate park and whose artwork embodied '80s skater culture at its thickest.
Whether this counts as an aversion, an inversion, or a Deconstruction is open to debate, but World Wrestling Entertainment consciously avoids using its own insider lingo on the actual programming, even though that jargon is widely recognized and employed by the wrestlers themselves. This means practically zero use of the old "carny talk" terms such as "face" and "heel", or even newer terms such as "blade." (Occasionally a Genre Savvy performer will break Kayfabe and actually use one of the terms, but this practice is not encouraged.) On the other hand, this trope was crossbred with Bilingual Bonus on an episode of Monday Night Raw which had Alberto Del Rio introduce Jack Swagger, Dolph Ziggler, Christian, and Wade Barrett as rudos (Mexican wrestling slang for "villains").
Wrestling Society X, MTV's short lived attempt at producing a wrestling show. We're talking about musical guests playing at the start of every episode, plenty of explosions and "awesome" sound effects, not to mention the wrestling being about as flashy as possible.
WCW dipped into this when they tried to market themselves to the urban/hip hop market. They hired Master P, widely considered at the time to be Rap's equivalent of Hanson, and made an entire stable with a rap themed gimmick called the No Limit Soldiers. The worst part, though, was DJ Ran, who periodically interrupted the wrestling show to ask the fans where the rowdiest section was at.
TNA went through a period where they were intentionally inverting WWE's example above: they *constantly* threw out insider lingo, openly referred to "the script", talked about "turning" and "swerves", etc. etc. This was in the middle of their "Wrestling is still real" kick, and was a pretty blatant attempt to snag the Internet Wrestling Community that the WWE seemed to take every opportunity to piss off... Except it was so blatant and self-contradicting (how can something be "real" one break while someone gets chastised for "going off-script" the next?) that it backfired spectacularly and got the IWC to basically make fun of them even worse than they were before. Fortunately, it didn't last long and has all but vanished.
Reed: I told you, Adam, Antony and Cleopatra has nothing to do with rap! Adam: Oh yeah? Well, where does Cleopatra come from? Reed: Egypt. Adam: And what continent is Egypt on? Reed: Africa. Adam: Africa... African-Americans... rap! Boom! Hit it! There was a red-hot mama and her name was Cleo A babe born in Egypt but she moved to Italy-o She hooked up with a dude who was built like a tree Her old man's name was Mark An-an-an-an-an-an-an-an-
The published script to their stage show includes a tongue-in-cheek footnote remarking that they are only too aware that rap as a signifier of youth and coolness was hopelessly cliched even back when the "Othello Rap" was originally added in 1987, but they keep it in because it's consistently one of the most popular parts of the show with audiences.
Matt Smith (no, not that one), original presenter of Radio 4's children's show Go4It in 2001, was more than a little prone to this and extensively parodied on the radio version of Dead Ringers. His successor Barney Harwood (who would later go on to present Blue Peter) was rather more restrained.
National Cynical Network's "Chap in the Hood", with a crisply accented Briton interjecting urban slang into his monologue, joined in the finale by a Cockney rival doing the same.
An episode of the CBC comedy news show This Is That had a teacher who switched to talking in this sort of forced slang in class. It worked.
Parodied in a fake ad by The Vestibules, in which a company desperately tries to target a new customer demographic:
Teenager: (With rock music playing in the background) Yeah, Kentworth-Haynes Olde English Tea Biscuits are cool, and radical, and they're not things that old people eat! ... I like to eat 'em when I'm doing extreme sports, dude! And by the way I should know, because I'm wearing large pants that are fashionable now. Announcer: Made according to a traditional cool time-honored English recipe that combined the radical stone-milled flour with an extreme light country fresh taste, Kentworth-Haynes Olde English Tea Biscuits are guaranteed fresh - and they are cool!
Paranoia: Played for laughs with the Death Leopard secret society, who are among the few in any universe who would actually say "Totally radical, dude!" and mean every word of it. (In Zap games, talking like a dodgy take on a 1980s surfer dude is all but expected).
An unfortunate moment in Mutants & Masterminds: Hero High had Lucien Soulban jump into this, by recommending renaming a number of skills "Yo, dis da shizzle, boy!"
In Flower Drum Song, Wang San annoys his parents with his use of slang, for instance by trying to explain to his father that Helen has "got a yen for" his older brother:
Wang: A yen? San: That's when someone sends you—and Ta sends her. Wang: What language are you speaking? San: That's bop, Pop!
Originally, "The Rap" from Starlight Express was entirely plot-relevant, though it was clearly a product of The Eighties. In The Nineties, the song was rewritten to comply with the musical's newly changed plot, but sounded even more dated than before ("Nah, diesel's wicked! That diesel's sweet!"). Its final incarnation for the twenty-first century, complete with "Hip Hoppers" replacing the previous trio of boxcars, was, in fact, totally'radical', to the extent that not a single lyric remained from the first version of the song. This version must be seen to be believed. Needless to say, a CampBisexual electric engine rapping "I've got the pull! I'm takin' you to school!" is hilarious enough even without the choral assertion that racing is "the fastest, the dopest, the meanest, the quickest, the raddest, the baddest."
All four characters in [title of show] occasionally indulge in this, with terms like "hangry" (hungry + angry) and "fuxellent" (you can probably guess). Subverted in that while most of the slang terms used in the show were more or less made up, the fanbase actually embraced them after the fact.