A throwaway gag in one episode involves Dr. Drakken learning the phrase "off the heazy" from a book on teenage slang, prompting Genre Savvy Shego to question its validity. And apparently, he loved being "hip" so much that he continued to use terribly out-dated or poorly delivered phrases for the rest of the series. Thanks to Drakken's VA, John DiMaggio, it was hilarious. "Why you got to leave me hangin' like that, yo?" and "Word to yo' mutha!" are examples.
Also briefly attempted by Mrs. Dr. Possible. Kim's reaction: "Mom, you're already cool. Don't push it."
Teenage Mutant Ninja Turtles (1987) used (largely out-of-date) California surfer/valley-speak. It was primarily Michaelangelo who spoke like this. Except for the beginning and ending of the first live action movie, the other Turtles only did it sufficiently rarely that it was usually considered out of character when they did.
The Turtles' early overuse of Totally Radical speech was parodied in a sketch on Robot Chicken, where the Turtles said "Tubular!" "Radical!" "Awesome!" "Reaganomics!"
Heck, the Turtles parodied themselves in the live action movies. Donatello could never pick out the right word. "A Capella!... Perestroika? Oh, I know! Frere Jacques!"
In Turtles Forever, one of the 80s Turtles exclaim "Totally Radical!" when riding in the 2K3 Turtle Van.
In the 2003 TMNT series, they don't talk like this, save Mikey, who tries it, but the others tell him to cut it out. (Naturally, he loved the 1987 Turtles.)
Oddly also lampshaded (sort of) in once episode where the cast laments the "Kooks" (non-local) and such stealing their "lingo" and using it without the proper pronunciation or usage.... Silly Nickelodeon.
Parodied extensively in an episode with the product X-Stream Blu (which notably contains a hip spelling) in the spirit of Go-Gurt and like commercials. Among the blatant attempts to seem hip include the phrases "to the max", "legit-ass contract", and the random string "Sick! Tight! Cyber! Awesome!" Yeah, that energy drink is cyber.
One of the executives in the background during the Totally Radical moments tends to shout out how this type of pandering has destroyed his dignity. "My son won't even look me in the eye anymore!"
In one of the first episodes, Principal Scudworth goes undercover to a party and constantly spouts phrases like "raise the roof" and "tight", among others.
In the direct-to-DVD movie Bratz: Rock Angelz, the main characters can't seem to go two minutes without exclaiming that something is totally "slamming", "rocking", "styling", "scorching", or, in the case of a punk rock night club, "punkalicious".
Jazz is supposed to be the young, cool, hip robot. Unfortunately, he's usually about 30 years behind with his "cool" phrases, and nobody seems to notice.
This is somewhat justified in the 2007 movie, where it is mentioned that the Autobots learned all their human cultural information from the internet. We're lucky he wasn't talking in LOLcat.
And Transformers Animated brings us the Headmaster, who uses gamer slang instead of the usual '80s works... but still manages to be just as bad (or So Bad, It's Good), with his constant shouting of "lamer" and "ownage". They even lampshaded it:
Headmaster: I am so l33t! Optimus Prime: Yeah? Well, I have no idea what that means!
The worst part about this? Isaac Sumdac (a robotics professor in his 60s) has tried to adopt "Total OWNAGE, N00b!" when using the Headmaster unit as his personal catchphrase. It's hideous and it's a good thing that Megatron stopped him.
In Beast Wars, Cheetor began the series as a version of this, constantly saying things like "Ultra Gear!" and other radical things. The writers and the voice actor all hated this, and the lame dialogue largely went away by the end of the first season.
"DreadWING / is punishING / his Gatling gun is ILLIN'!"
To say nothing of the big bad battlin' Bruticus. (Some forget, but it is in fact Onslaught who is the metamorphin' dudicus.)
Chef describes a variety of words used in lieu of "house", such as "hizzy", claiming that blacks are changing the word to keep white people from using their slang. Eventually, the word for "house" is "flippity floppety floop". Which Mr. Garrison (at that point a Flamboyant Gay) immediately steals, much to Chef's chagrin. It severely chagrined my dazzle as well.
In the beginning of the episode "Butt Out!", an anti-smoking group performs at South Park Elementary, trying (and horribly failing) to reach the kids this way. When they tell the kids that, by not smoking, they can be "just like them", the boys look at each other, horrified, and the show cuts to them chain-smoking behind the school as if their lives depended on it.
The episode ""New Kids on the Blecch" features **NSYNC doing a self-parody in which every other word out of their mouths is either "square" or "old-school".
Bart Simpson's image in early 90s pop culture can be seen as Totally Radical, even though this was never really part of his persona in the actual show (his skateboarding in the opening sequence perhaps being the closest he ever came). The episode "Bart's Inner Child" parodied this phenomenon, right down to the quoting of "Cowabunga". When popular perception of the show began to focus more on Homer's antics, this aspect subsided.
Even lampshaded a few times such as at one point when Bart tries to show he's still cool by singing and dancing to the "Do The Bartman" song. Ralph comments "That is so 1991." Another one had Bart complaining about Lisa using his old "Don't have a cow man" catchphrase to his mom. Marge retorts he doesn't even use it anymore.
Parodied by Poochie, a cartoon dog with "attitude" who's the kung fu hippy from the gangster city. It had the opposite effect the in-universe producers were going for.
Avatar: The Last Airbender has an in-universe example: When Aang is in the Fire Nation, he tries to blend in by using 100+ -year-old slang that gets him all kinds of odd looks. Imagine someone nowadays saying "Bully!" to mean "Awesome!" That's how Aang looked to the rest of the Fire Nation.
Mr. Krabs asks his daughter Pearl if he's still cool. Pearl responds that the word "cool" is no longer considered hip, and that kids now say "coral". The minute Krabs starts saying "coral" (he pronounces it "corral"), Pearl calls her friends to tell them that "coral" is definitely out. Meanwhile Pearl and her friends themselves sound like stereotypical eighties Valley Girls.
Also parodied in a later episode; Patrick, upon getting tanned, remarks that he feels like one of those hip young folks from the soda commercials. Cut to a live-action sexagenarian drinking from a can of soda on a psychedelic background, with dramatic zooms and loud rock music, while an announcer screams about how "radical" the drink is.
Gwen: I'm at one with the cosmic mana, feeling the energy of the universe flowing around and through me.
Likely a subversion, as "groovy" is 1960s slang, and Ben's probably making the point that Gwen's coming across like a New Age hippie. Unless Ben's just an Evil Dead fan, that is...Which is entirely plausible.
Disney Channel's American Dragon Jake Long is chock-full of awkward attempts at writing circa-early-nineties skater-boy talk among the lead Token Trio. It got toned down in the second season and was even called outdated by his sister. It was half-deliberate. The writers originally wanted Jake to slip into progressively worse slang when he was about to do something stupid or morally questionable, but Disney missed the point and made them scale it up the rest of the time too under the delusion that this would make it relevant to children. Then they yelled at the writers at the end of season one when they actually read reviews criticizing the overused slang and made them tone it down in the second season. It ended up pretty close to where the writers wanted it all along.
Batman Beyond largely averted this trope by sticking to Future Slang, but one splicer's warnings to not "diss" him stuck out like a sore thumb in the second season premiere.
Parodied brilliantly in the Batman: The Animated Series / The New Batman Adventures episode "Mean Seasons," one of whose scenes shows a group of network bigwigs pilots:
(kid with backwards baseball cap and shades skateboards up to the camera, pulls out a police badge):
Kid: "You're busted!"
Announcer: "Teen Cop: inner-city street drama with a fresh attitude."
Lampshaded when Professor Utonium makes himself a super suit and joins the girls on their missions. He uses slang, but it's the slang from when he was a kid. The girls react appropriately.
Professor Utonium: Bring it on, daddy-o.
Mojo Jojo: Oh that is so lame. You will pay for your use of inappropriate dialogue!
Then there the knock off PPG in "Knock it Off" especially in the case of Buttercup's clone "Girl Power".
The twins from Superjail! seem to fit into this category.
Danny Phantom suffers from this quite a bit. Especially with its rampant use of the word "waste".
Danny wasn't nearly as bad as Master's Blasters, though.
Mr. Lancer's book "How To Be Hip" that must be decades old. Even the kids at Casper give him weird looks and leave when he tries to talk to them from it.
To say nothing of Sidney Poindexter. To give you an idea, he's from the '50s.
In one episode of The Tick, where the villain was a super-intelligent child, the Tick attempted to relate with him by talking like this.
Futurama simultaneously avoids and parodies this trope: The youngest adult main character, Amy, uses semi-current slang with science-fictiony add-ons (For example, shmeesh=yeesh, splech=yech, guh=duh, etc.)
It goes a little further than that. For example, people (not just Amy) in the future say "we're boned" instead of "we're screwed." (But considering what 'boning' meant already...) And of course "ask" has been completely replaced by the slang "axe".
Which is almost ironic, as "axe" was how English-speakers said "ask" in Chaucer's time.
Conventional totally radical speech was parodied by That Guy in the episode "Future Stock". He was awesome... awesome to the max.
In Roswell That Ends Well (set in the '40s), Leela goes all over the map with her 20th century slang ("What's up, Holmes?")
Spoofed in Johnny Test with Bling-Bling Boy, a rich jerk who's Johnny's recurring nemesis. He came up with the name in an attempt to be cool. A Running Gag is when people refer to him by his first name, he insists that you call him Bling-Bling Boy. It was eventually dropped when the characters learned to humor him. The show itself is full of this, giving it a bizarre late-90's type of atmosphere.
In an episode of Garfield and Friends, Jon's teenaged niece talked like this and Garfield and the narrator had to do translating duties every time she spoke. Eventually, poor Garf' started talking this way himself. (The sound of Lorenzo Music uttering "Gag us with a spoon, dude" in that famously dreary voice of his is undeniably a hilarious moment.)
Boomerang's promo spot for their "Meddling Kids" block spotlights a clip of a character from Jabberjaw saying "Wowwy-wow-wow!" as an example of "the lingo."
Played straight andinverted at the same time in Disney's The Aristocats: The movie had Scat Cat and others saying "groovy" and "cat" in a film released in 1970 (when that kind of slang was going out of style), but the film itself was set in 1910, when none of such slang was in common use (or even invented) yet. Of course, the movie had swing to begin with...
Still counts, because that sequence also has the titular kittens (who are, as their name suggests, supposed to be Upper Class Twits) awkwardly joining Scat's crew in singing the jazz song "Ev'rybody Wants To Be a Cat." (Note that the song contains plenty of beatnik/hippie slang such as "square" and "where it's at.")
On an episode of Jimmy Two-Shoes, Lucius tries speaking in slang during a commercial for his cologne. Jimmy notes, "It's almost cool how uncool he is."
May double as Actor Allusion, as Chris' voice actor also did Jude on 6teen, who made heavy use of this trope himself. However, in both cases, they were done fairly well.
Geoff speaks in this, while Ezekiel offen attempts it with no success.
Adventure Time loves coming up with deliberately goofy slang, such as "mathematical" and "algebraic". Largely justified, in that it takes place in a post-apocalyptic world, meaning that the characters' understanding of slang would be taken from the movies, video games, and other entertainment that remained after the Great Mushroom War.
Party Pat: "that monster's gut was totally excellent".
Lumpy people have "lump/ing", "buumps", and overuse contemporary slang like "totally", "whatever" and "awesome".
Quack Pack, a mid-nineties reboot of Huey, Dewey and Louie, stated, in that obnoxious talking bubble-tape voice, that "they're not kids anymore. They're EXTREME TEENS!!!!" Followed by one of the ducklings riding a skateboard saying "Ex-treme!"
On Toot & Puddle, the characters will sometimes say "Gee whilikers!" which surely went out of fashion sometime around the 60s.
Parodied in Invader Zim with Poop Dog, the gangsta spectre of defeat!
Poop Dog: Hey kids, do you wanna go magnet wit da monies?
Child: What does that mean?
This goes on to the point where even he himself can't take it.
Poop Dog: And if you think you somethin' with the top sellies and... I can't do this.
Happens to some extent in the Young Justice cartoon. For instance, Artemis insults Kid Flash by calling him "Baywatch", a reference to a TV show that ended when she would have been around 5 years old.
Widget The World Watcher and Mr Bogus (both from Zodiac Entertainment) are guilty of abuse of the word "awesome" in their opening titles (compounded by the latter dragging in "bodacious"), which get in the way of their otherwise awes- good theme tunes by Dale Schacker, who wisely avoided such slang with Saber Rider and the Star Sheriffs.
Parodied when Rainbow Dash insists that her pet must possess "coolness", "awesomeness" and "radicalness". When Twilight Sparkle points out those three mean the same, she is given an Affectionate Gesture to the Head by Rainbow.
Gilda from Griffon The Brush Off was this so bad that it hurt. It's quite possible Rainbow Dash learned this from her, since she talked in nothing but Totally Radical for the entirety of her episode (complete with guitar riffs). Of course, since the viewers were supposed to dislike her, it actually worked out.
Miss Grotke on Recess often makes use of outdated slang.
Judy Jetson in the 1980's revival of The Jetsons fits this trope to a tee, even going so far as to follow this trope when talking to her own mother!
Super Friends. In the first episode of the 1973/74 season, "The Power Pirate", Wendy and Marvin spoke like 60's hippies, regularly used terms like "groovy", "cool", "right on" and "far out". Apparently the writers figured out how silly this sounded and they didn't speak like this for the rest of the season.
While most of the characters in Looney Tunes were no strangers to using slang that is now considered dated, the one major stand-out is their last recurring character, Cool Cat, who reflected on the beatnik culture of the time and frequently used terms like "groovy" and "baby". Because of this, and his Limited Animation art style, he's considered even more dated than Bugs or Daffy despite debuting nearly 20 years later. As a result, he's seldom used today.
Even at the time he was outdated. He debuted in the late 60s, when beatniks had gone out of fashion for the hippies.
My Life as a Teenage Robot: In one episode Jenny reads a slang book in order for her to fit in, only for her to realize that the book was published in 1983. Gnarly! Taken even further in the same episode, when a strange person finding an opportunity to chat note actually Vexus in disguise speaks in 1920s slang.
In Ed Eddn Eddy, local biker and skateboarder: Kevin. His love interest, Nazz to a lesser extent.
Dude, That's My Ghost! (if the title didn't tip you off) has this in spades, mostly hinging on cool-sounding puns, nicknames and incredibly, achingly "cool" voicework where you're not sure if it's parody leading the dialogue or a very lost sense of how people speak.