Linkara in Atop the Fourth Wall gets to parody this through his persona of "90's Kid" - a flannel and backwards-baseball-cap wearing teen who's obsessed with Nirvana, Rob Liefeld, and Doom.
Climate Town: One of the natural gas advertisements Rollie mocks is an incredibly awkward and long commercial with young adults rapping about natural gas in an attempt to make young people like and fight for natural gas.
"Joey, stop trying to turn 'Brooklyn Rage' into a Catchphrase."
Also the first and only language of Jaden Yuki. "This shit be ballin'!"
And again when there's a cut to the Singapore dub. "Tubular idea, Pharaoh!"
Andrew Ti's blog Yo, Is This Racist? frequently uses '90s hip-hop slang as part of the author's persona. There are about as many posts critical of wackness as there are of racism.
Knuckles of Sonic The Other Movie peppers his dialogue with '90s slang in an attempt to look cool. Only Tails is impressed.
Rhett & Link have done this intentionally with their rap videos. The best example is Phatdippin', or going swimming fully dressed.
Parodied on Geoffrey Chaucer Hath a Blog. At one point, the Lords Appellant take over the blog and rebrand it as ''Geoffrey Chaucer Hath an Extreme Blog! Go England! It Is Rad!"
The Nostalgia Chick makes a Running Gag of this in her Sister Act review, referring to the choir's "Urban Gangsta Flava!" Also used when she talks about TLC in another review. She's talking about their appeal to white audiences during a part featuring an actual black guy, and he says he thinks it was because of their, say it with us now, "Urban Gangsta Flava!"
Also comes up in her "Least Awful Disney Sequels" review:
The recaps on the Goosebumps blog Blogger Beware have a "R.L. Stine Is Down With The Kids" section which makes fun of the books' many dubious depictions of children's slang and activities.
In Dragon Ball Z Abridged, Cell tries to get 18 to let him absorb her by projecting an image of her brother trying to convince her to "get all up in Cell" by telling her "it's downright tubular in here." However, considering Cell's version of 17 sounded as stereotypically 90s as you can get, she's not fooled at all.
18: Wow, you really know nothing about us.
Cell: Well, to be fair, I did just meet you.
In an advertisement for an upcoming Game Grumps charity livestream, Arin embraced the Totally Radical attitude for laughs, completed with a 4:3 screen ratio and a rather bad image definition.
"Tubular! Everything's tubular!! Made with TUUUUUBES!!!"
Shmoop is basically what Spark Notes would look like if it were written entirely in this style. As far as we can discern, yes, they are serious in doing so.
An episode of RWBY Chibi has Taiyang acting this way, complete with skateboarding and a backwards baseball cap, after he gets jealous of his daughters admiration of their Cool Uncle Qrow. No one thinks it's cool.
Joueur du Grenier: Papy Grenier recounting his time as CJ (using the French slang called verlan where a word's syllables are inverted):
Papy Grenier: Well, okay, it was JC, short for Jean-Charles, but I switched it around to be more "street"!
Grandchild: Gramps, shut your face, right now.
Papy Grenier: Aw.
Spectrum Pulse fell victim to this when Mark talked about the song "What Does The Fox Say?" by Ylvis, stating that the furries had answered the question: The fox "yiffs". While in the fandom foxes are stereotypically known for yiffing, he got the term completely wrong: "yiff" is furry jargon for having sex.
In SMPLive, VoiceOverPete tends to fall into this due to being the oldest member of the server and someone who isn't super aware of modern slang and memes. He will frequently overuse or misuse slang and tends to refer to the other players as "gamers".