#3. Billy Gilman and Rosie O'Donnell: "Santa.com"
In 2000, the entire world was blessed with the most baffling Christmas song in recorded history in the form of 12-year-old country star Billy Gilman singing about emailing Santa Claus via his "worldwide address," a phrase that is dusty even for the Clinton administration:
Old man Santa's in a brand new age
With a worldwide address and his own Web page
Got a high-tech computer with a million megabytes
Pickin' it up with his global satellite
I'm sending it out h-t-t-p
You've gotta get this letter ASAP.
"That guy made me sing it! Hand me the doll -- I'll show you where."
In the video, little Billy belts out hackneyed Internet references through the fangle-toothed jungle in his mouth while Rosie O'Donnell does her best to ride his coattails into a future doubtless paved in sunshine and victory (spoiler: it wasn't).
So, Billy is in a rush to get his Christmas list to Santa, because for some reason a 12-year-old boy just had too many things on his schedule to allow time to demand free gifts from a fantasy character he shares no other type of contact with. Billy then asserts that Father Christmas will be receiving his message via global satellite, which suggests that he doesn't entirely understand how the Internet works, although Santa would probably have to have some kind of crazy expensive 4G plan to check his Gmail from the North Pole.
In the very next line, Billy delights us all by pummeling the acronym for hypertext transfer protocol into catch-all slang for using the Internet ("I'm sending it out h-t-t-p"), vernacular that had not, at that point, ever been adopted by anyone outside of him and his Bob Newhart Christmas sweater (indeed, it has not been used by anyone since, other than by the Black Eyed Peas in the song we mentioned at the start).
Remember, this is a kid who was raised during the initial worldwide explosion of this technology, yet he sounds about as comfortable with the terminology as every white person who saw Rosewood in the theater was with their evening. If you're 12 and already that clueless about modern technology, you might as well just pack it in and retreat into obscurity, which is precisely what Billy Gilman did.
We don't think it's making a huge leap to say it was totally because of that jacket.
#2. T-Pain, J-Shin, and Tila Tequila: "Send Me an E-Mail"
T-Pain and J-Shin collaborated on this song back in 2006, and judging by these lyrics, it seems to be about a douchebag and his haunted computer:
Two o'clock in the mornin', I'm sleepin'
And something wakes me but I don't know what it is (You've got mail)
It's my ex, prob'ly just misses my sex
Lemme get up and see what the deal, what the hell
It's cryin' faces all over my screen
And a picture of her eye
Try to tell myself this ain't nothing to LOL about.
"But I did. I did LOL about it."
After being inexplicably woken up by an email message (which we're guessing has happened to exactly zero people currently reading this article, because that is not how email works), J-Shin checks his Myspace to see a billion pictures of his weepy ex-girlfriend, heartsick over the breakup for reasons we cannot understand.
To be fair, this is a scenario that still occurs today (albeit now on Facebook), but nothing dates your rap opus quite like peppering it with cameos of Tila Tequila, a Playboy model who was briefly famous in the mid-2000s for having, like, seriously, a ton of friends on Myspace. This particular skill was difficult to monetize (because it is completely worthless), so she was clumsily shoved into television and movies by ill-advised producers trying to catch some of that "Hey, here's that lady from that thing you kids like" magic.
Future civilizations will assume that her existence proves that troll dolls were also a real species.
J-Shin delivers a few more lines about emailing this girl back and forth, including the phrase "you've got mail," which you may notice was disqualified from rap lyrics back in 1998 by Tom Hanks and Meg Ryan.
Then T-Pain takes the keyboard away from him to type out a reply to set this girl straight, and accidentally delivers the greatest moment in the entire song:
What the deal?
Why you actin' like a n***a wasn't street?
Why you actin' like I wasn't sweet?
Why you actin' like I didn't sweep you off your feet?
Why you actin' like a n***a didn't wanna take you out to eat?
Sometimes, the crowd just stops and stares while T-Pain goes on, oblivious to their confusion.
There's no forced Internet reference here. That last line is just too hilarious not to mention.
#1. Nikki Cleary: "I.M. Me"
Thirteen-year-old Brittney Cleary released "I.M. Me" back in 2002, before she was forced to change her name to Nikki because her label already had Britney Spears under contract and feared a collective brain implosion should two Britneys ever happen to grace Total Request Live at the same time (these fears turned out to be both unfounded and wildly optimistic). And while Britney Spears' first album did feature the timeless classic "E-Mail My Heart," we argue that the Rebecca Black precursor "I.M. Me" is infinitely more terrible. Without hyperbole, it is probably the worst thing to ever happen to the Internet, because it is a 100 percent factual representation of just how fucking stupid the Internet can be:
Let's meet at the same time
Send your jpeg, I wanna see your face
Girlfriend, send an I.M.
"Hold on, I gotta wait for my mom to get off the phone so I can use the computer."
No time to spell
Oops, there goes that little bell
Bye, bye for now
Hey, LOL, G2G
I gotta go, but baby watch for me 'cause
I'll be right back, BRB
So sign on, and I.M. me.
Your monitor isn't on, you fucking idiot.
Mom thinks I'm doing homework
But I can't help it, I've just got to surf
I gotta chat with my girlfriends online
We're digital divas
This Girl Wide Web is hot stuff
My buddy list is growing all the time
I got a Web page
Sign my guest book with your screen name
Check it out, then send an I.M.
What's your profile?
This is just like passing notes
It's easier to type than use a pen.
Nikki punches us in the face with AOL Instant Messenger references (which was experiencing the height of its popularity at the time) while confusingly addressing both her girlfriends and someone she insists on calling "baby" at random intervals. That's the whole song, by the way -- just singing about talking to people online about absolutely nothing in particular. There's a hip-sounding buzzword in literally every line of the song's four-minute duration, which is impressive considering that HOLY GOD, THIS GOES ON FOR FOUR MINUTES?
Even though she assures us that there's "no time to spell" (and really who would want to, what with typing being easier than using a pen?), Nikki still breaks down her favorite acronyms for us, many times over, lest we be lost in a fog of confusion and unable to follow along. The worst thing is, she isn't wrong. Every single text-speak acronym she rattles off is totally correct, situationally appropriate, and still being used a decade later by people twice her freaking age.
"Hahaha! Oh, Jim, your use of youthful slang makes you interesting!"
Her prescience isn't without its limits, though. She falls into the same trap that everyone else seemed to back then and tries to make up her own slang -- the "Girl Wide Web" never caught on. That's probably for the best, because we are certain that if you type "girl wide web" into a search engine, the results will in no way resemble whatever Lizzie McGuire bullshit that 13-year-old girl was singing about. Also, nobody has signed a guestbook since 1997, and this song came out in 2002. She might as well have thrown in a lyric about the frames on her Angelfire page. Nice try, Nikki. Now aren't you glad you didn't release this under your own name?