When Charli XCX and Troye Sivan dropped their collaborative single “1999” last fall, I didn’t think much of it. (Initially, anyway.) Coming off of an incredibly strong 18-month run for both youthful and youth-focused artists, the song’s punchy synth designs and adolescent wistfulness seemed like an intentional trifle — just a bit of low-stakes fun, as ephemeral as the collective swell of nostalgia that’s constantly ebbed and flowed throughout pop culture over the past decade.

This was all before the video dropped, of course: accompanied by a sensory assault of decade-specific references akin to the history-of-humanity montage that emotionally devastates Leeloo in The Fifth Element, “1999” was effectively given a new lease on life to the point where it charted in the multiple European countries — a sensation that Charli hadn’t experienced since the previous year’s “Boys.”

The hall-of-mirrors meme-ability of the “1999” video kept it from being forgotten, and you could say the same about some of the biggest pop hits that actually came from that year, too. If you’re internet-native, memes related to songs from 1999 are likely to pop up with regularity in your feed.

Sometimes, the songs are mentioned to bolster context; consider the platform-defining and since-deleted tweet from Twitter user @intellegint in which “Buzzfeed Jenny” apologizes for singing Lou Bega’s binders-full-of-women anthem “Mambo No. 5″ at your dad’s funeral, with a subsequent faux-“reply guy” reply.

Smash Mouth’s “All Star” (released 5/4/99, twenty years ago this weekend) has been the subject of endless meme-ery, to the point where the band themselves have their own favorite “All Star” memes.

And if you were ever in any danger of forgetting Santana and Rob Thomas’ supermarket-dominating “Smooth,” an endlessly-retweeted meme has doubtless lodged it in your memory.

MAN ITS A…. HOT ONE pic.twitter.com/GZ2US61BIP

— uglyass noodle head (@corihealey) July 26, 2016

It’s easy to write this micro-phenomenon — a digital occurrence that’s rippled throughout the decade, especially as our collective fluency in meme language has strengthened both by necessity and design — the work of pure nostalgia. After all, nostalgia has been the driving force in 2010s popular culture at large, from the endless stream of reboots/prequels/sequels hitting the multiplexes to era-redolent works like Stranger Things and the found-footage, warped-VHS aesthetic that permeated early-2010s indie via the dual vessels of chillwave and witch house. Nostalgia can often reflect a point of erosion in which new memories of old artifacts overpower true points of cultural origin — which certainly explains why so many “All Star” memes have become part-and-parcel with Shrek memes, despite the fact that the song was originally affiliated with the Ben Stiller-starring superhero comedy Mystery Men.

Some credit (or blame, depending on your outlook) for the cultural endurance of these three songs — all a year shy of US drinking age this year — in the digital age is due to the musicians themselves possessing just enough good humor and self-awareness to make it so. The internet doesn’t always take kindly to the respective butts of jokes attempting to transition from butt to joke-teller, but Thomas’ Twitter and the overall confounding odyssey of Smash Mouth in the digital age — a weird omnipresence that’s encompassed Car Seat Headrest collaborations, unprovoked takes on the gender politics behind oral sex, and an “All Star” musical — are both sterling examples of adding just enough of your own spice to the meme-stew without overpowering the communal flavor.

And they aren’t the only artists whose singles from 1999 have retained a level of staying power due to pure referentialism. The titular refrain to Britney Spears’ “…Baby One More Time” is featured prominently in the choruses of “1999” and Anne-Marie’s Ed Sheeran-co-penned “2002”; Shania Twain’s iconically blasé titular utterance from her “That Don’t Impress Me Much” has been meme-ified to throw side-eyed shade at topics ranging from religion and war criminals to the purported inventor of Bitcoin and the act of making memes itself.

Hey, did you ever think about how old the unborn child in the video for Len’s eternal Song Of The Summer “Steal My Sunshine” is now? Well, now you are — and this is all without arguing the meme-situated semantics of Blink-182’s “All The Small Things,” the visual treatment of which treated its own cultural surroundings as a 1999-set “1999,” effectively making for a pre-meme culture meme-fest.

On its face, it seems strange that so many pop songs from 1999 — more than any other year in its proximity, arguably — have proved such ripe fruit for our memelords. Some of these songs are objectively terrible (sorry, “All Star”), some still enduring and sturdy (I see you, Shania), all of which nonetheless critically cherished just enough at the time to chart on that year’s Pazz And Jop (a good list to have in your back pocket the next time someone claims critics can be too snobbish).

Alex Turner de #ArcticMonkeys vuelve a hacer de las suyas en un karaoke. Ahora interpreta 'Smooth' de Santana y Rob Thomas pic.twitter.com/eijZUrpBKC

— Binaural (@binauralblog) July 30, 2017

But like so much that washes out in the internet’s spin cycle, the selective focus seems truly random, resulting in the accidental elevation of music that largely otherwise wouldn’t have stood the test of time. Unless you count Smash Mouth lead singer Steve Harwell’s quasi-doppelganger proximity to Guy Fieri, there’s no clear cultural throughline that explains why the mere referencing of these songs have proved humorous to anyone at all.

1999 Collaboration Between Carlos Santana, Rob Thomas Somehow Standing Test Of Time http://ow.ly/15ZDYz

— The Onion (@TheOnion) November 5, 2009

I made an album using only samples of Smooth by Santana ft. Rob Thomas https://t.co/kHyayXQXCM

— jetski (@jetski0) June 29, 2018

This is where age comes into play, though. Going back to “1999” for a second: Charli and Sivan were both seven and five years old, respectively, in the year they sing the praises of, and the Gen Z’ers born during that year are just cracking open the third decade of their existence. To someone who possessed a level of cultural awareness in 1999 — we’re talking the bare minimum of being able to turn on MTV by yourself and watch it for hours on end — these musical artifacts are bland, banal, and totally bereft of what large swaths of discerning adults refer to as “taste.”

If you’re 20 years old or younger, however? Smash Mouth are a bunch of theme-restaurant doofuses wearing huge shirts, “Mambo No. 5″ is hilariously corny, and there’s a bunch of giggles to be had at the mere utterance of, “It’s a hot one.” An element of the past that will remain increasingly true as social media and shitposting culture continues to get trippier and more unnavigable is that for every one adult who sees the past as a boring thing to be left behind, there’s 10 kids bored in homeroom looking to distract themselves with Shrek GIFs and reverse-engineered “Bawitdaba” references before the next active shooter drill takes place.

Ultimately, it’s more interesting to consider the future of memes under this 1999-reflecting lens than it is to analyze the possible causes for their presence. Theoretically, there’ll be plenty of pop cultural fodder for future youths to draw from when our past-pilfering tendencies reach the late 2000s — a time in which the Disney stars of yesterday were not quite yet the public and troubled figures of today, exuding a level of corporate faux-earnestness that will likely prove malleable to purveyors of distanced irony in years to come. But much of popular culture in the 2010s — especially the realm of pop, once considered with a disposability that arguably led to meme culture itself — has experienced a trifurcation between Serious Art, insta-meme masterminds drawing from the present, and deep-dive nostalgia for sounds and styles from the ‘80s and ‘90s. The dullness that was pop music in 1999 simply doesn’t exist in our current cultural landscape — and what’s the point of laughing about that in the future?