The 1980s might also be the decade that pop culture became self-aware for the first time. The watershed example is The Simpsons, of course, but even some earlier works that don't lean on pop culture for satirical purposes were beginning to get in on the act. Back to the Future has a rich undercurrent of cultural references that define both the home world at the start of the movie (California in 1985, home to '80s-tastic protagonist Marty McFly) and the world he travels to (the same town in 1955, home to his teenage parents). A judicious use of pop culture makes the movie more real.
By the time I was watching TV and movies in the 1990s, the ability to reference pop culture had turned into something of an obsession, culminating with the debut of Family Guy in 1999. This was a show that eschewed the integrated pop culture references of The Simpsons in exchange for sight gags and cutaways that allowed the writers to do virtually anything they wanted at virtually any time, a sensibility that has carried that show through good years and bad. When Family Guy was renewed from cancellation, it was a victory for the show's random style, which has since become a definitive characteristic of Internet humor. And that might be why, for all its flashing colors and hectic pacing, the video at the top of this page strikes me as refined.
Arin "Egoraptor" Hansen - lead animator on the video and part of Starbomb, the group that performs the song - is Internet royalty. I first encountered his works in the middle of the last decade at Flash repository Newgrounds, where he had already garnered an impressive reputation for the "Awesome" series. These were videos in which he would deconstruct a video game at a rapid-fire pace. Here's Metal Gear Awesome, which was the first video he published on Newgrounds. This one is also not recommended for work:
Egoraptor later became the cohost of a web series called Game Grumps that I quite frankly can't get into. Listening to two guys crack random jokes over video game footage lacked the visceral punch of rewriting and reanimated the games themselves and using that as a springboard into comedy. (Full disclosure: I'm focusing on Egoraptor because I'm familiar with him. He's joined here by Leigh Daniel Avidan and Brian Wecht, the former of whom is also on Game Grumps, and I know virtually nothing about them, or Rachel Bloom, who sings the part of Peach. There's only so much one man can know about the Internet.)
The Super Mario universe has been broadened considerably since Super Mario Bros. came out, but Luigi's Ballad would still mostly make sense to somebody from 1985 who had played the game. Some visual elements - such as enemies from later games and the references to Mario Kart, which first appeared in 1992 - would get lost, but stylistically the games have remained remarkably similar over nearly thirty years. Perhaps the biggest jump for time-traveling viewers would be the characters' personalities.
Mario and Peach have the sort of weird quasi-relationship shared by Barbie and Ken, or Micky and Minnie Mouse: They're always together, and yet their couple status never seems fully confirmed. We don't get a very good look at their personalities until Super Mario 64, the N64's inaugural game and the first one in which either character speaks. They each get only a few lines (Peach's at the beginning, Mario's looped throughout the game whenever he does anything), but they're enough to give us reinforcements on what we already knew: Peach is a nice person with terrible luck and Mario is a go-getter who is unfazed by absolutely anything. Both of these traits are ramped all the way up in Luigi's Ballad: Mario is unable to stay out of anyone's face about his wants and Peach, while untroubled by his incredibly blunt advances, is too polite to actually choose between the brothers.
Luigi, whose appearance in Super Mario Bros. was as a palette-swapped Mario, has similar in-game characteristics that are ramped down in the song for humor value. He's a nice guy who just wants to do stuff with the girl his brother is also hitting on. The exchange between him and Peach at the song's height is actually kind of beautiful, the idea that these are two people who want to try something, even if they don't know what it is. Mario, of course, ruins all this, but you don't save the same girl from the same bad guy for thirty years without getting a little frustrated.
The immaturity of the subject matter in Luigi's Ballad is a clever rouse: The creators had a fantastic sense of understanding and scope on the source material, as well as how to best bend it to suit the Internet's current sense of humor. That the whole thing manifests itself as a barrage of dick jokes is simply par for the course in this day and age.