High School Hits From The '90s That Prove Gen X Is The Coolest By Far

Imagine a time when folks actually understood that "cool" meant not trying to be cool, not begging for attention, and not endlessly whinging about practically everything. "Cool" was a big middle finger wrapped in flannel that sneered in the face of dull establishment goons, judgmental peers, and petty powers that be. This, plus more, was high school in the '90s at its best, Gen X at its best, and Gen X's formative music at its best. This is also why so many '90s hits prove that Gen X was the coolest generation of all.

But how do we choose songs that typify '90s coolness? We start with the definition of "cool" itself — the aforementioned attitude, a willingness to shrug off trends, being comfortable in your own skin, etc. — and look for songs that reflect those sentiments. We've also got to choose songs that could have only come from the '90s zeitgeist. Additionally, these songs have to triangulate on Gen Xers (born 1965 to 1980) who were high schoolers in the '90s. Finally, even though the '90s was a time of immense musical eclecticism that encompassed everything from grunge to G-funk to Sarah McLachlan, we're going to focus on the flavor of the age and not a checklist of genres.

On that note, there are so, so many songs to choose from that we've got to omit about 99.999% of them. Readers should take our list as a sample, not gospel. That sample includes smash hits from Rage Against the Machine and Soundgarden, standout tracks like "Banditos" from The Refreshments and "Loser" from Beck, plus a surprise choice from R&B outfit En Vogue.

"And everybody knows / That the world is full of stupid people / Well, I got the pistols, so I'll keep the pesos / Yeah, and that seems fair." Pretty much, Roger Clyne of The Refreshments, yep. Also, what other song besides the group's 1996 hit "Banditos" from "Fizzy Fuzzy Big & Buzzy" drops some proper nouns about "Star Trek"? "Well, give your ID card to the border guard / Yeah, your alias says you're Captain Jean-Luc Picard / Of the United Federation Of Planets / 'Cause he won't speak English anyway." These lyrics are worth quoting at length just to illustrate how squarely cool and "we are who we are" "Banditos" was and is, much like the decade that spawned it.

"Banditos" comes from the minds of The Refreshments, aka, the band that did the OG "King of the Hill" theme song, "Yahoos and Triangles," which debuted in 1997, the year after "Banditos" blew up. The song sits squarely in what we might call the "dork core" arena of '90s punk-laced, post-grunge pop-rock (think: Weezer), and the song echoes the same societal disillusionment as tracks like 1997's "Flagpole Sitta" from Harvey Danger ("Been around the world and found that only stupid people are breeding / The cretins cloning and feeding"). Similarly, it does so in a jokingly sneering way that produces a helluva catchy tune.

All in all, the above information reflects the '90s coolness cred on multiple fronts: "Banditos" is a superb musical exemplar of its time, could only come from its time, and drops references to one iconic TV show while presaging the music for another. And of course, it comes equipped with all the attitude and energy you'd expect from the best of Gen X music. Yeah, that sounds about right.

Anyone who gazes upon Beck and thinks, "Hey, this guy's song is named 'Loser!' He's not cool," is to be mourned. They're absolutely missing the point of lyrics like, "Butane in my veins, and I'm out to cut the junkie / With the plastic eyeballs, spray-paint the vegetables / Dog food skulls with the beefcake pantyhose." Say what, you ask? Exactly.

Few songs embody the stereotypical "Meh, screw it" Gen X vibe pervading much of the generation's formative, MTV-laced years as Beck's smash hit "Loser" from 1994's "Mellow Gold." Few songs embody the weird musical melange of the '90s, too (NPR described Beck as a "hip/hop folk rocker"). Even fewer do so while launching an entire career and serving as a quintessential rags-to-riches story. After all, Beck wrote the song "living in a shed behind a house with a bunch of rats, next to an alley downtown" in New York City while "alphabetizing the pornography section" of a video store for minimum wage, as he told Rolling Stone. He recorded his music on tape and circulated "Loser" through college radio on cassette. That really couldn't happen anymore and is imminently '90s. 

Musically, "Loser" isn't just a joke track, either. The rousing slacker anthem caught on with the zeitgeist in a big way that speaks to the unique self-awareness of the '90s: "Soy un perdedor / I'm a loser, baby, so why don't you kill me?" This chorus is made extra fun because "perdedor" in Spanish just means someone who loses, like a contest — not a "loser" in a colloquial sense. Neither are true for Beck or Gen X, though.

The '90s wasn't all about grunge, but the Seattle scene's post-punk musical stylings undeniably left their DNA all over the decade. Stripped-down, raw, rough, authentic, self-reflective, vulnerable, and defiant in equal parts: All of this and more can be said of grunge. And since we'd be remiss to not choose one song from a cadre of grunge-defining '90s hits to stand in for Gen X's coolness, we're tipping our hat to "Black Hole Sun" from Soundgarden's 1994 album "Superunknown."

"Black Hole Sun" is at once indicative of its time and also an extremely unique musical beast, both for Soundgarden and for grunge as a whole. It's low-tempo, slow-building, dreamy, and floaty, with lots of space in the mix as it swaps time signatures from 4/4 to 9/4 and employs very unusual chord structures. "Black Hole Sun" dared to be different from its peers, and it was a massive hit.  

"Black Hole Sun" also perfectly encapsulates the outlook of '90s youth culture. This is true not only of its lyrics — "Hang my head, drown my fear / 'Til you all just disappear" — but also of its extremely memorable music video. The cinematic shows all the world's vapid suburbanites and sectors of empty life sucked into a world-destroying sun with a black hole inside (which, by the way, is theoretically real). Could any grumbling '90s high schooler actually cope with such an event? Probably not. But such sentiments were a reflection of the times, i.e., a rejection of social norms in the face of the blinding economic and social prosperity of the '90s. This duality of external prosperity vs. internal discontent belongs squarely in the '90s Gen X experience. It's a juvenile kind of "cool," yes, but it was the definition of cool, nonetheless. 

Speaking of songs and bands that could have only come from the '90s — no matter how universal and ever-relevant their music is — we've got Rage Against the Machine. Funk, rock, metal, hip-hop: Rage blend it all together into a one-of-a-kind wrath bomb (or "Bombtrack," as the group might say) that rattles the teeth out of your head as much as it rattles some sense into it. And few songs do this as potently as "Bulls on Parade" from from 1996's "Evil Empire."

"Bulls on Parade" represents the best of Rage in a way that's absolutely iconic of '90s coolness. Take Zack de la Rocha's toothy yowl, layer it atop a precise, flowing pocket, and weave in Tom Morello's weird string-scratching wizardry, and you've got the king of genre-agnostic bangers that still sounds cutting edge today. Plus, "Bulls on Parade" has got bars for days: "What we don't know keeps the contracts alive and movin' / They don't gotta burn the books, they just remove 'em / While arms warehouses fill as quick as the cells / Rally 'round the family, pockets full of shells." Come on. If this song doesn't make you want to stomp around and smash stuff, it's time to check your pulse.

Much like "Black Hole Sun," "Bulls on Parade" came from a prosperous era, and it might seem odd to view this song in light of the "external prosperity vs. internal discontent" duality we cited. But maybe there's no better opportunity to think about social issues than when everything is going fine, at least because there's headspace to do so. That's yet another reason why '90s high schoolers grew up in the coolest of times.

What if we told you that one of the sickest, most anthemic '90s rock riffs and songs came from an R&B quartet known for lush, four-point harmony and choreographed stage dances? That might be enough for some Gen Xers to remember "Free Your Mind" by En Vogue from the group's 1992 album, "Funky Divas." If you haven't heard this hit or seen its music video, get on it. "Free Your Mind" roils with so much uncompromising, in-your-face attitude, killer grooves, and stank face-inducing guitars that an entire generation's got the right to be proud of it.

"Free Your Mind" typifies the coolness of the '90s in plenty of ways besides its attitude, though. It's another cross-genre work that chucks the prejudices it describes out the window, right down to its bold use of rock conventions. Speaking of such prejudices, the song is equally up-front about its subject matter, with lines like, "I might date another race or color / It doesn't mean I don't like my strong Black brothers," and its chorus, "Free your mind and the rest will follow / Be color blind, don't be so shallow." Also, the song's music video seriously looks like it influenced the Wachowskis' leather-clad, gothic-industrial look for 1999's "The Matrix." Bonus points for that.

En Vogue member Cindy Herron might have best summarized '90s music, outlook, and Gen X in general in a behind-the-scenes interview on YouTube about "Free Your Mind." "The message is one of love and peace and unity and letting go of those old bad habits that so many of us have and just accepting everyone and people for what they really are," she said. "And it's about having fun, too." Is there anything cooler than that?