I should begin here: During the actual '90s, I was much too busy listening to Japanese videogame soundtracks (educate yourself) to actually enjoy '90s pop music. My first-hand memories of most of it are hearing it in a car, at a skating rink, on somebody else's Discman, and shaking my head in lonely disapproval because the lyrics were in English. I love all of it now -- it feels, in hindsight, like I always have--but I am not the right man for the job of overgeneralizing every pop song from the '90s into neat, reductive categories.
Which is why I'm only going to start doing that. For the purposes of explaining to someone you've just met at a party which '90s music you like; for the purposes of chaos dunking on somebody when they act like their love of Candlebox is as cool as your love of Fastball; for the purposes of having pleasant, dreamy conversations with demographically appropriate companions about songs you first heard in the middle seats of a minivan, I humbly offer a few starter categories for the '90s pop songs you kind of remember enjoying, for use when you and a friend go on a YouTube binge some boring weekend night.
Please add more in the comments, as they occur to you. This is only a start, and I am only one man. One man whose favorite CD in 1999 was the soundtrack to Super Mario 64.
Rust-belt-sounding post-grunge Representative cases: Matchbox 20, Goo Goo Dolls Random, enjoyable singles: Matchbox 20 - "Real World"; Foo Fighters - "Everlong"; Our Lady Peace - "Clumsy"
I don't know if all or even most of the bands who made up this category--hookier and more "sold out" and less prone to solipsism and agorophobia than actual grunge--were actually from the rust belt, but all of the singers blend together, for me, into the guy from all the Yourself or Someone Like You singles: Young and white and in a dead-end job, working through a relationship that isn't very fulfilling, dreaming sincerely of being the "head honcho", living by an interstate exit with a Hardee's on each end.
For all that flyover country angst, though, my favorite examples of rust-belt-sounding post-grunge are the species's most overproduced singles. "Back 2 Good" and all those other Matchbox 20 songs might be about disenfranchised guys, but they're produced in full-on adult contemporary mode. And I love it.
Jammy acoustic pop-rock Representative cases: Hootie and the Blowfish, Sister Hazel, Dave Matthews Band Random, enjoyable singles: Hootie - "Hold My Hand"; Blues Traveler, that Blues Traveler song
This is a broad category, and I think scientists down the line might break it up into two subspecies--the Hootie side and the Dave side. The Hootie side is... rootsy, maybe? earthy? but otherwise content to strum through big, acoustic, hooky singles about being slightly quirky and monogamous. Science experiment: Put on an episode of Friends and play the songs "All For You," "Roll to Me," and "Runaround" back to back. Attempt to sing one without inadvertently singing the others.
The Dave side is... it's Dave. You've been near a college before, right? While I have you here, have you ever listened to the part of that song where he says "and I come into you" without feeling like a giggly thirteen-year-old boy?
Euro-influenced kid-pop Representative cases: The Spice Girls, the Backstreet Boys, any group with five Aryan teenagers wearing CG body armor. Random, enjoyable single: I plead the fifth.
I am on the record as blaming Europe for boy bands as we know them, so I can't exactly back off that here. I'll go pretty far past what some might consider dignified for a great chorus hook, but the production style and the vocal affect of these bands never did it for me. (As Max Martin-svengali'd tracks go, I much prefer "My Life Would Suck Without You" to any of the Backstreet Boys singles.)
That said: They existed and it is my duty to record that. I'll let an RFT Music reader more open to the material than I am go further.
Summer Jam Band Representative cases: Smash Mouth, Sugar Ray Random, enjoyable single: I'm not sure if the one I'm thinking of is "Every Morning" or "Someday."
At the very end of the nineties, for a few sun-drenched years, "Songs with a kitschy beach party in the video, probably" inexplicably became a genre of pop music. I'm not complaining about this, but it happened, and Smash Mouth and Sugar Ray are the class of the group.
If I had to guess, I'd wager that in the distant past this species broke off and developed independently from the rest of the third-wave ska-punk bands (not pictured) and ended up, in a musical case of the Galapogos Effect, evolving a bunch of weird, purpose-made appendages, like the acoustic-guitar-with-a-DJ-effect-on-it and the rawk organ and the checked bucket hat.
Presumably the island where they were marooned had a bunch of tiki torches on it.
Shiny Crossover R&B Representative cases: TLC Random, enjoyable single: Mariah Carey - "Heartbreaker";
The shiny Crossover R&B guys--Boyz II Men et al--deserve a field worker who can truly enjoy Color Me Badd; unfortunately, that isn't me. What I like about the shiny crossover R&B girls and girl groups is that TLC's album art offers a concise summary of their two distinct classes: the early-90s-urban-chic model, in which our protagonists probably own a formal pair of rollerblades, for special occasions, and the late-90s-greasy-futurism model, in which our protagonists probably own multiple AIBOs and a DIVX copy of The Matrix.
Don't get me wrong, I'm a fan of both styles. I only picked "Heartbreaker" as the random enjoyable single because it features a woman wearing a bucket hat and a different woman wearing an unfastened pair of overalls in the first 25 seconds, and someone out there has probably been looking his entire life, without realizing it, for something exactly that sexy.
Oh, and the cartoon Jay-Z. There's also a Jay-Z cartoon in it.