Still poking around the Billboard Year-End charts to see how things have changed since the '90s. Society had already entered the cocooning phase, but it was only several years into it, rather than 20-odd years into it.
Also, change doesn't always affect every individual -- it's not as though every pop star of the '90s was a watered-down version of their counterpart from the '80s. Some individuals still showed signs of the '80s climate, they were just fewer and fewer in number each year.
Looking over the charts from '93-'95, you can still see a remnant of the outgoing and socially connected world of the '80s -- the clingy girlfriend song. Torch songs wouldn't be popular if young people didn't really care that much about connecting, whether due to mousiness and celibacy or glibness and promiscuity.
Some examples, whether traditionally sentimental or with a then-contempo indie / alternative dressing. I wasn't very into rap or R&B, so won't remember any examples from that growing domain of pop music.
"I Will Always Love You" by Whitney Houston
"I'll Never Get Over You (Getting Over Me)" by Expose
"Again" by Janet Jackson
"Stay (I Missed You)" by Lisa Loeb
"Linger" by the Cranberries
"Take a Bow" by Madonna
"You Oughta Know" by Alanis Morissette
Musically these aren't as catchy as the clingy girlfriend songs from the New Wave heyday like "Goodbye To You," "Only the Lonely," and "Johnny Are You Queer". I'm just talking about the tone of the lyrics revealing that there was still a residual sign of people wanting to connect with each other, and feeling loss if that bond were broken.
Twenty years further into the cocooning phase, female singers don't even talk about the aftermath of a relationship, since everyone in the audience is too socially awkward and frightened to "reach out" in the first place.
The most popular songs all convey a profound fear and dread about the very beginning when you're only asking someone out on a date, getting to know them, and so on. Merely dating somebody has become this looming apocalyptic scenario, where if the other person rejects you outright or it fizzles before anything happens, you'd be so mortified that the world might as well explode.
It sounds like the singer is a 6th-grader blasting "Carmina Burana" in her room to pump herself up to ask her girl friend if she'll ask her crush if he likes her back. "Dark Horse," "Boom Clap," "Blank Space," etc etc etc. It's all middle school apocalypse music.
Where the torch song showed a level of maturity that allowed a relationship to fully run its course, and a desire to trust others and keep them close even afterward, the emo anthems of today show how stunted the audience is in the stage of development when you're still too awkward to open up to the opposite sex, as well as a distrust of others (MUST NOT EVER BE REJECTED), including your peers, who you feel like keeping a safe distance from, except to scratch the occasional lust itch (or maybe not even then).
Keep your ears open for signs that the cocooning phase is winding down. By the latter half of the '50s, when folks were leaving their Midcentury drive-in cocoons, they were in the mood for a sincere torch song like "Making Believe" by Kitty Wells (#2 on the Country charts). I prefer the version from further into the outgoing phase, performed more tenderly by Emmylou Harris: