Madonna wore a cone bra in 1990 and basically broke the internet before the internet existed. Olivia Rodrigo wore a corset and cried on stage at the Grammys in 2024 and did roughly the same thing. Different decades, same trick: take something raw, make it theatrical, and watch everyone lose their minds. That’s pop music. It never actually changes, it just gets new faces.

Okay But Who’s Actually Running Things Right Now

Let’s not pretend this is complicated. Right now, in this exact moment, it’s Olivia Rodrigo, Chappell Roan, and Sabrina Carpenter running the show, with Beyonce and Taylor Swift hovering above like the two moons of pop culture that never quite set. And honestly? I think that’s a good thing. For years we had this weird stretch where pop felt kind of… corporate. Polished to death. Nobody was messy on purpose.

Rodrigo changed that. “Drivers License” came out in January 2021 and I remember exactly where I was when I heard it – stuck in traffic, ironically – and thinking, oh, this girl is going to be a problem for every other pop star for the next decade. She was 17. SEVENTEEN. And she wrote a song so specific, so devastatingly detailed (the yellow light, the good four seasons, come on) that it didn’t feel manufactured at all. It felt like reading someone’s diary that they forgot to lock.

The Sour Effect

Her album “Sour” basically kicked off this whole era of pop girls being allowed to be angry, awkward, and a little unhinged in public. Before that, a lot of mainstream pop wanted you polished and grateful. Rodrigo made bitterness a genre. And then “Guts” doubled down on it in 2023 with tracks like “Vampire” and “Get Him Back!” that were funnier and meaner and somehow even more popular. Not gonna lie, I think “Guts” is the better album. Fight me.

Chappell Roan Came Out of Nowhere (Sort Of)

Here’s the thing about Chappell Roan – she didn’t come out of nowhere at all. She’d been grinding for years, got dropped by Atlantic Records in 2020, and then clawed her way back with “The Rise and Fall of a Midwest Princess” in 2023. It took almost a full year for that album to actually hit. That’s the part people forget. We love a good overnight success story but this wasn’t overnight, it was a slow burn that finally caught fire around summer 2024 when “Good Luck, Babe!” turned into the song you couldn’t escape at literally any bar, wedding, or grocery store.

“I’ve always known I was going to be a pop star, I just didn’t know when everyone else would figure it out too.” – something close to what Roan has said in interviews, and honestly, the confidence tracks

What’s interesting here is how theatrical she is. Drag-inspired makeup, over-the-top stage outfits, characters within characters. This isn’t new – Madonna did it, Gaga obviously did it, Kylie Minogue did it for decades in a slightly different lane – but Roan’s version feels queer and unapologetic in a way that mainstream pop kept at arm’s length for way too long. She’s not asking permission. That’s the difference.

So Where Does Madonna Fit Into All This?

Everywhere. That’s the honest answer. You cannot talk about reinvention in pop music without her, full stop. She’s been doing this since 1983 and she’s STILL doing it – the Celebration Tour in 2023 and 2024 proved that even at 65 (yes, 65) she can sell out arenas and make headlines just by existing loudly. People act shocked by this every single time and I genuinely don’t understand why. She’s Madonna. She invented the blueprint that basically everyone above is following, whether they admit it or not.

Think about it. Constant reinvention? Madonna. Using controversy as marketing? Madonna. Fashion as a weapon, not an accessory? Madonna, obviously. Even the confessional, brutally personal songwriting that Rodrigo gets praised for – Madonna was doing versions of that on “Like a Prayer” back in 1989, and people were burning her in effigy for it (literally, the Vatican condemned that video). Nobody’s burning anyone in effigy over “Drivers License.” Times change. The DNA doesn’t.

A Quick Reality Check

I know some people will read this and think I’m overstating the connection. Maybe I am, a little. These artists didn’t sit down and study Madonna’s playbook page by page. But culture works in echoes, not straight lines. Sabrina Carpenter’s whole “short ‘n sweet” era, with the winking innuendo and the theatrical stage banter mocking her exes by name during “Please Please Please” – that’s got Madonna’s fingerprints on it whether Carpenter meant it that way or not.

The Part Nobody Wants to Say Out Loud

Here’s my actual hot take, and I stand by it: pop music right now is better than it’s been in probably fifteen years. There, I said it. For a long stretch in the 2010s it felt like everything was optimized within an inch of its life – written by committee, tested on focus groups, sanded down until there were no edges left. Songs that were fine. Just… fine.

What changed? I think TikTok gets some credit here, even though I hate giving TikTok credit for anything cultural because it usually ruins things too. But it flattened the gatekeeping. A song can blow up because it’s genuinely good and weird and specific, not because a label spent millions pushing it onto radio playlists. Rodrigo’s early stuff spread that way. Roan’s did too, eventually. That’s given artists room to be stranger, more personal, less focus-grouped.

And the older icons – Madonna, sure, but also Cher, also Dolly Parton in her own lane – they benefit from this too, weirdly. There’s a whole generation of younger fans discovering them through clips and remixes and going “wait, this woman was doing THIS in 1985?” It’s created this strange loop where the past and present are basically talking to each other in real time. I don’t think that’s happened quite like this before, not at this speed anyway.

What This Actually Means

If I had to guess where this goes next, I’d say we’re heading toward even more blurring between eras. Expect more collabs across generations (a Madonna and Rodrigo team-up wouldn’t shock me at all, honestly it feels almost inevitable at this point). Expect the theatrical, slightly chaotic, unapologetically feminine pop star to keep winning over the buttoned-up, market-tested version. And expect people my age to keep being surprised every time a 20-something writes a song that sounds like it was ripped out of a diary from 1986, because apparently we forget that feelings are feelings no matter what decade you’re stuck in.

The real throughline isn’t the sound, or the outfits, or even the drama, though God knows there’s plenty of that to go around. It’s honesty dressed up as spectacle. Madonna figured that out first. Everyone since has just been remixing it. And I, for one, am completely fine watching that cycle repeat for another forty years.