Oops! He Hit Again: Ian’s Polarizing Freestyle Is Somehow Keeping XXL on Life Support
Over the last few years, XXL’s Freshman freestyles have felt more like contract obligations than cultural checkpoints. Artists show up, rap like they’re reading off the notes app, and vanish from the feed before anyone can pretend to care. Whatever magic the format once had — whether it was 21 Savage mumbling about running out of soda, or Lil Uzi Vert bouncing like a possessed pogo stick — it’s mostly been absent.
But Ian’s off-kilter 2025 freestyle, against all odds, brought the weird back.
Not the kind of weird that signals a misunderstood genius (not yet, anyway), but the kind that sticks.
A now-viral preview of the freestyle didn’t arrive with fanfare. It wasn’t hailed as a breakout. It wasn’t serious. It was clowned. Ian strings together a trio of bars that don’t rhyme, barely scan, and sound like they were assembled from the bottom of a bot-flooded Twitter thread:
“Damn, I'm on my Britney shit, oops, I hit again (Mmm)
Damn, I'm on my DJ Khaled shit, we the best (Mmm)
Damn, we rollin' hella deep, I feel like Adele (Mmm)”
Almost instantly, people treated it like performance art by accident. TikToks flooded in. People lip-synced the clip like it was Rebecca Black’s “Friday” all over again. Comments ranged from confused to gleefully cruel. And yet, everyone kept watching it. No one could escape.
This wasn’t just another freestyle preview. It was the moment of the rollout. And in a year when XXL felt dangerously close to falling into total irrelevance, Ian gave it a pulse.
By the time the full freestyle dropped, the punchline had started turning into a punchdrunk groove. Ian wasn’t trying to prove he could out-rap his peers — he was building something looser, more slippery. A mood, not a mission statement. The verse unravels like a fried group chat — half-thoughts, cultural references, red-eyed wisdom, and a few jokes too specific to be made up:
“Damn, I got this dyin' bitch, she just wanna be my friend (Mmm)
Damn, you’d think Flo Rida here, it’s going down for real (Mmm)
Damn, I’m a lil’ too high for this, Jesus, take the wheel (Mmm)”
The “mmm”s that punctuate each bar — offered by the other freshmen snapping behind him — sound like ad-libs, but they also feel like commentary. They echo the beat of a joke you’re not quite in on, or a vibe that’s still being constructed. It's hard not to hear an echo of “Hmmm” by HotHeadz, the mid-2010s viral video-turned-song that turned absurdity into rhythm. Ian’s verse operates in that same space: somewhere between music, comedy, and freestyle. It shouldn’t work, and yet it does, because Ian doesn’t seem to care.
There’s something strangely refreshing about watching a rapper who doesn’t pretend to have it all figured out. Ian floats through the verse like someone reading headlines off a phone he dropped in a bong, making sharp turns into earnestness before immediately crashing back into absurdity. One second he’s quoting 50 Cent, the next he’s channeling Nelly, then he’s demanding fellatio somewhere in the T-Mobile metaverse. The whole thing feels improvised in spirit if not in form, and that spontaneity is the point.
It’s not that the freestyle is technically strong. It’s not. And it doesn’t care to be. What it is, though, is memorable, which is something almost none of the other freestyles from this or recent classes can claim. Ian walked into a nearly dead tradition and turned it into a meme people actually liked. Not in a "this is funny because it’s bad" kind of way, but in that strange, irreversible way internet culture turns ridicule into affection.
Call it goofy. Call it unserious. But Ian conjured the only “Freshman Freestyle” moment this year that people didn’t scroll past. And for XXL — which has been trying to recapture lightning in a bottle for the better part of a decade — that’s more than a win. It’s a reboot.