Tyler the creator performing bucket hat striped shirt
Highsnobiety / Daniel Garcia

If you, like we did, enjoyed IGORTyler, the Creator’s recent fifth LP — while feeling a sensation of loss for the days when a Tyler song meant a serving of side-splitting raps: for three reasons, fear not.

Firstly, as Tyler himself pointed out on Twitter in response to a dissenting fan, his old music — the razor raps of Bastard, Odd Future’s raucous circle jerking — continues to exist. Thanks to the internet, it’s just a few clicks from your ears as you read this very article.

Secondly, one should not implore an artist to stay in the same place. New ideas, upheaval, and innovation are what we need to keep music interesting. Complaining at Tyler for not rapping enough on IGOR is like complaining about Kanye not rapping enough on 808s & Heartbreak, or complaining about The Beatles not playing enough blues on Rubber Soul.

Thirdly — and best of all — he just gave us a rap, a freestyle in fact, on Funkmaster Flex’s Hot 97 radio show. Making his host fidget with discomfort, T laid down an impromptu verse referencing his erstwhile imprisoned buddy A$AP Rocky, R. Kelly’s wet dreams and looking in phone books for hot butt sex. We’ll come to what made his Flex Freestyle so sick, but first, here’s a run-through of Tyler’s history in subverting the conventions of freestyling.

“Home Alone Freestyle” (2008)

In simpler times when he was but a wee lad, Tyler was primarily interested in skating, ice cream and, like, colors and shit. More than a decade later, he hasn’t actually changed all that much, as evidenced by this clip of a teenage T spitting into a camera while at his mom’s new house in Sacramento. Announcing himself with an “umm” — which has become something of a trademark — and a greeting only he could have come up with, he lays down some babyfaced bars over an instrumental he later gave to Hodgy Beats for the Dena Tape track “Sorry.” It’s a snapshot of the boy’s formative years, including zeitgeisty references to Obama, Osama Bin Laden and MySpace — all off the top of his noggin.

“SBTV Freestyle” (2011)

SBTV, or SmokeyBarz, is a British YouTube channel founded in 2006 by a young Jamal Edwards, who here takes Tyler and Hodgy into the arse-end of the UK (“we just found a crack pipe,” says Tyler at one point) for an exhibition of the two ways to define “freestyle.” Spitting a capella, Hodgy fires off a cold verse about getting high in Ohio and his step-father’s cardigan, with nothing prepared.

But to say that makes it a true freestyle only adheres to one interpretation of the term: as former Juice Crew MC Big Daddy Kane explains, “freestyle” originally meant a verse about nothing in particular, i.e. a rap that is free of style. Under that definition, Tyler’s written verse is a freestyle too. Plus, when it opens with a line about his mom walking in on him jacking off to Hanna Montana with a banana peel, who cares?

“Sway” (2013)

By 2013, Tyler was a superstar. Though still only 21, he’d already self-produced a mixtape, a debut album, and three Odd Future full-lengths, pissed off numerous angry parents and eaten a cockroach. Rocking up to the coveted US radio show ‘Sway in the Morning’ on the eve of new album Wolf, he was notorious. After a hilariously polite introduction to every member of the studio crew, Tyler informs host Sway Calloway that his upcoming record is “the worst shit I could possibly make. The album fucking sucks.”

His subsequent cipher shows Tyler in full cantankerous mode, parodying that this-decade brand of squeaky-voiced New York gangster MC with bars about hot dogs and AKs the size of a minivan. He repeats the trick in the equally funny a capella sequel, insisting “my name is my NAME” in the voice of a gimmicky SoundCloud rapper who’s listened to Clipse’s Hell Hath No Fury once. Is this a man who sees any public appearance as an opportunity for performance art? Or a grownup boy who can’t do anything without making a mockery of it for his own amusement? Either way, it’s jokes.

“Camp Flog Gnaw Freestyle” (2016)

Keep your eyes peeled around the 1:40 mark in this clip from 2016’s Camp Flog Gnaw Festival, the music gathering Tyler started with the OG OFWGKTA crew earlier in the decade. Midway through Wolf-track “Rusty” with Earl Sweatshirt and Domo Genesis, Tyler looks skyward and outstretches his arms in a dumfounded posture. “And I forgot my verse, fuck it we ain’t trippin’,” is his next line, introducing 16 bars you’d be proud of if you’d written them in a month but which Tyler spits with seamless swagger straight off the domepiece. Also, is that Erykah Badu backstage in the hat?

“Funk Flex Freestyle” (2019)

Right, kids, in case you don’t know, Funkmaster Flex was the first ever host of a hip-hop radio show on Hot 97, a slot that went on to become one of the foundational pillars of rap culture throughout the ’90s. Also rapping himself, as well as DJing and producing for a huge number of big name MCs (including Tupac and Biggie, on the same track), he is — still — kind of a big deal. He’s also a member of hip-hop’s old guard and a self-confessed skeptic of the Odd Future explosion.

By contrast, 28-year-old Tyler is as fresh-faced as he’s ever been, less interested in Rolies and bitches than flowers and sweet men, and currently the funniest rapper in the game. Whatever you do, don’t skip to the end: the interview is a fascinating meeting of minds in which Flex opens up about the time Earl said JAY-Z’s latest album was overrated (most likely referring to Magna Carta Holy Grail — which was kinda shit, wasn’t it?) and Tyler reveals he’s never listened to early hip-hop classics by Boogie Down Productions and Eric B & Rakim.

Speaking about another of his favorite artists, Flex then tells Tyler how former EPMD rapper Erick Sermon used to make regular visits to a friend in jail, asking about the latest slang words so he could slip them into his upcoming verses. This impresses Tyler, himself an MC who’s known to fit to-the-minute nods to social media into his raps, such as his mention of the “cancel couch” trying to dig out homophobic tweets from his timeline, in this very freestyle no less. He then drops lines about getting it on with Flex, making his host squirm and exposing hip-hop’s generation gap with the kind of irreverence no other rapper has shown in years.

For more about Tyler, The Creator, watch the video below.

Words by Sam Davies