Last year, Tyler, the Creator, real name Tyler Gregory Okonma, aka Ace, aka Tron Cat, aka Sam, Dr TC and Wolf Haley, released IGOR, his sixth full-length album and it was nothing short of a damn masterpiece.

It’s now more than a decade since Tyler emerged as the face of Odd Future Wolf Gang Kill Them All, the controversial Californian skater crew/rap collective that would provide a platform for the successes of Earl Sweatshirt, The Internet, Frank Ocean and more. The group’s ringleader has since graduated from rapping about “fucking faggots” and being banned from entering the UK to writing a soundtrack for a children’s Christmas film, helming a global fashion brand, running a music festival, producing a fucking scented candle and becoming one of the biggest rappers in the world. Here’s how he got from then to now, via 25 of the very best Tyler, the Creator songs.

25. “See You Again”

He’s a sweetheart really. “See You Again” is reportedly Tyler’s favorite song from 2017’s Flower Boy, and possibly the finest pop track he’s ever written. It’s a love song about seeing your ideal heartthrob every time you close your eyes, which is a bit like Kali Uchis’ chorus — listen now and it will be wandering around your mind all day. We have Zayn Malik’s poor punctuality to thank for it too: in another world it could have been him singing these lines. And nobody wanted that.

24. “I Am the Grinch”

In many ways, Tyler writing songs for The Grinch makes a lot of sense. I mean, in many ways it makes no sense, obviously, but aside from the fact that he’s a polemic rapper soundtracking a children’s film, he is essentially a big kid, obsessed with colors, waffles and Rugrats. Also, just like the hairy green tormentor of Whoville, Tyler seems scary and mean from afar, but is all soft and cuddly up close. Fingers crossed Earl Sweat does the soundtrack for the next Cat in the Hat reboot.

23. “911 / Mr. Lonely”

There would be nowhere near the same hype around IGOR if it hadn't been for Flower Boy. To date it’s Tyler’s magnum opus, a work of complex, considered brilliance. Typical of that complexity is the double-edged “911 / Mr. Lonely”, a breezy, carefree slowjam that could work as on-hold music were it not for the lyrical references to suicide and chronic loneliness throughout.

22. $ilkMoney — “NAGA” ft. Tyler, the Creator

Despite only releasing about eight songs in the space of four years, Divine Council are still the hottest rap group to emerge since Odd Future. So Tyler’s collaboration with the Council’s $ilkMoney makes perfect sense: he’s on production here, teasing rumbling synth lines that recall 2011’s Goblin. His verse ain’t bad either.

21. “Bastard”

The first track on Tyler’s first mixtape, “Bastard” announced a new rapper on the scene with an opening skit taking shots at any blogger who hadn't yet taken notice of him. Across nine verses (and no choruses) Tyler weaves between references to Heelys and Disney movies to his absentee father and strangling imaginary girlfriends. It’s also the introduction of Dr TC, the fictional psychiatrist with whom Tyler discusses his problems throughout Bastard, Goblin and 2013’s Wolf.

20. Ace – “Fin”

Looking back on the very first Odd Future Tape now prompts many writers to describe a teenage Tyler using terms like “remarkably fully formed.” That’s fair enough: he produced the whole thing while rapping under an array of different aliases. On “Fin” he goes by Ace, reeling off a list of acknowledgements to all his biggest influences, including his nearest and dearest, fashion brands like Supreme and Billionaire Boys Club and albums like Sade’s Love Deluxe and Radiohead’s Kid A, as well as some slightly more egregious choices like Hitler, Stalin and “all the porn in the world.”

19. EarlWolf – “Orange Juice”

Using the sumptuous piano instrumental from Gucci Mane’s “Lemonade,” “Orange Juice” showed why Tyler and Earl were many early Odd Future fans’ two faves — and also why they weren’t such a hit with rap fans’ moms. The two channel OJ Simpson (geddit? OJ?) with bars about nuns, erections and duck-taping mother geese, but Tyler takes the gong with that line about Jack and Jill.

18. “Rusty”

Speaking of mums: Tyler, Earl and Domo Genesis’s performance of “Rusty” on Letterman in 2013 epitomized the Odd Future explosion. They were rude (check all the censored swearwords); they had their own look; they could rap better than anyone else around; and the mainstream media had absolutely no idea what to make of them. Even more excruciating (and hilarious) than this is their appearance on BBC’s Newsnight.

17. “Garbage”

Unbeknownst to some, it’s actually possible to play Grand Theft Auto without turning into a serial car thief in real life. Similarly, listening to Tyler, the Creator lyrics about murdering white girls is not necessarily an endorsement of the crime in question. Anyway, something about “Garbage” makes it a fitting choice for the GTA V soundtrack.

16. “Seven”

It’s easy to imagine indie jazz-hoppers BadBadNotGood getting on well with the Odd Future crew. Aside from a shared fondness for Supreme, bucket hats and MF DOOM, the two acts first emerged brimming with a similar youthful talent at odds with the rest of contemporary music. Tyler’s attention was drawn to the Canadian band after they uploaded a cover of “Orange Juice” to YouTube; not long afterwards they were collaborating, as on this version of Bastard cut “Seven.” “I didn’t mean to offend anyone… alright, I’m lying,” Tyler grins in one lyric.

15. Odd Future – “White”

Frank Ocean used to say he looked up to Tyler despite being three years older than him. It’s easy to hear why: on tracks like “White,” Tyler’s creamy production oozes around Frank’s voice like custard round a sticky toffee pudding, unlocking unfathomable new flavors in the singer’s voice. This track, taken from 2012’s The OF Tape Vol. 2, was a glimpse into the future for both artists, nodding towards both Flower Boy and the imminent Channel Orange. It’s a highlight in both their discographies.

14. Earl Sweatshirt – “Sasquatch” ft. Tyler, the Creator

Let’s just say this now: Earl’s album Doris, released in August 2013, is better than Wolf, which came out four months earlier. BUT: its best moment is “Sasquatch,” and that’s largely thanks to Tyler, whose verse sees him fantasize about driving to a One Direction gig to see how many fans he can kidnap. It also includes a James and the Giant Peach reference, a mention of Chris Brown and Rihanna (“Oh fuck I went there!”) and the line “we running shit like the dingleberries on four cheetahs.”

13. “Awkward”

The best thing about Wolf, other than the dreamy Frank Ocean choruses, all three versions of the artwork and the interplaying psychodrama between the two sides of Tyler’s personality, is that most of the instrumentals sound like they’ve been sampled from hotel lobbies in the 1980s. Walking the tightrope between easy-listening ambience and tales of getting caught masturbating just about sums up the Tyler experience. “Awkward” is a prime example.

12. WANG$AP – “Potato Salad”

Hopefully, the more we refer to Tyler and A$AP Rocky as “WANG$AP,” the more likely it is that they'll record an album together. Such a record, though still a long way off in a half-imagined future, would represent a beacon of hope for rap fans amid all that mumbling and rambling (“mumble-rapping?!”) that’s out there at the moment.

11. “Blow”

“Blow,” released on Bastard when Tyler was 19, is told from the perspective of Ted Bundy, the serial killer found guilty of murdering at least 30 people in the 1970s. Lines like “you call this shit rape but I think that rape's fun” eventually led to Tyler being banned from touring in certain countries, including the UK, with Theresa May — then home secretary — believing that his songs might “provoke terrorist acts.” Though Tyler has since tidied up his lyrics, his early work remains vital, testament to a young rapper who thrived on diving deep into social taboos.

10. Pusha-T – “Trouble On My Mind” ft. Tyler, the Creator

OK, Push goes hard on this track. The Neptunes’ production is banging. And the chorus is fire. But Tyler destroys. Following one of his most iconic lines (“I wanna fuck the world but not a fan of using condoms”) he switches between flows mid-line like only he can, spitting bars about wet willies, Free Willy and Will Smith. It’s among his best ever verses.

9. “Find Your Wings”

Cherry Bomb, Flower Boy’s predecessor, is a weird album. From songs about fancying underage girls to recording at Hans Zimmer’s studio, it’s the sharpest left turn in Tyler’s oeuvre. Its best moment is the soul train lullaby “Find Your Wings,” with none other than Roy Ayers lending his sweet voice to the track. Considering the soul direction Tyler took next, this now sounds like a portent of things to come, not least in its fuzzy, '70s video.

8. “WHAT THE FUCK RIGHT NOW”

Convertible car, top down, speakers pumping, dollar signs on the wheels and a license plate that says ‘PLAYUH.’ Listening to “WHAT THE FUCK RIGHT NOW” feels like driving one of those.

7. “She” ft. Frank Ocean

Maybe the best Tyler-Frank combination to date. It starts like a classic Frank love scene, the beloved crooner using verse one to paint a lovely picture of a bedroom romance. But before the first chorus there’s Tyler at the window in full stalker-mode, and by verse three he’s dragging bodies into forests. Call it horrorcore hip-hop, exploitation rap or necrophiliac funk, there’s nobody better at making us grin, gasp and grimace in the same song.

6. “OKRA”

Described by Tyler as a ‘throwaway’ track that he fired off while on tour last year, “OKRA” is all guttural bass and quickfire braggadocio rap, the sort that makes subwoofers tremble. It typifies Tyler’s penchant for deep club tools, occupying the sorts of frequencies most often associated with South London dubstep circa 2004. Which, as we all know, is when Tyler first started kissing white boys…

5. “I Ain’t Got Time!”

Tyler sounds so much more mature on Flower Boy, outing himself as gay and using key changes and devil’s tritones like a composer rather than a typical hip-hop producer – just kidding. Tyler’s good whether he’s gay, straight, acting like a grownup or fooling around like the class clown. He’s a ‘composer’ whether he’s making classical music or hip-hop, and complexity is not superior to simplicity. “I Ain’t Got Time!” may feature that line about snogging white boys since the mid-noughties, but it’s designed to provoke riots at house parties, not chin-stroking thinkpieces.

4. “Radicals"

Random disclaimer: “Hey, don’t do anything that I say in this song, OK? It’s fucking fiction. If anything happens, don’t fucking blame me, white America.” So says Tyler at the start of “Radicals,” an OG OF banger about nihilistic fuck-yous-all-round. You got that, everyone? Don’t get upset by the extreme content. Don’t blame rap music for society’s problems. Don’t complain to the BBC. Most of the time it’s just a bit of fun. Fuck Bill O’Reilly.

3. Odd Future – “Oldie”

Odd Future were over by 2015, but their impact on hip-hop, fashion, and internet culture is greater than just about any other act this decade. “Oldie,” which remains the definitive OF posse cut, shows the group exactly as they were at the time: a group of teenagers trying to make each other laugh. While Tyler is center-stage, rapping first and last, verses from Earl and Mike G are at least as good. Also, hold tight for Frank hanging around in the video like he’s been dragged to a birthday party by his younger brother.

2. “Garden Shed”

Is this the moment Tyler came out as gay, offering an unexpected twist in the tale of a rapper once labeled as violently homophobic? Or is it yet another ploy from rap’s most devious prankster, a smirking middle finger to the critics who once lampooned him? In truth, we don’t know. But it’s everything you could have ever wanted from a Tyler track: its luscious chords feel almost weightless, as though recorded in a studio with zero gravity, topped only by a verse replete with word play, laser-speed rhymes and a healthy dose of vintage, jaw-dropping, OFWGKTA shock factor.

1. “Yonkers”

The thing about Tyler — bless him — is he often distances himself from his old music, talking about Goblin and the like as though he’s long since moved on. And that’s great: we don’t want him to dwell on the past, to stop coming up with crazy new shit. But “Yonkers” sent shockwaves through the music industry when it dropped, boasting the toughest beat and the best opening line of any rap song in a decade. And he eats a cockroach in the video, for fuck's sake. Enough said.