Tyler, the Creator has had one of the most colorful and thrilling trajectories in hip hop. Tyler Okonma’s journey from angry, prodigious teenager to oddball creative and multi-hyphenate has been something to witness, to say nothing of the vital music he released along the way.

As a kid growing up in California, Tyler was musically inclined: He taught himself to play the piano and spent many hours buried in the liner notes of albums he loved. In 2007, he co-founded the collective Odd Future. The trail he would help blaze as their de facto leader was bright and—as the current careers of alumni Frank Ocean, Earl Sweatshirt and The Internet show—utterly necessary for the health of rap, R&B, funk and pop music today.

It was polarizing, of course. Thanks to their penchant for slinging homophobic slurs and indulging violent, sexual fantasies that often victimized women and other marginalized groups, Odd Future gained a reputation as an immoral force, though some also regarded them as misguided youths who prized shock value above taste and decency. And they suffered tangible repercussions: Feminist groups campaigned against them, and in 2015 Tyler was banned from the United Kingdom, its border force citing offensive song lyrics from his albums Bastard and Goblin.

Between 2015 and 2016, Odd Future dissolved, its members’ solo careers developing in varied, successful directions. Yesterday, Tyler released IGOR, his sixth studio album. To mark the occasion, we’ve narrowed down a list of five essential tracks from the rapper’s solo career. Dive in.

1“Bastard”

Many have heard Tyler’s early work, but they didn’t necessarily listen, even when he gave them songs like “Bastard.” On the bare-bones opening track of his 2009 debut album (or mixtape, depending who you ask), Tyler uses a classic storytelling frame of a therapy session to show people who he is, in all his multitudes.

He revels in the public’s fear-mongering perceptions—“N***a, I’m Satan’s son”—and mixes risible self-deprecation with knowing barbs: “I’m tall, dark, skinny, my ears are big as fuck / Drunk white girls the only way I’ll get my dick sucked.” On “Bastard,” Tyler blows his origin story up to mythical proportions. He’s larger than life, and yet, the shadow of his absent father still looms over him.

2“Yonkers”

Three words: Tyler. Cockroach. Noose. Put them together and you have the notorious music video for “Yonkers,” which firmly established the rapper’s reputation as an enfant terrible you couldn’t tear your eyes away from.

Of course, the song itself went a long way to turning Tyler into the pearl-clutching American parent’s worst nightmare. As the lead single of Goblin, the 2011 album released on the veritable British label XL Recordings, “Yonkers” had the reach that Bastard and Odd Future’s mixtapes didn’t. Over a sinister, RZA-aping beat that was apparently made in less than ten minutes, Tyler threatened the media, slung homophobic slurs and misogynistic tropes, and continued the Eminem-esque tradition of wishing violence upon pop stars. Potent and unapologetic, “Yonkers” is definitely one of the most pivotal songs of the Tyler canon.

3“Rusty” featuring Domo Genesis, Earl Sweatshirt

“Rusty” comes late on Wolf, but it’s worth the wait. Critics praised the 2013 album, many of them describing the project as a milestone in maturity for Tyler. That’s nowhere more obvious than on this track. Supported by his Odd Future compatriots Domo Genesis and Earl Sweatshirt, Tyler launches into a withering—but not insensible—critique of a public determined to misunderstand him. He makes telling observations (“Saying I hate gays even though Frank is on ten of my songs”) and argues that he’s a compassionate, not corrupting, influence: “Look at the kid who had the 9 and tried to blow out his mind / But talk is money, I said ‘Hi,’ I guess I bought him some time.”

As far as rappity-rapping goes, it’s impossible to dispute the top-notch performances on “Rusty,” whether the bars come from Tyler (“In a world where kids my age are popping Mollies with leather, sitting on Tumblr, never outside or enjoying the weather”) or Earl (“Malt liquor filling me up, and all us not giving no fucks and all of them sensitive chumps in awe when that pistol erupts”). Put that together with the clarity of mind and message Tyler exhibits, and it’s clear that “Rusty” is not only a vivid portrait of the rapper in 2013, but also one of the best songs of his career.

4“Smuckers” featuring Kanye West, Lil Wayne

Though created in 2011—initially for Jay-Z and Kanye West, no less—“Smuckers” was the last song Tyler finished for Cherry Bomb. Though critics have called the 2015 album one of Tyler’s more unfocused releases, “Smuckers” is an unquestionable gem. It’s a meeting of rap greats, with West, Lil Wayne and Tyler spurring each other on to bring their A game.

On “Smuckers,” Tyler experienced the rare and sublime thrill that is inspiring your own influences. “I played it for Ye at his house literally four days before the album was due. He was like, ‘Ok, I got to step my bars up. Y’all n***as is spitting,’” Tyler enthused to Billboard at the time. “It was such a sick thing to know that me and Wayne had to put Ye back on his feet. Like, what the fuck? I’m 24 years old. What am I going to look forward to at 30?”

5“See You Again” featuring Kali Uchis

A departure from the more jagged, experimental facets of his music on Cherry Bomb, 2017’s Flower Boy was the point where Tyler (excuse the pun) truly bloomed. Employing lush, mellow soundscapes and more live instrumentation than on his previous albums, the Golf le Fleur tastemaker seized the opportunity to become his friendliest—and most vulnerable—self. (“Next line, I’ll have ’em like whoa / I’ve been kissing white boys since 2004,” he raps on “I Ain’t Got Time!”)

One standout among many on Flower Boy is the sultry “See You Again.” On this heartfelt ode to love, Tyler and regular collaborator Kali Uchis swap lyrics on budding infatuation and an evergreen romance. The loved-up track has had quite the history, having started out as a reference track for Zayn. According to Tyler, the song eventually ended up on the album after the former One Directioner flaked on him. And man, are we glad he did.

Stream IGOR here.