The Best New Artist Grammy award has a fascinating and bizarre history. The Beatles won it. Bob Newhart won it. Bon Iver won it. Bette Midler won it. Christopher Cross won it. Milli Vanilli won it and then had to give it back when the world found out that the two members of the group hadn’t sung a note on their album. (The 1990 award still stands vacant, which has to suck for the Indigo Girls, Soul II Soul, Neneh Cherry, and Tone Loc, the four artists who all got beat by the lip-syncing Germans.) Paula Cole won it, somehow defeating Fiona Apple and Erykah Badu and Puff Daddy. You know who hasn’t won the Best New Artist Grammy? Rappers. Rappers have not won that award. Digable Planets lost it to Toni Braxton. 50 Cent lost it to Evanescence. Kanye West lost it to Maroon 5. Drake lost it to Esperanza Spalding.

Before Sunday night, only three rap entities had ever taken home the award, and the extent to which all three are “rap entities” is very much debatable: Arrested Development, Lauryn Hill, and Macklemore and Ryan Lewis. That is not a great batting average. Of those three, Arrested Development and Macklemore/Lewis both followed up the albums that won them their Grammys with notorious flops. Hill — the most credible rap winner, even if she probably won the award more for her singing than for her rapping — still has yet to make a second studio album. If the Best New Artist award is supposed to recognize the people who will be dominating music for years to come, then the curse that famously often comes with Best New Artist applies more to rap than to pretty much any other genre of music.

Moreover, the three past winners represent, in one way or another, a Grammy voter’s idea of rap: sanitized, melodic, family-friendly, heavy on live instrumentation and social messaging. (And given that Macklemore beat Kendrick Lamar, who also checks most of those boxes, we might as well add “corny” to that list.) What, then, are we to learn from the fact that Chance The Rapper is our current reigning Best New Artist? If he’s the type of artist who a notoriously clueless institution like the Grammys can recognize, does that compromise him? Is Chance The Rapper corny now?

If Sunday night’s Grammys were a victory for the forces of white mediocrity, then Chance’s Best New Artist win was a rare bright spot, a rare non-genre-specific victory for a great black artist from a traditionally black musical tradition. Chance is the first person of color to win Best New Artist in six years. (Chance isn’t even remotely new, but the Grammys don’t care about that.) And he’s the first ever, in any category, to win for music that only existed in an online-streaming capacity. He won Best Rap Album for something he called a mixtape, and he thanked DJ Drama, from the podium, for helping to pioneer the field. As a performer, Chance has the rare ability to appear completely emotionally overwhelmed every time he hits a new career milestone — a sort of sincere version of the surprise face that Taylor Swift used to make every time she won an award. It’s hard to think about Chance’s win as anything other than an unalloyed, unambiguous Good Thing. But it also comes after a few months of exploding mainstream visibility. And is it going to be harder to get excited about Chance when he’s headlining huge festivals and hugging Ellen DeGeneres? When he’s a fully embedded part of the pop music establishment?

Keep in mind: Plenty of people already think Chance The Rapper is corny. Plenty of people have been thinking it for years. Plenty of people who now love Chance The Rapper had to get over the corniness threshold, to train themselves to love the yawpy ad-libs an the voice-cracks and the general hyperactive teenage energy. When Chance won Best New Artist and howled the word “God” in his acceptance speech about 32 times, I saw plenty of grumbling — We get it, dude, you believe in God — in my Twitter timeline. Someone even said that the music industry had figured out how to manufacture a marketable version of Christian-rap figurehead Lecrae. And that gets at another common complaint about Chance: that he’s an “industry plant,” a creature created by the music business, one who uses “independent” as a buzzword rather than as any kind of unifying philosophy. Those of us who love Chance, that line of thinking goes, have been somehow hoodwinked or manipulated into it. And there have been plenty of other perceived sins over the years: the overalls, the KitKat commercial, the constant references to Nickelodeon cartoons, the persistent smiling. Whether or not you love Chance, there is a strong possibility that he’s annoyed you once or twice.

And in light of his big Grammy night, Chance’s general wholesomeness takes on a new air. It’s one thing to be rapping about faith and family on Acid Rap, a mixtape that was very much a product of the Chicago after-school freestyle-cipher scene and one that was received, and understood, as such. But when parents and high-school principals across the nation know who Chance is, when that context drops away, Chance’s radical positivity looks somehow different. On his breakout single, “Juice,” Chance was smart enough to preemptively shout out Chief Keef, and a whole lot of the music press still held him up as the yin to Keef’s violent, nihilistic Chicago-rap yang. What happens when people who don’t follow rap music like that are suddenly doing the same thing with Chance, looking at him like he’s an antidote to an entire genre? An entire genre that Chance himself loves and respects and represents? It’s just weird. And it’s weirder still that Grammy capo Neil Portnow, in this interview, holds Chance up as evidence that there is nothing wrong with the way the Grammys handle race. None of it sits right.

Here’s the thing, though: Chance was always corny. It’s baked in. It’s a part of his appeal. Until very recently, this guy’s biggest track was a love song to his grandmother. He’s been playing around with gospel music since 10 Day, and he’s been cranking out weirdly euphoric, sunshine-embracing melodies for just as long. He’s never been even remotely dangerous, so it’s not like he’s selling out that side of himself. Coloring Book was, for my money, last year’s best album — rap or otherwise — because of the radical, world-encompassing joy it radiated. In an incredibly short period of time, Chance has become a master at conveying enthusiasm and uplift and transcendence while still acknowledging darkness and despair and poverty. There will always be context to his music because he will put it there. He will make sure that you can hear it.

If Chance has become a deeply marketable artist — a real threat to join rap’s rarefied Drake/Kanye West/Kendrick Lamar A-list tier — it’s because of his own wily charisma and his songwriting abilities, not because he’s an expert salesman. I mean, he is an expert salesman of himself, one who understands how to turn every televised performance into and event and every new mixtape into an expert display of curation. But that salesmanship feels almost incidental to his artistry. A year and a half ago, I watched Chance headline the Pitchfork Music Festival in his Chicago hometown, and it felt like every kid in that field that night knew every word to every mixtape track. That connection was organic and deeply felt, and it won’t go away now that people are tripping over themselves to throw trophies at Chance. He didn’t ride some wave to get to where he is, even if a wave of smart and open-hearted young Chicago rappers did follow. He brought the rap mainstream to him; he didn’t meet them halfway. That’s not easy.

As long as Chance never signs to a major label — and, at this point, why would he? — he’ll always have a built-in underdog narrative. He teamed up with Apple, of all possible conglomerates, to unveil the release of Coloring Book last year, but he still made sure the mixtape showed up on DatPiff at the exact same time. (If memory serves, Chance posted it to DatPiff from his own account; it wasn’t a case of a fan bootlegging it.) He’s got a tricky road to walk right now — reflecting the darker and more severe mood of the country while maintaining his broad popular appeal and his outsider context. But if anyone can pull that off, it’s Chance. After all, it’s not his fault the Grammys got something right for once. And a year or two from now, we’ll all be able to watch him lose Album Of The Year to Ed Sheeran or whoever, to get righteously angry all over again.

FURIOUS FIVE

1. Migos – “Dap Of Ranch”

Migos had a rough week. Their Rolling Stone profile revealed them to be deluded homophobes, something their blatantly publicist-generated apology could never dispel. And there’s also a moment in the story where Offset and/or Quavo appear to punch out a woman. They come off like, quite simply, bad people. But as we hear in this song, bad people can still rap euphorically about their own potato chip brand. And, I mean, I’m not made of stone.

2. Blac Youngsta – “Hip Hopper” (Feat. Lil Yachty)

“I do not fuck with no hip-hoppers” is a great way for Atlanta’s young insurgents to declare war on the Ebros on the world, especially when they rhyme it with “she sucked my dick in my flip-floppers.” Never go against the children of the world. The children will bury you.

3. Rick Ross – “Summer 17″

Suddenly, it feels like 2010 again. Someone needs to convince Ross to stop making silk-pillow rap, to always sound like he’s got something at stake. When he’s got fire in his eyes, he’s one of the greats.

4. Danny Brown & Paul White – “Lion’s Den”

As a rapper/producer pairing, Danny Brown and Paul White thrive on the noisy and chaotic and freaked-out. But for my money, “Accelerator” was too noisy and chaotic and freaked-out. I didn’t like listening to it. It made me nervous. This song, by contrast, eases into that head-blown feeling. There’s nothing pedestrian about it, but I can listen to it without my chest constricting.

Accelerator by Paul White ft Danny Brown

5. Avelino – “Energy” (Feat. Stormzy & Skepta)

I love how grime guys have managed to incorporate big EDM drops without sounding like they’re selling out. The hardcore-rave continuum remains strong.

IT WAS ALL GOOD JUST A WEEK AGO