Andrew Unterberger: So let’s start off with album of the year. Recent history suggests it’ll go to the biggest pop act — Taylor Swift, Adele and Bruno Mars were the last three winners — but the artists you’d expect to follow in that sequence in 2019 — Ariana Grande, Justin Timberlake, Swift again — weren’t even nominated. There’s Drake, of course, but his history of Grammy no-shows will likely rub too many voters the wrong way. The category has never been kind to Cardi B’s brand of relatively traditional hip-hop. And Post Malone… Well, let’s come back to him later.
Am I crazy for thinking that Brandi Carlile’s By the Way, I Forgive You has a real shot? She has major industry support and respect, even from President Obama; her album was unanimously acclaimed; and with the expanded pool of nominees, a left-of-center act might have a better shot of standing out.
Stereo Williams: I don’t think Carlile is entirely a stretch for album of the year. H.E.R. could be a somewhat unexpected win: Everyone seems fascinated by her rise from child talent to mysterious newcomer to mainstream star. Black Panther makes a strong case: A hip-hop album taking the night’s biggest honor is well overdue — it has been 15 years since OutKast won it.
But I really think Janelle Monáe has a strong chance to take it with Dirty Computer. She made an album that celebrated her sexuality while also advocating for her art as an openly LGBTQ black woman. It’s an accomplished set that defines so much about the past year, musically and culturally.
Unterberger: If we’re talking about year-defining, we probably can’t do much better than Childish Gambino’s incendiary “This Is America,” or Cardi B, Bad Bunny and J Balvin’s cross-cultural “I Like It,” for song of the year. The populist choice here, though — and this award tends to go to more traditional pop-rock songs — is Lady Gaga and Bradley Cooper’s “Shallow.”
I’m more than slightly worried that record of the year will end up going to Post Malone’s 21 Savage-featuring “rockstar,” a genre-mashing major hit from a superstar well-liked within the industry. If the first hip-hop winner in the category’s history comes from a white lead artist, the internet and media backlash we saw over Bruno and Adele’s recent big wins will be no preparation at all for the shitstorm we’ll witness in 2019.
Williams: “Shallow” feels very much like a “safe” bet in a makes-all-the-sense-in-the-world way. “This Is America” would be a fairly bold win: Would it be framed as proof that the Grammys can celebrate topical art — and hip-hop overall — or as a reaction to backlashes of years past?
Unterberger: Here’s my biggest question: If you were Neil Portnow, presiding over your last Grammys, which artist would you be pulling for the hardest in these major categories? Who gives you the best narrative to ride off into the sunset with? And is a Post Malone sweep the absolute doomsday scenario for your legacy?
Williams: I would think Portnow would like to go out with a show that proves the Grammys are progressing — or at least aren’t as out of touch as believed. So all eyes are on album of the year, but across the board, I’m sure he wants younger, more era-defining artists winning. I believe his biggest fear would be something like a Post Malone sweep, given the push for more diversity and Post’s somewhat polarizing image.
Unterberger: Cardi B winning big would be a best-of-all-possible-worlds scenario: an era-defining artist, a female one — the Grammys need at least some big wins by female artists after Portnow’s “step up” comments last year — and a rapper, showing that hip-hop finally has a real seat at the table in the biggest categories.
H.E.R. still feels a little too anonymous to me to take album of the year. She should have a shot at best new artist, though, which is a relatively weak crop across the board. Ascendant pop star Dua Lipa would be a deserving winner, but H.E.R.’s surprise nomination does have me thinking she has the inside track.
Williams: A big Cardi night would definitely bode well for the Grammys. She’s a phenomenon. As for H.E.R., I think the most likely scenario is taking best new artist. But don’t underestimate the throwback appeal of Greta Van Fleet — the Grammys would love to put a stamp on a young rock act. And I also think Chloe x Halle could make a strong case. The duo made just the right amount of noise this year with an acclaimed debut album, The Kids Are Alright, and the ultimate seal of approval: a spot on The Carters’ On the Run II tour.
Andrew Unterberger is a senior editor for Billboard.com. Stereo Williams is a music and pop culture critic for The Daily Beast.