Even amid all the controversy over the Grammy nominations, somebody is still going to win in all these categories. So, as is our wont, we’re wading into these treacherous waters with our thoughts on who will—and who should—win in each of the Big Four categories. We don’t recommend wagering on the outcome; as has been demonstrated repeatedly, Grammy does what it wants, not always what makes sense. This is how things look going into the holidays; we will naturally reassess afterward. OK, let’s do this.


Lenny: I wouldn’t be surprised to see Taylor Swift or Dua Lipa win in this category. Most of the others are longshots.

Simon: Agreed. My tendency is to think Taylor takes it—partly because folklore was very well received and something of a return to her roots, and partly because she got stiffed on her last two albums.

Lenny: Yes, the Academy is all about the “make good” win. It’s a lot like Scorsese getting Best Picture for The Departed because Oscar screwed up in the past. As far as Dua Lipa goes, Grammy has already anointed her as Best New Artist, so an Album win would be a way of saying she’s fulfilling that promise.

Simon: No doubt. That said, Jhené Aiko fits a lot of Grammy’s criteria—and her record is really something special. And since Summer Walker was shut out, Jhené is carrying the banner for the generation of young female artists who are transforming R&B.

Lenny: Yes, she’s my “should win,” and she might.


Lenny: I say Dua Lipa should win and will win for “Don’t Start Now.” Post Malone’s “Circles” was so ubiquitous that it could; it just doesn’t feel like his year for reasons that have nothing to do with music or the marketplace. Most of the other records cancel each other out. And for my money, nothing that was nominated is as good as “Blinding Lights” or “Adore You.”

Simon: Point taken, but let’s play the hand we’ve been dealt. Dua is my choice for “should win.” But I have a sense that this might be a big “make good” year for Beyoncé, and her “Black Parade” is an opportunity for Grammy to support a positive message while making it up to a great star they slighted in years past.

Lenny: It would be akin to a lifetime achievement award. So, is she your “will win” pick?

Simon: I’m reluctant to say at this point.

Lenny: You’re such a wimp.

Simon: Don’t I know it.

Lenny: But you have to make a pick.

Simon: Or do I?


Simon: I think Taylor is poised to take it for “cardigan,” as Grammy tries to make up for past errors by honoring her songwriting. It seems like several other entries will cancel each other out.

Lenny: I think Dua Lipa will win, though Post could also win for “Circles.” JP Saxe and Julia Michaels should win for “If the World Was Ending.” I personally don’t think “cardigan” is the best song on Taylor’s album.

Simon: I like JP/Julia too and it’s unlike anything else in the category, but I’ll stick with Taylor for “should win.”

Lenny: At least you’re committing to something.


Lenny: In a field that’s missing a number of artists I was sure would get nominated, I think it’s down to Megan Thee Stallion and Phoebe Bridgers—the commercial juggernaut and the critical fave. I think Megan will win and Phoebe should; I’m rooting for Phoebe, as I have been all year.

Simon: My money is on Megan to win. I’d be delighted to see Phoebe or Ingrid Andress take it, though; I think they’re both going to do great things.

Lenny: In any case, Grammy will do what Grammy wants to do. If some of the other artists we thought would end up in this category had made the cut, it would be a lot more dramatic.

Simon: I wonder if we’ll do better than Nate Silver.