Grammys 2020: Who Will Win and Who Should Win

A look at the strongest prospects for music’s biggest night

Billie Eilish (Art: Ron Hart.)

Who knows what kind of turmoil the Grammys have been thrown into now, or how it will affect the awards or the show itself.

But this was always going to be an exciting year for new and unsung faces, with Rosalia, Big Thief, and DaBaby heading up minor categories and Lizzo, Billie Eilish and Lana Del Rey in the ring for the majors. Still, the Grammys have taught us nothing if not to temper expectations. Here are my cautiously optimistic predictions for a new decade of Grammys, which we already know will never be the same.

Best Rap Song

YBN Cordae feat. Chance the Rapper, “Bad Idea”
Rick Ross feat. Drake, “Gold Roses”
21 Savage feat. J. Cole, “A Lot”
Nipsey Hussle feat. Roddy Ricch & Hit-Boy, “Racks in the Middle”
DaBaby, “Suge”

Should Win: Why are the rap categories a surprising letdown this year? DaBaby is the one true representative of what a great rap year 2019 was even if “Suge” was a fairly pedestrian smash, but it still slaps. YBN Cordae’s harmless laid-back pop, pro forma Rick Ross and Drake, and (sorry) Nipsey Hussle were all a bit too bland while firecrackers like Megan Thee Stallion were reigniting the genre. Give it to “Suge.”
Will Win: Since we’re getting a surprising Nipsey Hussle tribute tonight, you better you bet he’s getting it.


Best Rap Performance

J. Cole, “Middle Child”
DaBaby, “Suge”
Dreamville feat. J.I.D., Bas, J. Cole, EARTHGANG, and Young Nudy, “Down Bad”
Nipsey Hussle feat. Roddy Ricch & Hit-Boy, “Racks in the Middle”
Offset feat. Cardi B, “Clout”

Should Win: Dreamville serves the purpose of getting some unlikely names into the noms (J.I.D.! Young Nudy!) and J. Cole’s own solo cut, “Middle Child” surprised everyone by being one of his best. DaBaby deserves at least one of these, but if you’re gonna give Cole two nominations, he may as well get one.
Will Win: There’s no reason to believe Nipsey doesn’t sweep, but “Suge” would be nice.

Best Rap Album

Dreamville, Revenge of the Dreamers III
Meek Mill, Championships
21 Savage, I Am > I Was
Tyler, the Creator, Igor
YBN Cordae, The Lost Boy

Should Win: Why are these so unremarkable? The only thing close to a great rap album here is Meek’s oddly unsung comeback, but Tyler’s earned his art-damaged reputation as much as Thom Yorke has, so whatever.
Will Win: Tyler, the Creator.

Best Music Video

The Chemical Brothers, “We’ve Got to Try”
Gary Clark Jr., “This Land”
FKA twigs, “Cellophane”
Lil Nas X feat. Billy Ray Cyrus, “Old Town Road (Remix)”

Tove Lo, “Glad He’s Gone”

Should Win: It’s completely astounding that Billie Eilish’s “Bad Guy” was not nominated here, but with love to instant classic “Old Town Road,” that gives Tove Lo’s unexpectedly great “Glad He’s Gone” clip all the more chance to shine.
Will Win: Please let “Old Town Road” whomp FKA twigs.

Best Country Album

Eric Church, Desperate Man
Reba McEntire, Stronger Than the Truth
Pistol Annies, Interstate Gospel
Thomas Rhett, Center Point Road
Tanya Tucker, While I’m Livin’

Should Win: Pistol Annies are the greatest country configuration of our era but that doesn’t mean the Academy will recognize it. Interstate Gospel deserves whatever recognition it can get though.

Will Win: With Brandi Carlisle grandmothering her in, Tanya Tucker’s gonna get the real comeback treatment.

Best Alternative Music Album

Big Thief, U.F.O.F.
James Blake, Assume Form
Bon Iver, I,I
Vampire Weekend, Father of the Bride
Thom Yorke, ANIMA

Should Win: The usual yawns: James Blake, Bon Iver, anything Thom Yorke happened to do that year. That leaves Vampire Weekend’s predictably excellent fourth album and upstarts Big Thief, who won me over more or less. This win would mean more to them than Ezra Koenig, so let’s give him a run for his money.
Will Win: If it’s got to be a white dude, please let it be Koenig over Justin Vernon, who’s explicitly rejected this institution and yet his employees keep canvassing for his recognition.

Tune in tonight to catch the Grammy Awards on CBS

Best Rock Song

Tool, “Fear Inoculum”
The 1975, “Give Yourself a Try”
Vampire Weekend, “Harmony Hall”
Brittany Howard, “History Repeats”
Gary Clark Jr., “This Land”

Should Win: This is the most fun category of this entire batch, pitting Tool against Vampire Weekend, Gary Clark Jr. against the 1975. Not only do these five acts sound nothing alike, they all occupy completely different media spaces. Brittany Howard isn’t my personal idea of mind-blowing but she’s an excellent singer and performer and Jaime was as acclaimed as anything else, give her a rock award.

Will Win: God, who knows. It could be Ms. Howard. It could be Tool. It probably won’t be the 1975, despite their thirst.

Producer of the Year, Non-Classical

Jack Antonoff (Kevin Abstract, Taylor Swift, Lana Del Rey, Red Hearse)
Dan Auerbach (The Black Keys, Yola, Leo Bud Welch, Dee White, Night Beats, The Gibson Brothers)
John Hill (Young the Giant, Khalid, Carly Rae Jepsen, Cage the Elephant, Imagine Dragons)
FINNEAS (Billie Eilish)
Ricky Reed (Maggie Rogers, Lizzo, SZA, Maren Morris, FIDLAR)

Should Win: FINNEAS! The Billie Eilish album is a producer’s career album, especially in headphones.

Will Win: This is a duel between Antonoff and Reed, and I personally prefer Reed, who has as good a chance of anybody with all of Lizzo’s noms.

Best Pop Vocal Album

Beyoncé, The Lion King: The Gift
Billie Eilish, When We All Fall Asleep, Where Do We Go?
Ariana Grande, thank u, next
Ed Sheeran, No. 6 Collaborations Project
Taylor Swift, Lover

Should Win: Bizarre, all of these albums, even Sheeran’s not-bad hip-hop mixtape, are better than Beyoncé’s lame reprise of the astounding Black Panther concept. But only Billie and Ariana made classics. Give this to Ari, who doesn’t have the edge in any other categories.

Will Win: It will be Billie and that’s completely fine.


Best Pop Duo/Group Performance

Ariana Grande & Social House, “Boyfriend”

Jonas Brothers, “Sucker”

Lil Nas X feat. Billy Ray Cyrus, “Old Town Road (Remix)”

Post Malone feat. Swae Lee, “Sunflower”

Shawn Mendes feat. Camila Cabello, “Senorita”

Should Win: “Old Town Road” vs. four different flavors of mild sauce? This is the category Lil Nas X and Billy Ray Cyrus’ alliance was born to steal.
Will Win: “Old Town Road.”


Best Pop Solo Performance

Beyoncé, “Spirit”
Billie Eilish, “Bad Guy”
Ariana Grade, “7 Rings”
Lizzo, “Truth Hurts”
Taylor Swift, “You Need to Calm Down” 

Should Win: I want Lizzo to have everything, I really do. But “Truth Hurts” is a three-year-old fluke bested by almost any of her proper 2019 tracks and “Bad Guy” is a stone classic. Poor Ari’s weakest hit just doesn’t cut it here either. And I actually really like Taylor’s LGBTQ nod, but she’s got enough Grammys.

Will Win: “Truth Hurts,” and why not?

Best New Artist

Black Pumas
Billie Eilish
Lil Nas X
Maggie Rogers
Tank and the Bangas

Should Win: This battle’s entirely between Billie and Lizzo, but the incredible Rosalía was shut out of everything else but Best Latin Rock/Urbano Album, and she deserves to eat everyone in attendance.

Will Win: I’m gonna say Billie.


VIDEO: Lizzo “Truth Hurts”

Song of the Year

Lady Gaga, “Always Remember Us This Way”
Billie Eilish, “Bad Guy”
Tanya Tucker, “Bring My Flowers Now”
H.E.R., “Hard Place”
Taylor Swift, “Lover”
Lana Del Rey, “Norman Fucking Rockwell”
Lewis Capaldi, “Someone You Loved”
Lizzo, “Truth Hurts”

Should Win: It would be nice for “Truth Hurts” to snag this after all that songwriter credit drama, even if it’s absurd that “Juice” was shut out. Maybe in 2023, “Juice.”

Will Win: I’m putting my money on Lizzo.

Album of the Year

Bon Iver, I,I
Lana Del Rey, Norman Fucking Rockwell!
Billie Eilish, When We All Fall Asleep, Where Do We Go?
Ariana Grande, thank u, next
H.E.R., I Used to Know Her
Lil Nas X, 7
Lizzo, Cuz I Love You [Deluxe Edition]
Vampire Weekend, Father of the Bride

Should Win: Some of the strongest albums to see nominated her in recent memory, but I’d be happiest to see Lizzo rule in a category that’s historically shortchanged black women.

Will Win: Unless Bon Iver pulls a Beck, this one feels like it could be in the bag for Billie.

Record of the Year

Bon Iver, “Hey, Ma”
Billie Eilish, “Bad Guy”
Ariana Grande, “7 Rings”
H.E.R., “Hard Place”
Khalid, “Talk”
Lil Nas X feat. Billy Ray Cyrus, “Old Town Road (Remix)”
Lizzo, “Truth Hurts”
Post Malone feat. Swae Lee, “Sunflower”

Should Win: “Bad Guy.”
Will Win: Unless it’s somehow “Old Town Road,” it’s Billie, duh.


VIDEO: Billboard 2020 Grammy preview

Latest posts by Dan Weiss (see all)

 You May Also Like

Dan Weiss

Dan Weiss is a freelance writer living in New Jersey.

Leave a Reply

Your email address will not be published. Required fields are marked *