The Official Barstool Sports Preview and Prediction Blog For Tonight's 66th Annual Grammy Awards. BONUS - Barstool Personalities Predictions

Everybody's favorite award show is tonight evening. That's right, the 66th Annual Grammy Awards. A gathering of the best in American music to honor the best recordings, compositions, and artists from October 1, 2022, to September 15, 2023, as chosen by the members of The Recording Academy. That time of year when the music industry pats itself on the back and we, the mere mortal audience, get to critique fashion choices and question the existence of some categories. 

This year's 66th edition promises to be a roller coaster of emotions, talent showdowns, and, a few "what were they thinking?" moments.

I hit up some of the more musically inclined and outspoken Barstool personalties for their thoughts and opinions on the categories and nominees this year and will list them out as we go through the big categories. 

PERFORMANCES

Let's be honest. The Grammy awards themselves are usually the most boring parts of the night. What makes the entire thing worth tuining in for every year are the unforgettable performances. You might roll your eyes at that statement but don't forget that the last two years in a row we've gotten these Chris Stapleton duets which are nothing short of legendary-ary.

Let's be honest, the performances are why we all tune in. 

The big rumor of the night is that Luke Combs, nominated for Best Country Solo Performance, will be performing "Fast Car" with Tracy Chapman herself. Which should be amazing.

This year, expect the unexpected. SZA's set to perform, and if her music videos are anything to go by, we're in for a treat. Or a trip. Probably both.

If you've been anywhere near a streaming service this past year, you know why this is a big deal. Her album "SOS" has been on repeat in every corner of the globe. Expect her performance to be a blend of stunning vocals, ethereal visuals, and maybe, just maybe, an on-stage surprise that'll have Twitter buzzing for hours. (My money is on r&b royalty joining her on stage for a surprise guest appearance.)

Billie Eilish is back, and she's not just dipping her toes in the Grammy pool — she's doing cannonballs. With six nominations including Record of the Year for "What Was I Made For?," her performance is bound to be a highmark moment of the night.

Billy Joel is emerging from his pop songwriting sabbatical to grace the Grammy stage, presumably because he finally found the switch to "Turn the Lights Back On." It's his first new pop song since 2007.

Then there's Burna Boy, whose name alone suggests you're in for something fiery. Nominated for the first-ever Best African Music Performance, he's not just representing Nigeria; he's carrying the torch for an entire continent's rich musical heritage. Anticipate a performance that's as much a celebration of African music as it is a showcase of Burna Boy's undeniable charisma and energy. If you're curious about the future of global music sounds, Burna Boy's set is a must-watch.

Adam Blackstone isn't just a name you'll see in the credits; he's bringing jazz back to the forefront with a nod for Best Jazz Performance for "Vulnerable (Live)." If jazz had a LinkedIn profile, Blackstone would be its most endorsed skill. Expect a performance that's smoother than your grandpa's old scotch.

All of our favorites, Dua Lipa, with her double nod for the infectious "Dance the Night," is set to prove why she's pop royalty. Here's hoping we get another short skirt and pole dance to accompany.

One of my big favorites to clean up this year with six nominations, Olivia Rodrigo is ready to prove that "drivers license" was just the beginning. Her performance of "Vampire" is bound to leave a wake of crushed male egos behind it. That song cuts so deep.

We've also got confirmed performances from Travis Scott (yawn), Terrace Martin, Joni Mitchell, Gaby Moreno, Harvey Mason Sr, Kirk Franklin, and Robert Glasper. 

Those are really the only announced performances, but we all know the Grammys like to keep us on our toes. While we've got some confirmed performers, expect a few surprise acts to pop up. 

CATEGORIES AND PREDICTIONS

A reminder that we will be live streaming tonight, throw us a tune in. White Sox Dave has been hammered since 8am so it should be entertaining.

Thanks to Robbie Fox, Feitelberg, and Kelly Keegs for taking literally 30 seconds to respond to the email I sent this week. Those who were polled but were too busy or unavailable - White Sox Dave, Chaps, Rone, Nick Turani, Kevin Clancy, Nate, Chief, and Wayne Jetski.

Here's my big question for tonight. Is Taylor Swift rolling solo tonight? Or are we going to get a Kelce sighting to set the internet on fire and steal all the talk from the entire night? It's a hop skip and a jump from LA to Vegas so I don't think it's that crazy or out of the question to ask. 

BEST NEW ARTIST

Gracie Abrams
Fred Again
Ice Spice
Jelly Roll
Coco Jones
Noah Kahan
Victoria Monét
The War and Treaty

Best New Artist is like the wild west this year. Victoria Monét seems poised to take it, but with contenders like Ice Spice and Jelly Roll, it's as open as my local 24/7 diner. Monét's got the nominations to back it up, but in the land of the Grammys, surprises are as common as misplaced acceptance speeches.

ROBBIE FOX - Noah Kahan
I love Jelly Roll but this just feels like the year of Noah Kahan. He was booked in a co-headlining slot at Oceans Calling and very easily could've been the headliner with the crowd he drew. Dude is taking over folk/indie/pop right now.

Feitelberg - Noah Kahan. New England’s only win of the year. 

Kelly Keegs -Ice Spice

Ice Spice by a mile. I love everyone else on this list and it's a shame they have to go up against a new juggernaut, but Ice Spice has blown up more in the past year than anyone else. With the help of Tiktok and Taylor Swift, I don't see a world where she doesn't win this.

Dante - As much as I'd love to see Fred Again shock the world and take home a major award for the electronic dance community, I have a brain and know it's a 1% chance. I gotta go with my gut and go with Jelly Roll here. It's his year, he's on fire, and the Grammys needs clicks. We all saw the speech he gave at the CMA's and the Grammy's wants all of that.

Best pop solo performance

Miley Cyrus – Flowers
Doja Cat – Paint the Town Red
Billie Eilish – What Was I Made For?
Olivia Rodrigo – Vampire
Taylor Swift – Anti-Hero

And then there's Best Pop Solo Performance. Will Taylor Swift's "Anti-Hero" reign supreme, or will Billie Eilish swoop in with "What Was I Made For?" It's a toss-up, and my money's on the underdog. Because who doesn't love a good underdog story?

Robbie Fox - Miley Cyrus – Flowers
See above x2

Feitelberg - Taylor Swift. Damn I didn’t know she was gonna come up again, I would’ve structured my earlier explanations differently. 

Kelly Keegs - This is another tough one - I think either Billie or Taylor take this one, whoever doesn't win SOTY. Miley and Olivia put up a good fight, but they fall short of Taylor and Billie IMO. Doja Cat's Paint The Town Red was also EVERYWHERE though, so she could easily swoop in for the upset.

Dante - Olivia Rodrigo - vampire. I haven't heard a song like this in a long time. Picture every woman you've ever hurt, combined with every woman your friends have ever hurt, multiplied by every Lifetime movie depicting men as absolute scum, and have a poet write a 3 minute song about it and this would be the result. It's pretty amazing. This girl is the real deal. 

Best Rap Performance

Baby Keem and Kendrick Lamar – The Hillbillies
Black Thought – Love Letter
Drake and 21 Savage – Rick Flex
Killer Mike – Scientists and Engineers (ft André 3000, Future & Eryn Allen Kane)
Coi Leray – Players

For the hip-hop heads, Best Rap Performance is looking spicy. Kendrick Lamar could extend his winning streak, but Killer Mike's "SCIENTISTS & ENGINEERS" is the track with the buzz. And if Coi Leray's "Players" takes it, I'll eat my hat. Figuratively, of course.

Robbie Fox - Black Thought – Love Letter
I just listened to all of these songs for the first time. Black Thought went acapella and captivated me for 4 minutes straight so I'm giving it to him. That Drake song is great tho.

Feitelberg - Killer Mike. I didn’t see the performance but I like how him and Bernie Sanders are friends. It feels like something that would happen in a cartoon. 

Kelly Keegs - Wow, I didn't think I was going to get reminded how OLD I am while writing this. Rap isn't my best genre, I've fallen behind on all of the new artists and songs that don't include Meg the Stallion or like, Cardi B, and I don't know a single song on this list. Might as well give it to Drake then!

Dante - Killer Mike. I wrote like 10 blogs about this song and album.

Best Rock Performance

Arctic Monkeys – Sculptures of Anything Goes
Black Pumas – More Than a Love Song
Boygenius – Not Strong Enough
Foo Fighters – Rescued
Metallica – Lux Æterna

Robbie Fox - Foo Fighters – RescuedNot the song I would've nominated for this award (that goes to 'Under You') but still my favorite song nominated by a longshot.

Feitelberg-  Black Pumas. I haven’t heard abt them since their last Grammy performance and I find that romantic. They’re like a good buddy you see every few years and are like oh yeah that dude fuckin rules, we should hang out more. Then you don’t and have the same realization when you bump into them three years down the line.

Kelly Keegs - Boygenius – Not Strong Enough

It's the year of Boygenius! This crew is due for their accolades, they had an incredible year, and they deserve it. In reality, it'll probably end up going to one of the OGs (Foo Fighters, Metallica) but it'd be nice for Boygenius to take this one home.

Dante - Anybody but the lesbian supergroup boygenius for me here. Colin's favorite. Which probably means they win it. My heart says Black Pumas but my head said Foo Fighters. They've had a brutal stretch. 

Best Country Solo Performance

Tyler Childers – In Your Love
Brandy Clark – Buried
Luke Combs – Fast Car
Dolly Parton – The Last Thing on My Mind
Chris Stapleton – White Horse

Best Country Solo Performance might just go to Luke Combs for his heartfelt rendition of "Fast Car." But never underestimate the power of Dolly Parton, the queen of everything, with "The Last Thing On My Mind."

Robbie Fox - Chris Stapleton – White Horse
The new Stapleton album is incredible - as expected. It's like Stapleton meets R&B/motown with all of the sick bass grooves across the whole record, but 'White Horse' is my favorite track and NEEDS to be Stapleton's new opener. That intro build up is orgasmic.

Feitelberg - write in for Zach Bryan. It’s called loyalty, look it up. 

Kelly Keegs - Luke Combs – Fast Car

Not a chance anyone but Luke Combs wins this right? I've heard his version of Fast Car more than I've heard the original at this point. There are people all over the world who think this IS the original. He did a beautiful job covering a fantastic song, he deserves it.

Dante - Luke Combs. This song was colossal and they're performing it together (RUMOR) tonight. 

Record of the Year

Jon Batiste – Worship
Boygenius – Not Strong Enough
Miley Cyrus – Flowers
Billie Eilish – What Was I Made For?
Victoria Monét – On My Mama
Olivia Rodrigo – Vampire
Taylor Swift – Anti-Hero
SZA – Kill Bill

Record of the Year is turning into a battle royale with an all-female nominee list for Best Pop Solo Performance that's about as predictable as my Spotify Wrapped. Miley Cyrus' "Flowers" might have been the anthem for every post-breakup road trip, but don't count out the underdog Victoria Monét with "On My Mama." And if Taylor Swift's "Anti-Hero" doesn't win something, we might have to check if the universe is still in balance.

Robbie Fox - 

Miley Cyrus – FlowersI've heard this song ten thousand times and I'm still not sick of it. Can't say that about the rest of the options.

Feitelberg  - Taylor Swift Antihero. It’s Taylor Swift. 

Kelly Keegs - SZA - Kill Bill 

My gut tells me Anti-Hero outplayed all of these other songs but….SZA needs a grammy. Kill Bill was AWESOME, and this could be her best shot. If we want to keep Gen Z interested in the Grammys, this one goes to her. 

Dante - Olivia Rodrigo - same thing I said above. This girl's sophomore album guts is fucking amazing. It has real instruments, and a nostalgic grunge feel to it. And it works! 

Song of the Year

Lana Del Rey – A&W
Taylor Swift – Anti-Hero
Jon Batiste – Butterfly
Dua Lipa – Dance the Night
Miley Cyrus – Flowers
SZA – Kill Bill
Olivia Rodrigo – Vampire
Billie Eilish – What Was I Made For?

Now, for the Song of the Year, where the songwriters get their moment in the sun. Will it be Billie Eilish with "What Was I Made For?" or Miley Cyrus finally getting her Grammy moment with "Flowers"? It's anyone's game, and if Lana Del Rey doesn't win for "A&W," I'm starting a support group.

Robbie Fox- Song of the year

Miley Cyrus – FlowersSee above

Feitelberg - Taylor Swift Antihero. Take a wild guess why pal. 

Kelly Keegs - Billie Eilish – What Was I Made For?

This one is tough. Big arguments could be made for Kill Bill and Anti-Hero, but the Barbie crowd might burn the place down if Dua Lipa or Billie Eilish don't come away with this. Dua had the more fun song, but Billie's "What Was I Made For?" is touching, beautifully written/mixed, and has already won a handful of high status awards this season. I think I'm gonna go with Billie.

Dante - Miley Cyrus - Flowers. Her best song of her career. She is longggggggg overdue. 

Saved the best for last, the big shambola: Album of the Year. The lineup reads like the who's who of music royalty, with Taylor Swift's "Midnights" ready to make Grammy history if it snags the win. But hold on, not so fast my friend, - SZA's "SOS" is the critics' darling, and Jon Batiste, the dark horse with his "World Music Radio," might just gallop past the competition. Remember last year? Yeah, neither do I, but Batiste does, and he's back for more.

ALBUM OF THE YEAR 

Jon Batiste – World Music Radio
Boygenius – The Record
Miley Cyrus – Endless Summer Vacation
Lana Del Rey – Did You Know That There’s a Tunnel Under Ocean Blvd
Janelle Monaé – The Age of Pleasure
Olivia Rodrigo – Guts
Taylor Swift – Midnights
SZA – SOS

In a world where our playlists are as diverse as our palates, the Grammys offer a rare chance to see the industry's best and brightest all in one place, doing what they do best. It's where genres collide, unexpected collaborations are born, and once in a while, we witness a performance that becomes a part of music history.

Robbie Fox - Olivia Rodrigo – GutsBasic bitch pick? Maybe. GUTS is a legit great pop punk/ballad album tho, and I think it's actually helping the next generation get into guitar music.

Feitelberg - Taylor Swift Midnights. Ditto. 

Kelly Keegs -Taylor Swift – Midnights

I think this is the one that Taylor takes home. With so many great songs/records coming out this year, it's hard to think that Taylor will sweep like she has in the past, but there's not a chance she doesn't walk away with at least one. Midnights has created SO much conversation, broken countless records, and has been steadily popular since its release in 2022. It deserves its flowers.

Dante - Olivia Rodrigo - guts. We are witnessing a super-duper-duper star in the making. This girl is special, real talent.

Here's our Grammy breakdown and predictions. We've been busy with the Backstage project. 

We interviewed Ruston Kelly last week

We interviewed Joey Vallance and Brae this week at HQ.

p.s. - Bill Maher keeps staying hot