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5 Grammy Awards Sleepers Worth a Bet in 2021

| January 13, 2021 11:28 am PDT
2021 Grammy Awards Sleepers

The 2021 Grammy Awards are just around the corner. They’re not as close as music fans were expecting, but the wait won’t be intolerable.

Originally slated for January 31st, the 63rd installment of the Grammys will be pushed back due to ongoing COVID-19 concerns. The show must go on, but in this case, it’ll go on come March 14th.

The 2021 Grammys are still going to happen, so it will still pay to read up on the top nominees, and plan your betting ahead of time.

You’ll also want to know where to bet on the 2021 Grammys, while taking a look at some sneaky value picks may not be a bad idea, either.

If you want to aim high with your 2021 Grammys bets, consider my favorite Grammys sleepers.

Hollywood’s Bleeding to Win Best Album (+600)

This is about as deep of a dive as I’ll take here. Post Malone’s third LP is arguably his best yet, and he’s come close to getting the big honor before.

To be clear, Taylor Swift is the big favorite with Folklore (-260), and Dua Lipa’s Future Nostalgia (+300) is easily the top challenger.

More likely than not, one of those albums gets the nod. 

However, Post Malone shouldn’t be brushed off here. He put together a bit of a masterpiece, and way back in June, Hollywood’s Bleeding was among Billboard’s best bets to win Album of the Year at the 2021 Grammy Awards.

Post Malone probably won’t win, but if you don’t want to eat the money with Swift and aren’t sold on Lipa, he’s looking pretty appealing with these +600 odds over at MyBookie.

Everything I Wanted to Win Record of the Year (+1000)

This isn’t about probability or a lack of competition, which you could argue with Album of the Year. This is about name recognition and good old fashioned betting value.

Billie Eilish dominated the 2020 Grammys. This is not her year when you compare it to last year, but she still put out some great music.

One track that kept her relevant was “Everything I Wanted”, which is thoroughly captivating, and rather dark. The music video aligns with it perfectly, but it’s just as riveting live.

Eilish could make history here, as she obviously won for this same category in 2020. This record did reach the top-10 this year, so it’s got the staying power to give top favorites “Don’t Start Now” and “Savage” a run for their money.

Like I said, though, this is a price play. Eilish is one of the biggest stars on the planet at this point, it’s a beautiful track, and the odds are very tempting.

Kaytranada to Win Best New Artist (+2000)

This category is actually loaded this year. Billie Eilish was the easy call in 2020, and it’s probably inarguable that Megan Thee Stallion (-500 favorite at most entertainment betting sites) is the clear winner.

That said, you have to bet a lot of money to make backing Megan Thee Stallion worth it. It may be better to just ignore this bet, or chase a little upside.

To be frank, you can get it from a lot of areas. Doja Cat (+400) is also phenomenal, Phoebe Bridgers (+450) is a rising artist with a feathery tone, and Ingrid Andress (+1500) is as smooth as anyone.

I think you can talk yourself into a lot of different value bets when looking to bet on the Best New Artist this year, but I’d either go hard at Megan Thee Stallion or swing for the fences with Kaytranada.

Kaytranada was already making a name for himself as a blend master, but he took things to a whole new level with the 2019 Bubba.

Laced with big names, heart-pumping electronica, and rich emotion, Bubba stands out as a bit of a tour de force, and is among the best albums of 2020.

I’ll be the first to tell you that Megan Thee Stallion deserves this award (and is almost certainly winning it), but if you want value, Kaytranada is a worthwhile punt.

Circles to Win Song of the Year (+1000)

The Grammy Awards tend to highlight one artist who dominated the music industry over the past year, and in this past year that figures to be Taylor Swift.

She’s probably winning Album of the Year, and it’ll be a mild surprise if “Cardigan” also doesn’t take home Song of the Year.

But she is not the heavy favorite here that she is elsewhere. Dua Lipa’s “Don’t Start Now” is a very real challenger, and then you have Queen Bee’s “Black Parade’.

There is value littered throughout the Song of the Year category, to be honest. H.E.R.’s “I Can’t Breathe” is appealing at +700, and if Eilish can’t take home Record of the Year, maybe consider her at +900.

But the artist and song that stands out the most is Post Malone and “Circles”.

Not only is this song stuck on repeat in our heads, but it seems to define the past year in music.

It’s the biggest reason Post Malone is (kind of) in the running for Album of the Year. He probably won’t get the nod there, though, so it could make perfect sense for this killer track to get the consistently nominated Malone his first Song of the Year win.

While unlikely, the +1000 odds make this one worth the risk.

Shameika to Win Best Rock Song (+300)

Fetch the Bolt Cutters is probably the best album of the year. It wasn’t even nominated. I don’t get it, you don’t get it. Nobody gets it.

But it is what it is at this point. That isn’t to say Swift and some of the other nominees aren’t deserving, but Fiona Apple (per usual) bared her soul in this album, and also handed out several Song of the Year contenders.

“Shameika” is a layered cake of punches and wit that pulls you in right away and hammers a barrage of beats and sharp words. It is beautifully upbeat and harrowing, all in the same breath.

Is it a rock song? Not necessarily, but who cares? It’s a great song, and even has a great story behind it.

Fionna Apple needs to be honored in some way this year. Here’s to hoping the Grammys pay her the respect she deserves, while getting bettors some solid value in the process.


If you’re getting ready to bet on the 2021 Grammy Awards, just keep in mind that things remain pretty fluid.

Everyone got hit with a surprise when the news dropped that the event would be backed up to March, and that leaves way more time for things to change.

I mostly refer to pricing for the major categories, as whispers will meander through the entertainment industry, and Grammys odds will surely be altered numerous times.

For now, you can only work with what’s out there, and what the top entertainment betting sites give you. Take all of the information and rumors with a grain of salt – even my 2021 Grammys sleepers – and for the most part, stick to the top favorites and their immediate challengers.

That said, it’s not like there have been Grammys upsets before. Shockers do happen at the Grammy Awards, and if you can hit even one Grammys sleeper, it’ll be worth it.

With the 63rd Grammys delayed a bit, you may need some extra entertainment betting fodder to pass the time. Hit up our entertainment betting blog for fresh content, or check out the links below.

Noah Davis
Noah Davis

Noah Davis is one of the more diverse writers at GamblingSites.com. Like many of his colleagues, he's a huge fan of both football and basketball. But he also writes about box office records, TV show prop bets, DFS, and all kinds of other subjects.

When it comes to the NFL, Noah's favorite team is the Cleveland Browns. He enjoys cheering them on with his wife and daughter.

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