The Grammy Awards aren’t just about music and entertainment. For years, a few sharp bettors have been scoping out each category and winning money where there’s value. Matt Lessinger is one of the few experts with a documented winning record betting on the Grammys, and this year, he shares his picks for the 2020 Grammys — and the reasoning behind them — with the readers of OnlineGambling.com.

grammy awards
Some sharp bettors seem to have cracked the code for figuring out who is most likely to take home a Grammy. If you can get down a bet or two, the announcement of winners might be music to your years. (Image: MJ Photos)

The 62nd annual Grammy Awards show takes place in Los Angeles at the Staples Center, Sunday, 5 pm PT.

It’s no exaggeration to say nobody in the world has picked more Grammy winners for profit over the past seven years than Lessinger. He’s a gambling writer, author, and entertainment speculator who has opined on Grammy odds for multiple media outlets over the years, including National Public Radio.

With his permission, the analysis below is from an annual email exchange I enjoy with Lessinger, wherein he seeks to help me understand why and where he sees an advantage.



Matt Lessinger bets on the Grammys
Grammy odds expert Matt Lessinger. (Image: Lessinger Gaming)

Matt Lessinger’s Grammy Insights

History of Grammy Bets

Last year really put a wrench in my overall analysis of the Grammys. It wasn’t so bad that Kacey Musgraves won Album of the Year as the +130 favorite. From a betting perspective, you accept that and move on, because there was no value in betting her, much like there was no value in Taylor Swift in 2015 (priced at -300) or Mumford and Sons in 2012 (priced at -200).

What was shocking for me was to have Childish Gambino win both Record of the Year and Song of the Year. If anyone had wanted to wager on him in either category at his +150 price, I would have gladly taken large amounts of their action, and I’d have paid out like a slot machine. He didn’t even show up for the Grammys, which tells me he didn’t think much of his chances either. So while his wins may signal a shift in Grammy voter preferences, I’m going to stay stubborn for at least one more year.

Fade Lizzo in 2020?

The entire 2020 Grammys can be broken down into three categories:
  1. Billie Eilish
  2. Lizzo
  3. Everyone Else

Objectively, this was a weak year for music, and I say that because two new, unproven artists are the favorites in every category. I could make the case to fade both of them in every category based on their youth and short careers, but the problem is that there are no standouts in the rest of the field either. So the plan is to take some flyers on longshots and hope to get lucky … but let’s also do a more careful analysis.

For starters, we have to take a stand against at least one of the two favorites, and in my opinion, Lizzo is the fade. Her music, while catchy, is not what Grammy voters would traditionally vote for. Her antics outside of her music (i.e, substantial naked images) are not going to earn her any additional votes either.

Billie Eilish, 18, is completely clean-cut — she still lives at home with her parents, and when she tours it’s with family. Her music is much closer to what Grammy voters traditionally pick. The only thing working against her is her age.

All odds are based on Bovada’s line as of Jan. 23, which are the lines at which I placed my bets. But I will also be looking for better lines on other sites, and possibly placing further action.

Best New Artist

Billie Eilish is the -325 betting favorite, and she should win. But Lizzo is +150, and has maybe a 25 percent chance of winning. Anyone else would be a  shocker. No value, therefore no bet.

Song of the Year

“Truth Hurts” (Lizzo) is the +130 favorite, and “Bad Guy” (Billie Eilish) is +160. They’re followed by “Lover” (Taylor Swift) at +500.

In general, any bet that fades Lizzo likely has value. Eilish at +160 has minimal value, and Swift should probably be higher than +500. Out of the five longshots, most of whom would be total shockers, the one that catches my eye is “Norman Fucking Rockwell” (Lana Del Rey) at a solid +3500.

I’m not saying it will win, but I feel confident it has better than a 3 percent chance of winning.

Record of the Year

“Old Town Road” (Lil Nas X) is the -175 favorite, and then “Bad Guy” is +175, and “Truth Hurts” is +625. Even though I understand the difference between Record of the Year and Song of the Year in theory, the same artist wins both of them so often that it’s hard to understand the huge disparity in betting lines. Lil Nas X could certainly win, but again, where’s the value?

Eilish has some value, but I chose a route different than betting her individually, as you will see.

Album of the Year

Eilish is -220, and that’s probably close to a fair line. Lizzo is +400. If she wins this, or any other category, I’ll get smoked this year. So be it.

Ariana Grande is +450, but there is no buzz surrounding her album at all, so I don’t like her chances.

The longshots are where it gets interesting. Lil Nas X and H.E.R. are both +4000, and they should each probably be +20000, so forget them. But then you have Bon Iver (+2500) and Vampire Weekend (+3500) who both have a puncher’s chance based on their longevity, overall body of work, and past Grammy wins. Album of the Year tends to reward longevity far more than any other category, so that bodes well for the longshots.

And then, in my opinion, the one who stands the best chance of pulling an upset is Lana Del Rey at +700. Not only has she had a lengthy career — way longer than any of the favorites — but also her current album is widely considered her best. She’s 34, which makes her older than the favorites, but not too old. And her throwback style that pays tribute to older styles of music definitely sits well with typical Grammy voters.

Betting on a Sweep

This year, Bovada has posted an interesting bet. They are offering +600 if Billie Eilish sweeps all four categories. Here’s the thing … if you were treating it as a straight parlay, then +600 wouldn’t be enough of a price. But a straight parlay only deals with uncorrelated wagers, and I would argue that’s not the case here.

Record of the Year and Song of the Year go to the same song often enough — almost half the time — that knowing the winner of one would definitely change the odds of the other. So, for example, if Eilish wins either ROTY or SOTY (each of which I would consider betting independently), then her odds of winning the other just improved. If she wins both of these, it would be shocking for her to not also win Best New Artist. And then it’s just a question of whether or not the Grammys will award her Album of the Year for the sweep.

So rather than bet her in the individual categories, I opted for this group wager, with hedges on the longshots that I think could get in her way. So if Lizzo or Lil Nas X have a good night, then I will have a bad one, but that’s the risk I’m willing to take.

Matt Lessinger’s 2020 Grammy Award Wagers

  • Billie Eilish to sweep all four major categories: YES at +600 (4 units)
  • Lana Del Rey to win ALBUM OF THE YEAR: +700 (3 units)
  • Bon Iver to win ALBUM OF THE YEAR: +2500 (1 unit)
  • Vampire Weekend to win ALBUM OF THE YEAR: +3500 (1 unit)
  • Lana Del Rey to win SONG OF THE YEAR: +3500 (1 unit)

You can follow entertainment handicapper Matt Lessinger @mlessinger. And you should, of course, already be following @OGambling

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