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Posted by on Feb 15, 2016 in Blog, Essays, Music and Concert Reviews | 0 comments

2016 Grammy Awards Thoughts and Picks




If you were around last year at this time, you witnessed one of the most impressive instances of special events handicapping in quite some time.

Matt Lessinger, who has appeared here frequently as my guest on this site (usually giving out picks on boxing, Mixed-Martial Arts, Oscars, Grammys), successfully rattled off an astoundingly perfect night at the 2015 Grammy Awards, picking several winners including a 10-1 shot as “Album of the Year.”  That’s as amazing a feat as you will see on a public forum and is far better analysis than anything which appears on the conventional entertainment programs which tout “expert advice.”   This is just one reason Lessinger appeared on National Public Radio (NPR) a few years ago, evaluating all the major categories.

Tonight’s 58th Annual Grammy Awards has no appeal to me whatsoever, other than the special tribute segment they’re planning to do for the late great B.B. King, who died last year.  That said, for those who bet offshore, you can find odds on all the major categories and may want to consider Lessinger’s betting advice.  Wagering on special events isn’t legal here in Nevada (yet), so betting offshore remains the only option (unless you’re fortunate enough to live in the U.K. where there are legal betting shops on every street corner — lucky them).

Whether or not you have any interest in popular music or tonight’s show, or not, what follows is a clinic on how to analyze options when it comes to wagering on special events and awards shows.  What follows is Matt Lessinger’s verbatim analysis of the 2016 Grammy Awards:


Last year was a stellar year for Grammy betting, as we nailed Beck for “Best Album” at anywhere between 7-1 and 10-1, and we had the winners in every other major category at or around even money.  Some years are easier than others.  I had a lot of confidence in Beck last year — not that he would surely win, but that we were surely getting value at the price.

This year there’s not as much value, but we’ll take what we can get.  Let’s go through the major categories:



The favorite is Taylor Swift at -140, the second favorite is Ed Sheeran at +200, and then it is a long way back to the other three.  This is not a category that typically springs a big upset.  It is hard to envision anyone winning outside of those two.  The third and fourth choices are Wiz Khalifa and Kendrick Lamar, and unless you are an extremely unique and/or innovative hip-hop artist (see Lauryn Hill, OutKast) then you don’t stand much chance of winning in the open categories.  Wiz Khalifa and Kendrick Lamar are perfectly solid hip-hop acts, but they are not breakthrough artists to the point where they will win open categories.  The longest shot is Little Big Town, which would be an utter shocker.  If you wanted to combine the two favorites, you could for example bet $700 to win $500 on Taylor Swift and bet $400 to win $800 on Sheeran, so you’d be laying $1,100 to win $100.  You would almost certainly pick up a quick C-note, but it’s still not worth it in my opinion.  No bet here.

[Also in my opinion, the song of the year hands down was “Stressed Out” by Twenty One Pilots.  It is everything a song should be in 2015 — catchy, clever, and with broad appeal across age, race, and gender lines — and it is a breakout hit for a group that has struggled in relative anonymity for a long time.  I think it is a travesty that the song/band received zero nominations.  But sadly I don’t get a vote.]



Uptown Funk is the -500 favorite and it will almost certainly win.  Bruno Mars has received twenty Grammy nominations since 2011 (including the two this year) and has only won twice, but one of his wins was against Michael Jackson the year that Jackson passed away, which was quite a shocker.  He has never won in any of the open categories, but he has paid his dues, and all signs indicate that this is the year they will reward him.  Taylor Swift at +600 is tempting, but it also smells like a trap.  The Weeknd is the third choice, and he is one of those intriguing wild cards — if Grammy voters decide they like him, they might pick him across the board.  It feels like an all-or-none situation.  It reminds me of Amy Winehouse in 2008 — out of nowhere, the Grammy voters decided to give her “Song of the Year,” “Record of the Year,” and “Best New Artist,” even though she was not favored in any of those categories.  Somehow Herbie Hancock memorably beat her out for “Album of the Year” at 22-1 odds, or else she would have had a clean sweep.  At any rate, if The Weeknd is someone that Grammy voters decide they really like, then he could spring several upsets.  But given this is his first trip to the big dance, we have to play the percentages and assume he will not be rewarded so quickly.  Ed Sheeran and D’Angelo are distant longshots.  No value in betting such a heavy favorite, therefore no bet.



Meghan Trainor is the -110 favorite, followed by four artists that are unknown to most casual music fans.  This is always the most unpredictable category.  There’s really not much separating the other four nominees, but they are incredibly diverse.  James Bay is a British guitarist who opened for Taylor Swift in England.  Sam Hunt is a country singer from Georgia.  Courtney Barnett is an eclectic songwriter from Australia.  Tori Kelly is a former American Idol contestant from California.  It is truly a category of apples and oranges.  I have no idea who Grammy voters would support among those four.  The real question is whether or not Trainor will win.  My feeling is that Trainor, being the only one that most people have heard of by a large margin, will be overbet by the day of the awards.  The current line of -110 may drop as low as -150 or -200.  At that point, there would be value in scooping up the Field to win “Best New Artist.”  Right now the current line on the Field vs Trainor is -130.  I wouldn’t take that line, but if it drops to even money or better, which it very well might, then I will fire on that.  Trainor being up for Best “New” Artist is somewhat sketchy, especially since “All About That Bass” was from 2014.  I don’t think that is lost on Grammy voters, who may be more inclined to reward someone who truly fits the bill of “New” artist.

My bet:  The Field vs. Meghan Trainor at even money or better.



Finally I think we can find some value.  Let’s start with the second choice, which is Kendrick Lamar at +300.  His odds should be more like +1000.  He is a top hip-hop artist, and I personally think the album (or what I’ve heard of it) is quite innovative, but yet it still does not transcend genres in a way that is typically necessary for a hip-hop artist to win “Album of the Year.”  His album is titled “To Pimp a Butterfly.”  My guess is that most Grammy voters cringe at that title having to be read among the nominees, let alone to name it as the “Album of the Year.”  He is overbet because he is a household name among hip-hop fans, he is associated with Dr. Dre, his album sold almost a million copies, and he has received critical acclaim from Rolling Stone and similar publications.  But for him to win would be signalling a whole new direction by Grammy voters.  It will happen eventually, but we’ll believe it when we see it.

The favorite is Taylor Swift, who is currently at -250.  It is more than likely that she will win, but let’s examine why there might be value in betting against her.  First of all, she is a worldwide household name.  Everyone knows her and knows her music. Her album has sold 8,600,000 copies to date, which is an extraordinary feat in the digital age.  Because so many people have heard her music (as compared to the other nominees) and are fans of hers, they are more likely to throw a few bucks down on her just so they can root for her.  I expect the odds to drop even lower, perhaps to -300 or -400.  Last year was a perfect example. Beyonce opened at -150 for “Album of the Year.”  By the start of the awards, her odds were -300.  This was no surprise.  Her album set records in sales figures, and she was by far the most popular artist.  The money coming in on her is what enabled the odds on Beck to climb to 10-1 by showtime.  We are looking for a similar phenomenon this year.  Watch for Taylor Swift’s odds to drop late on Monday, then look for value elsewhere.

An argument could be made that there is value in any of the other three nominees, especially if their odds climb by Monday as we expect them to.  The Weeknd could be the surprise winner.  As we said earlier, he will most likely either win everything or win nothing.  I am leaning towards the belief that they will consider him too new to win an award that typically goes to a more established artist.  But if you wanted to take a shot on him at +1200, it can’t be that bad of a bet.  Plus, as we said before, the odds on him can be expected to go up by Monday.

Chris Stapleton is a country artist, and at +2000, who knows?  The Dixie Chicks won in 2007 as a longshot.  He’s been around for a long time, but this is his first solo effort, and I would make the same argument that artists rarely get rewarded for their first album.  But especially if his odds climb to +2500 or better, it can’t be a bad bet to put a flyer on him.

The other nominee is Alabama Shakes, currently at +750.  People see “Alabama” and automatically assume they are country, but in fact they are a rock band.  Grammy voters like rock bands (see Beck, Arcade Fire, Steely Dan who all won at long odds).  They have been around for seven years, and Grammy voters like to reward acts that have had some longevity.  Their lead singer is female while other band members are male. Grammy voters have typically rewarded male-female collaborations (see Arcade Fire again, Robert Plant & Alison Krauss, Ray Charles & Norah Jones).  Their album reached #1 on the Billboard 200, yet they are nowhere near the household name that Taylor Swift is, and not even close to Kendrick Lamar either.  This will keep their price high, since their smaller fan base suggests that less casual bettors will support them.  Will Taylor Swift win “Album of the Year?”  It’s more likely than not.  But this is the best value I see in any of the major categories.

My bet:  “Sound & Color” by Alabama Shakes for “Album of the Year” at +750 or better.  Get it now at +750.  Get it on Monday afternoon again, hopefully at a price closer to +1000.


Good luck to everyone,

Matt Lessinger


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