Cross-generational Grammy predictions: Will 19-year-old Olivia Rodrigo or 95-year-old Tony Bennett be 2022's big winner?

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·Editor in Chief, Yahoo Music
·9 min read
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Olivia Rodrigo and Tony Bennett, who are 76 years apart in age, are the leading contenders to win Album of the Year. (Photos: Geffen Records, Getty images)
Olivia Rodrigo and Tony Bennett, who are 76 years apart in age, are the leading contenders to win Album of the Year. (Photos: Geffen Records, Getty images)

When it comes to the 64th annual Grammy Awards, taking place this Sunday in Las Vegas, it will be a battle between Generation Z, led by 19-year-old singer-songwriter Olivia Rodrigo, and the Greatest Generation, represented by Tony Bennett. Old-guard icon Bennett, who recorded his final album Love for Sale with Lady Gaga while battling Alzheimer's disease and has since retired, will be a sentimental favorite. However, new-guard punk-pop star Rodrigo will likely benefit from changes made to the voting process (after the Weeknd’s shocking snub last year), which have made 2022’s ballot younger and hipper overall.

In fact, when Yahoo Entertainment spoke with Billboard’s awards editor and a veteran Grammys expert, Paul Grein, and broke down the “Big Four” categories — Record, Album, and Song of the Year, and Best New Artist — he predicted a clean sweep for Rodrigo. But we have many burning Grammy questions, and below, Grein has all the Grammy answers.

Yahoo Entertainment: Before we dive into the Big Four categories, obviously there were some big changes to the nomination process this year. There's been controversy regarding how the nominees have been chosen in the past, and a lot of that came to head with the whole Weeknd snub in 2021. Please explain the changes that were made, and how those changes may have affected who got nominated this year and how things might shake out.

Paul Grein: Well, the biggest change is that the Recording Academy discontinued nomination review committees across the board in all categories, including the Big Four categories that were previously determined by a committee of about 25 insiders. Now it's a straight vote by the voting members. I think the Grammys realized they should get out of the business of second- guessing their voters and just let the voters have the final say. And I think that was a positive change. I give [Recording Academy CEO] Harvey Mason Jr. a lot of credit for doing that.

How did the process work before this change?

The process was that the voters’ top 20 choices went to a committee, and that committee had the power take anything from the top 20 of the voters’ choices that they wanted. So, theoretically, they could bypass allof the voters’ top choices, and find other things that they like better from within that top 20 list. According to the Academy, the nominations review committee had no way of knowing what the voters had ranked first or 20th—v it was in alphabetical order, and they were kind of voting blind. But I should probably back up a bit here: The Grammys instituted nomination review committees start starting in 1989 in some of the subgenres, but they brought them into the Big Four categories, which are what most people focus on, in 1995. And the reason probably is that the year before, Tony Bennett had won Album of the Year for his MTV Unplugged album, and the Three Tenors’ live album was also nominated for Album of the Year. Meanwhile, no hip-hop or alternative albums were nominated for Album of the Year that year. And so, there were a lot of protests that the Grammys were out-of-touch with the most vital trends in pop music. The following year, Mike Green, who was then the president and CEO of the Recording Academy, instituted a nomination review committees to kind of oversee the voters — and sometimes second-guess the voters. It stood in place until this year. Interestingly, the very first year they don't have it, Tony Bennett is back with Love for Sale and could actually win again for Album of the Year!

Have there been any changes regarding who the Grammy voters are to make them less conservative, more diverse, younger, that sort of thing?

Yes. The Academy has worked very aggressively in the last five years to expand the membership and specifically to bring in more women, more voters of color. They have relaxed membership requirements and removed what some said were roadblocks to people being able to join. That’s one reason that the nominations have been gradually getting a little more contemporary.

Another change this year is the Recording Academy had already had expanded the Big Four categories from five to eight nominees in 2019, but now those categories each have 10 nominees, which is a lot! And it seemed like that was a last-minute decision…

It was a very last-minute decision. Harvey Mason Jr. acknowledged that the reason was there would've [otherwise] been no hip-hop, or very light hip-hop, representation in the Big Four categories. … But one thing to consider is with 10 nominees, theoretically something could win with just a little more than 10% of the vote. So, if a category is totally split, there could be some surprises.

OK, let's dive into all 40 the Big Four nominees, starting with Record of the Year. The nominees are “I Get a Kick Out of You” by Tony Bennett and Lady Gaga, “Drivers License” by Olivia Rodrigo, “Right on Time” by Brandi Carlile, “Kiss Me More” by Doja Cat featuring SZA, “I Still Have Faith in You” by ABBA, “Freedom” by Jon Batiste, “Peaches” by Justin Bieber featuring Daniel Caesar and Giveon, “Happier Than Ever” by Billie Eilish, “Montero (Call Me by Your Name)” by Lil Nas X, and “Leave the Door Open” by Silk Sonic. With the exception of Tony, ABBA, and Jon, this is quite a young-skewing category.

Yes, and there’s a possibility that that could work to Tony Bennett's advantage — that there is a solid block of older voters that has nowhere else to turn, and they'll all get behind him. He’s a great artist historically that everyone admires for staying in the game and staying relevant, and then there’s the intergenerational team-up with Lady Gaga and her kind of versatility to be able move among genres. There are a lot of strong things about it.

And of course, there’s the sentimentality factor. Tony is 95, and Love for Sale the last thing he’s ever going to do, due to his Alzheimer's. There won't be a dry eye in the house if he wins anything. It would be very emotional TV.

It could play into it a lot, and you make a good case. … But I should probably cut to the chase and say I think Olivia Rodrigo is likely to win all four Big Four awards. I have thought that “Drivers License” was the frontrunner for a Record and Song of the year since virtually the week it came out, in January of 2021, and nothing has changed my mind. I mean, it's a perfect Grammy record. It's very well-crafted. It has universal appeal. It's everything Grammy voters historically have liked. And of course, she'll win Best New Artist, too. The one category I think she's least sure of winning is Album of the Year, which I do think could go to Tony and Gaga.

Well, this is very interesting, because only two people have ever swept for the Big Four before. Christopher Cross first did it in 1981, and then it took three decade for someone else, Billie Eilish, to tie that record.

Yes, and this time it would only take two years — and again by a young woman, a teenager!

So, besides Olivia Rodrigo’s Sour and Tony Bennett and Lady Gaga’s Love for Sale, could anyone else win Album of the Year? The other eight nominees are Happier Than Ever by Billie Eilish, We Areby Jon Batiste, Justice by Justin Bieber, Planet Her by Doja Cat, Back of My Mind by H.E.R., Montero by Lil Nas X, Evermore by Taylor Swift, and Donda by Kanye West.

No, I think it'll be Olivia. Same for Song of the Year. It’s just such a strong song.

Olivia does seem like a lock for Best New Artist as well, but that is a very diverse and hip category. The other Best New Artist nominees are Arooj Aftab, Jimmie Allen, Baby Keem, Finneas, Glass Animals, Japanese Breakfast, the Kid Laroi, Arlo Parks, and Saweetie. Is there any chance that someone like Arooj could pull off an upset and be this year’s Esperanza Spalding?

That is a good point, actually! In 2010, everybody said, “Well, the one you can immediately write off is Esperanza; there's no way that she's going to win.” And she wound up winning Best New Artist. It was a reminder that you can't ever count anybody out — Esperanza Spalding was up against Justin, Bieber Drake, Florence + the Machine, and Mumford & Sons! There are still people who say, “How on Earth did that happen?” It's because the other four sort of split the more contemporary, commercial vote, and she had the jazz vote all to herself. But even as I'm trying to explain it, it's still kind of shocking.

Well, speaking of past Grammy shockers. … The big headline on Grammy nominations announcement day was that Jon Batiste surprisingly led the pack, with 11 nominations. So, is he going be this year's India.Arie and go home with nothing?

Ha! I mean, we all remember that [when India.Arie was 2002’s top nominee, but was completely shut out]. But the answer to your question is no. I don't think Jon will win any of the Big Four, and he's not going to win a big bundle of awards, but there are a few genre categories where he probably will win.

We haven’t really talked about Kanye West. He’s obviously a controversial figure at the Grammys this year, but he has always been a Grammy darling. How do his latest antics or Doja Cat’s, for that matter play into any chances of winning?

The most important thing we have to keep in mind when making predictions is that the voting concluded on Jan. 5. Voting was conducted between Dec. 6 and Jan. 5, and then because of the Omicron variant, the show was delayed from Jan. 31 to April 3. But voting closed almost three months ago, so we have to roll back to the beginning of the year — anything good, bad, or different that’s happened since then doesn't matter.

Do you think the Weeknd might actually ironically win this year, since he is nominated for three collaborations, with both Doja and Kanye? He’s up for Best Melodic Rap performance for Kanye West’s “Hurricane”…

“Hurricane” definitely has a shot. I doubt the Weeknd would show up, though. [laughs]

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