While working on my article about the biggest snubs of this year’s Grammy Awards nominations, it got me thinking about the multiple moments of the last two decades in the show’s history that have made me go “WTF”. And trust me, there were quite a few. But for the sake of brevity, I’m limiting this list to only ten.
Like many award shows, there are times The Grammys get it so right – Adele winning Best New Artist (BNA), Outkast winning Album of the Year (AOTY) for Speakerboxx/The Love Below (the last time a rap album won AOTY though certainly not the last time the genre deserved to win…more on that in a second) and other times when they get it so wrong that it just leaves you baffled.
As is always the case, let me be clear that these were moments that stood out for me. Naturally, I’m sure there are those who don’t think some of these moments were upsets or who felt other moments were bigger upsets. Fair enough.
And let me also add that I wasn’t necessarily angry or even disappointed by all of these moments. Some of these were just moments that based on various factors – biggest hit that year, critical acclaim, etc. – the winner was surprising and so yes, would be considered an upset. So without further ado, here are my top 10 Grammy Awards upsets of the last two decades.
1989 Beats To Pimp a Butterfly for Album of the Year – No, just no. And before any of the Swifties come with the argument of, “Taylor had five Billboard Top 10 hits from the album”, I will remind all that one Katy Perry had five Number 1 Billboard hits off her Teenage Dream album. The only artist to do so since Michael Jackson’s Thriller. And by my last count, Katy Perry not only did not win AOTY for Teenage Dream, she still doesn’t have a single Grammy Award. So let’s get that weak argument out of the way. And then the next go-to is of course, “1989 sold a lot…” Yes, yes it did. But if we were basing quality and awards only on what sold a lot, there would be some very questionable winners over the years. Popularity does not always equal good. That said, I want to be very clear that I believed then and still do that 1989 was a good pop album and it deserved to be nominated for Album of the Year. What it didn’t deserve, in my opinion, was to win. 1989 was a good, solid album – To Pimp a Butterfly was a masterpiece. Lyrically, thematically and musically, it was stellar and career-defining from beginning to end. There will never be any argument that will convince me this was the right call.
Maroon 5 Bests Kanye West for Best New Artist – This is one of the moments on this list that I wasn’t necessarily outraged about but would still categorize as an upset. To be clear, I was a fan of both Maroon 5 and Kanye West during their debut years. Songs About Jane still gets heavy rotation on my playlist. And in the interest of fairness, the album had significant commercial success, spawning multiple Billboard Top 20 hits. However, the critical and commercial response to The College Dropout was something significantly greater. That album positioned Kanye West as one of the most prolific and powerful voices in music.
Herbie Hancock Wins Album of the Year – This win would have been surprising if only because Jazz often gets slept on in the major categories. But what made it particularly shocking is that Hancock defeated both Amy Winehouse’s Back to Black and Kanye West’s Graduation. To say this one came out of left-field for many would be an understatement.
Steely Dan Upsets Eminem and Radiohead for Album of the Year – Much like Herbie Hancock’s win, this would have been a surprising win for many regardless. But what made it particularly shocking is that it came at the expense of some of the most critically acclaimed albums and artists of the year. Unlike some, despite being a fan of Eminem’s, I never thought he would win. There was too much controversy around him and the album at the time. Not to mention he was still a relatively new artist and award shows sometimes like for artists to “pay their dues.” But with Beck, Radiohead, and hell Paul Simon in the mix, Steely Dan is not the name I expected to be called that night.
Esperanza Spaulding Wins Best New Artist – I feel like no one was more surprised when Esperanza Spaulding’s name was called that night, than Esperanza herself. As previously noted, Jazz isn’t often shown much love in the major categories (unless you are a phenomenon called Norah Jones) and that fact in itself made Esperanza seemingly a longshot. But then you considered who she was up against that year, and it seemed all but impossible that she’d have any chance of winning – i.e. Justin Bieber, Drake, Florence and The Machine and Mumford & Sons (they would win Album of the Year just two years later). But win she did.
Eminem’s Recovery Loses Album of the Year – So remember that thing I said about artists paying their due? Well, Eminem’s comeback year with Recovery was supposed to be that. After a few years of personal and emotional upheavals owing to his addiction, Eminem got things back on track, channeling all he’d been through into his best album since The Eminem Show. Recovery was a commercial and critical smash. The media and industry were no longer screaming about boycotting his music and how evil and dangerous he was to impressionable youths. In short, Eminem had earned the respect of many and solidified his legacy. All that was missing was a win for Album of the Year – and, it didn’t happen.
John Mayer’s Daughters Wins Song of the Year – There is nothing inherently wrong with John’s Mayer’s Daughters. Albeit it’s a bit maudlin and sleepy. However, it’s not an all-around awful song. It just wasn’t in my opinion, the song of the year. Especially not when it was competing against Kanye West’s Jesus Walks and even Alicia Keys’ If I Ain’t Got You.
Kendrick Lamar is 0-7 at 2014 Grammy Awards – Yes, you read that correctly. For the 2014 Grammy Awards, Kendrick Lamar had seven nominations for his breakout debut album, Good Kid, M.A.A.D City, including Album of the Year and Best New Artist. He lost in every category. And the losses might not have been so disappointing, were it not for who he lost to, particularly in the Rap categories. Yes, I am, of course, referring to the saga of Macklemore & Lewis sweeping the Rap categories. Here’s the thing – much like Maroon 5 versus Kanye West, I’m not going to argue that Macklemore & Lewis had a stellar year and The Heist was a good album. Kendrick’s Good Kid, M.A.A.D City however, was better, which was a sentiment seemingly shared across the industry. And yet come Grammy night the votes went Macklemore & Lewis’ way.
Lose Yourself Loses Record & Song of the Year – Considered by many to be the best song of Eminem’s career, Lose Yourself was commercially and critically, an unquestionable smash. The song spent a whopping 12 weeks at the top of the Billboard charts and was certified diamond in sales (that’s 10 million records sold, for those who don’t know). Oh, and there was also that whole Academy Award for Best Original Song. And yet, come Grammy Awards 2004, it lost ROTY and SOTY to Clocks by Coldplay and Dance with My Father by Luther Vandross, respectively. And it’s no shade to either of these songs that are both perfectly fine. And of course, Dance with My Father had, at the time, the additional emotional punch of Luther Vandross’ having passed away prior to the song’s release. But the plain truth is neither of these songs was in any way as exceptional and well-crafted as Lose Yourself, and time and distance have only furthered this belief. Lose Yourself has aged like fine wine and still holds up almost twenty years later. Case in point, even former President Barack Obama is talking about how Lose Yourself was one of the songs that inspired him during his 2008 presidential run.
O Brother Where Art Thou Wins Album of the Year – A certain person is going to agree with this one. At the 2002 Grammy Awards, a quirky, bluegrass-inspired soundtrack, perfect for the Coen Brothers film of the same name, O Brother, Where Art Thou? won the award for Album of the Year. There was one major problem with this – many assumed and deservedly so, that U2’s All That You Can’t Leave Behind was the forgone winner. All That You Can’t Leave Behind was unquestionably U2’s best album since 1991’s Achtung Baby. Just the previous year, on the strength of the lead single, Beautiful Day, the band won both Song and Record of the Year. So it just seemed inevitable that the album was going to win Album of the Year. Alas, it was not to be.
PoPnOgR@PhY 