Lionel Richie Beats Prince, Bruce Springsteen, Tina Turner and Cyndi Lauper for Album of the Year (1985)
To be clear: there’s absolutely nothing wrong with Lionel Richie’s Can’t Slow Down, which won the Grammy for Album of the Year in 1985. You can’t say it doesn’t have bangers: “Hello” is still a classic, and “All Night Long (All Night)” is almost certainly being played at a wedding reception or cruise ship mixer at exactly the moment you’re reading this. The album was a slick, diamond-selling chart-topper, and a prime example of an R&B veteran upping his studio game in the immediate aftermath of Thriller. It must have seemed the safe choice. But good god, look at who Richie’s four fellow nominees were. Most obviously, Purple Rain was the type of lightning-in-a-bottle album that transforms a star into a supernova, turning Prince from a popular R&B figure into the kind of generational icon who could subsequently spend years releasing jazz fusion experiments and change his name to an unpronounceable symbol and still sell out stadiums anytime he wanted to. Bruce Springsteen’s Born in the U.S.A. was similarly transformative, establishing Bruce as the decade's rock standard-bearer. Tina Turner’s Private Dancer was the sort of comeback triumph that Grammy voters usually swoon over, cementing the Queen of Rock 'n' Roll's solo superstar status after finally breaking free of Ike's abusive clutches. And though it might have seemed a comparably minor work at the time, history has been extraordinarily kind to Cyndi Lauper’s She’s So Unusual, which now stands as a blueprint for so many of the left-of-center pop stars who followed in her wake, and contained a signature track so undeniable that even Miles Davis took to covering it. The Grammys had a four in five chance to look way ahead of their time with this field, and they took the one option that feels very, very of its time instead. -- Andrew Barker
Jethro Tull Beats Metallica for Hard Rock/Metal Performance (1989)
Second-guessing the Grammy Awards has long been one of America’s favorite pastimes. However, when Alice Cooper opened the envelope at the 31st Grammy Awards to announce the inaugural winner for Best Hard Rock/Metal Performance Vocal or Instrumental, literally no one expected the words “Jethro Tull” to come out. Amidst the stunned audience reaction, Cooper, who appeared to take a beat, accepted the award for the absent band. There was no clapping. No cheering. Backstage, numerous musicians and industry people were at a loss. Metallica, who had performed and appeared to be the shoo-in, took it in grace. Jethro Tull's Ian Anderson didn’t think anything of it when the phone call arrived. The Academy promptly split the two categories and Metallica won the following year in the Best Metal Performance category for "One." -- Amy Hughes
Macklemore Beats Kendrick Lamar for Best Rap Album (2014)
It’s hard not to feel a little bad for Macklemore, who apparently knew as well as anyone that his album with Ryan Lewis, The Heist, probably didn’t deserve to win the Best Rap Album Grammy in 2014 over future Pulitzer Prize-winner Kendrick Lamar’s landmark major label debut, Good Kid, M.A.A.D. City. In fact, he was so aware of this that he told Lamar as much in a text message, writing: "You got robbed. I wanted you to win. You should have." It was a nice gesture, though subsequently sharing that text in a social media post certainly left him open to accusations of doing a little too much. Nonetheless, it was hardly his fault that Grammy voters missed the boat by a mile here (the two also beat Lamar for Best New Artist later that same night), and Lamar has since claimed the award in this category for each of the next three years he’s been eligible. -- A.B.
Diana Ross’ Lifetime Shutout (1965-Present)
Every year around this time, someone will usually circulate a list of the major artists who have never won a competitive Grammy, and that list will always contain a solid dozen head-scratchers. (Tupac, ABBA, Jimi Hendrix, Bjork, Bob Marley…) But generally speaking, you can usually understand why most of those artists are Grammy-less: some had tragically short careers, some were a bit too controversial for skittish voters in their heyday, and some left the sort of influence on future generations that was only obvious in retrospect. But Diana Ross? Seriously? The very model of the modern R&B diva, Ross enjoyed several decades on top, both as a Supreme and as a solo artist, and the Recording Academy has had more than enough chances to properly honor her. Nominated for the first time way back in 1965 for the Supremes’ “Baby Love,” she racked up another dozen Grammy nominations throughout the ‘60s, ’70 and ‘80s, always falling short of the gold. She was finally given a Grammy Lifetime Achievement Award in 2012, and then another one for good measure in 2023, but that hardly makes up for a full half-century of cold shoulders for one of the 20th century’s defining pop stars. -- A.B.
Steely Dan Beats Radiohead, Eminem for Album of the Year (2001)
Speaking of trying to make good on past omissions, Grammy voters have a long history of issuing de facto makeup awards, in which respectable late-career efforts from veterans serve as useful stand-ins for their previously under-awarded bodies of work. Bob Dylan, Ray Charles, Robert Plant, Santana, Luther Vandross — all received their first major category Grammys late in the game (or in Charles’ and Vandross' cases, after their deaths), and, well, better late than never. The only trouble with this, however, is that by playing catch-up, the Grammys can miss the opportunity to do right by contemporary artists the first time around. Such was the case in 2001, when Steely Dan (repeat nominees during their unimpeachable 1970s run, though never winners) took Album of the Year for comeback effort Two Against Nature, their first new album in two decades. It was a decent record! And Steely Dan absolutely should be Grammy winners. But also nominated in the category that year: Radiohead’s playbook-ripping Kid A, now widely considered one of the most influential rock recordings of the current century, and The Marshall Mathers LP from Eminem, then the most controversial and talked-about recording artist on earth. Neither Eminem nor Radiohead have yet won a Grammy in one of the major four categories; check back in around 2034 or so. -- A.B.
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Hip-Hop, in General (1973-Present)
It took the Grammys a few years before its voters fully took to rock and roll, although the first rock Album of the Year winner has certainly held up pretty well. But the institution took much longer to wrap its head around rap, and the Grammys’ relationship with the hip-hop community remains somewhat fractious to this day. Hip-hop was well over a decade old when the first rap category was introduced in 1989, and the inaugural award was boycotted by several nominated rappers when they learned it would not be televised. Early genre category winners tended to skew safer and poppier, with the likes of Young MC, MC Hammer, DJ Jazzy Jeff & the Fresh Prince and Sir Mix-a-Lot winning most of the first hip-hop Grammys, while far more cutting-edge artists like Public Enemy, De La Soul, Eric B & Rakim and N.W.A were left empty-handed (or in the case of the latter two, never nominated). And even once Grammy voters started to get a better handle on rap in the genre categories, the “big four” general field categories continued to be problematic. To date, only two hip-hop or hip-hop-adjacent acts have won Album of the Year (Lauryn Hill’s The Miseducation of Lauryn Hill and Outkast’s Speakerboxxx/The Love Below), and it wasn’t until 2019 that a hip-hop song won for Record or Song of the Year (Childish Gambino’s “This Is America” was the first for both). Every few years, it seems, a major hip-hop artist will decide they've had enough and swear off participating in the Grammys all together, and it's hard to blame them. -- A.B.
The Starland Vocal Band Wins Best New Artist (1977)
For as often as the Grammy Awards have gotten it wrong with their trophies, they haven’t always gotten it that wrong with the category of Best New Artist. Indeed, in many cases, the winners in that particular category have continued onward to long and storied careers..like, say, a little band from Liverpool called the Beatles. But few bands are quite so much in the category of "Not the Beatles” as the 1977 winners, the Starland Vocal Band. Best known for their hit single “Afternoon Delight,” an unabashed ode to daytime canoodling so cheesy that it was covered by Ron Burgundy and the Channel 4 News Team for the Anchorman soundtrack. Okay, fine, so the song has its merits. But when you consider that the award could’ve gone to Boston or the Brothers Johnson – or, more disconcertingly, that Blondie, the Ramones, the Runaways, and even the Alan Parsons Project weren’t nominated – it’s rightfully gone down in history as a key moment in demonstrating the woeful unhipness of Grammy voters. (See also: the following year, when Debby Boone won the award.) -- A.H.