The Grammy Awards' Dumbest Decisions of the Past 30 Years

The Grammy Awards air tonight at 8, which means for about three hours on Twitter, the Grammy Awards will be relevant.

Otherwise, everyone knows they're a sham. They may look good on an artist's resume, mantle or ego, but after boosting sales for big winners for a week or two, the Grammys get tucked away in the recesses of our memories for the rest of the year.

As the supposed elite-defining monolith of the recording industry, the Grammy Awards are damned either way they do. The National Academy of Recording Arts and Sciences' tendency to recognize established vets too late for lesser works is maddening (Steely Dan's Two Against Nature won a slew of awards including Album of the Year in 2001; Herbie Hancock's River: The Joni Letters was named Album of the Year in 2008); the new development of recognizing less commercially visible but critically adored indie acts feels like a desperate attempt for coolness (Arcade Fire's The Suburbs won Album of the Year in 2011; Bon Iver was named Best New Artist last year).

That said, when Grammy gets it wrong, it gets it really wrong. Legends who've never won include Diana Ross, the Beach Boys, Bob Marley and Teddy Pendergrass (who, adding insult to injury, was the recipient of a half-hearted tribute by the illogically chosen Lady Antebellum in 2011). Milli Vanilli famously had their Best New Artist Grammy revoked in 1990 as a result of Fab Morvan and Rob Pilatus being exposed as frauds who did not sing on their records. The Grammys will never live that down, nor should they. Nor should Milli Vanilli's watery, weirdly sung and generic take on dance music have been recognized in the first place, even when people thought they were singing.

The Grammys must account for "quality" (whatever that means) as well as popularity (because the ceremony is a commercial endeavor in itself that is being packaged for consumption), and the Best New Artist category is where the two forces meet and explode into incomprehensibility. Supposedly, the Academy members who vote for these awards are urged to ignore sales figures and chart performance when determining their picks, but Best New Artist, in general is riddled with flavors of yestermonth, particularly of the teenybopper variety: the Backstreet Boys, the Jonas Brothers, Justin Bieber, Hanson, Avril Lavigne, Britney Spears, Kris Kross and Chris Brown have all been nominated in that category.

Tonight, Alabama Shakes, fun., Hunter Hayes, the Lumineers and Frank Ocean are all up for that trophy, and it generally takes years for us to gain some perspective on how off the mark the Grammys were (Hootie and the Blowfish won in 1996, which made sense then given their ubiquity but is almost unthinkable now). Looking back, the examples (in various categories) below strike me as egregiously out of touch, especially given the relevance of these artists in 2013. There are loads more examples — no one awards show can get everything right — these are just the ones that stick out from a particular pop fan's perspective:

  • In 1985' Lionel Richie's trifling Can't Slow Down won over classics like Prince and the Revolution's Purple Rain and Bruce Springsteen's Born in the USA. Cyndi Lauper's She's So Unusual and Tina Turner's Private Dancer were also nominated and still would have been better choices for their inventiveness.
  • Prince was honored for the first time in 1985 with some trophies (Best R&B Song for writing "I Feel for You," which was a hit for Chaka Khan that year and Best Rock Vocal Performance by a Duo or Group for the Purple Rain album), once in 1987 (Best R&B Vocal Performance by a Duo or Group - "Kiss") and then not again until 2005 for Musicology's "Call My Name" (Best R&B Vocal Performance - Male). This means his double-album masterwork, 1987's Sign "O" the Times, won nothing.
  • Timbaland, who helped shape '90s hip-hop and R&B much like Prince did for R&B and pop in the '80s, didn't win anything until 2007 for Justin Timberlake's "Sexyback," a conventional song by the forward-thinking standards he'd set over a decade before.
  • 1989's Record and Song of the Year went to Bobby McFerrin's "Don't Worry Be Happy," a T-shirt slogan of a song that has aged as well as a beer koozie that says, "Is that your final answer?" It beat Anita Baker's "Giving You The Best That I Got," Steve Winwood's "Roll With It, " Tracy Chapman's "Fast Car" and Michael Jackson's "Man In The Mirror."
  • 1989's Best R&B Vocal Performance - Male went to temp it boy Terence Trent D'Arby for his Introducing The Hardline According To... Terence Trent D'Arby album. It beat Al B. Sure!'s "Nite And Day," Luther Vandross' Any Love Stevie Wonder's Characters and Teddy Pendergrass' Joy. As mentioned before, Teddy Pendergrass never won and it's all Terence Trent D'Arby's fault.
  • 1989 marked the inaugural Best Rap Performance Grammy, which went to DJ Jazzy Jeff & the Fresh Prince's "Parents Just Don't Understand." I get it: It was narrative, easy to grasp and, ironically, family friendly. The four songs that it beat out — J.J. Fad's "Supersonic," Kool Moe Dee's "Wild, Wild West," LL Cool J's "Going Back To Cali" and Salt-n-Pepa's "Push It" — would play infinitely better at any party today, though.
  • The next year, Young MC's "Bust a Move" won in that category. It was a better choice than other nominees D.J. Jazzy Jeff & The Fresh's "I Think I Can Beat Mike Tyson" and Tone Loc's "Funky Cold Medina," but lightweight pop compared to the bona fide classics it shared the slate with: Public Enemy's "Fight The Power" and De La Soul's "Me Myself & I."
  • In 1990, Paula Abdul was nominated for Best Pop Vocal Performance ("Straight Up").
  • In 1991, easy listening, pseudo-inspirational sentimentality beat out gut-wrenching sentimentality: Phil Collins' "Another Day in Paradise" nabbed Record of the Year and Bette Midler's "From a Distance" was named Song of the Year; both shut out Sinead O'Connor's cover of Prince's "Nothing Compares 2 U."
  • 1992's Best New Artist was Mark Cohn. Who, right? Well, the rest of the nominees list is a who's who of 90's cheese (some more enduring and talented than others): Boyz II Men, C+C Music Factory, Color Me Badd and Seal.
  • In 1993, Eric Clapton's excruciating "Tears in Heaven" was named Song and Record of the year.
  • If Eric Clapton's ode to his dead son appealed to the Grammys' sensitivity, his trendy musical strip down appealed to its adoration of "authenticity": His Unplugged release was named Album of the Year. Three years later, Tony Bennett would also win that trophy for his Unplugged album.
  • In 1993, Mary J. Blige's What's the 411?, the enormously influential album that converted the sound of R&B into hip-hop soul, didn't receive a single nomination.
  • In 1997, Celine Dion won Album of the Year for Falling Into You. She beat Beck's Odelay, the Fugees' The Score, Smashing Pumpkins' Mellon Collie And The Infinite Sadness and the Waiting To Exhale soundtrack.
  • In 1998, Shawn Colvin, who had released four albums at that point, was named Best New Artist. She beat people who'd stick around much longer and do way more interesting things with their careers: Erykah Badu, Fiona Apple and Sean "Diddy" Combs. She also beat Hanson.
  • That's not a Combs endorsement, though — that such a deficient MC's No Way Out won Best Rap Album that year over Missy Elliott's Supa Dupa Fly, The Notorious B.I.G.'s Life After Death and Wu-Tang Clan's Wu-Tang Forever is a joke. Wyclef Jean's The Carnival was also nominated.
  • In 2001 Macy Gray won Best Pop Vocal Performance for her nails-in-a-blender rendition of "I Try."
  • In 2003, Norah Jones swept, winning all seven trophies for which she was nominated, including the three biggest categories (Album/Song/Record of the Year) and Best New Artist. Now you sometimes hear her at weddings.
  • In 2006, Kelly Clarkson's "Since U Been Gone," as universally loved as a pop song got in the 00s, was not nominated for Song or Record of the year. It did, however, win Best Pop Vocal Performance - Female.
  • In 2012, Kanye West's daring and gorgeous My Beautiful Dark Twisted Fantasy failed to score a nomination for Album of the Year (it did win the award for Best Rap Album, though). Adele's nice and safe 21, though, cleaned up.
  • In 2012, Chris Brown won Best R&B Album for his mostly god-awful F.A.M.E. album. That is the single most invalidating piece of evidence against the Grammys since Milli Vanili, no exaggeration.

[Image via AP]