The Most Baffling Grammy Award Winners of All Time
Let the countdown begin, from 20 down to 1, with the most baffling Grammy Award winners of all time plus the reasons why it’s an outrage these artists and songs were selected — and who should have won.
To say the Grammy Awards have been reduced to a guilty pleasure would be an understatement.
Since these awards were first doled out in 1959, the Grammys have always translated into little more than a rubbernecking occasion for dedicated listeners and lovers of music. Now in its 57th year, the annual presentation is a proverbial car crash of clashing musical genres and a twisted assemblage of conflicting generational tastes.
Seriously, what’s measured or achieved when pitting Arcade Fire, Eminem, Lady Antebellum, Lady Gaga, and Katy Perry against one other, tossed and blended into the same melodic gumbo, as occurred in 2011 when these were the five nominees in the “Album of the Year” category? Aren’t most of the rockers going to vote for the rock group? Won’t all the rappers instinctively vote for the rap artist? Isn’t the country singer going to attract the votes from those connected to country music? What’s the whole point of it all, other than an extended time buy on a major television network and a three-hour commercial for additional sales and airplay?
The Grammy Awards are a popularity contest among aging music industry insiders, many of them completely clueless as to conventional tastes and new trends. Simple as that. Winning partially depends on a couple of things —  Luck of the draw (two artists with a crossover following unlucky enough to nominated within a single category often cancel each other out), and  Overall name recognition and familiarity. For this reason, many past winners have been artists well past the primes of their careers — from Bob Dylan (1998) to Ray Charles (2005) to U-2 (2006).
Indeed, over the years the mish-mash of generational rivalries, wandering attention spans, and awkwardly pigeon-holed acts have produced some truly baffling, and most undeserving winners. What follows are my picks for the most outrageous Grammy Award winners of all time, along with my proper choices as to who should have won the award instead for that year and musical category. Let’s call this my “Anti-Grammys.” I’ve tried to not let my own musical tastes and biases influence the selections too much, although admittedly, there’s lots more rock and pop music discussion than is warranted given the wide variety of music that’s been recognized at the Grammys. I wish there were more jazz, classical, and alternative subjects for discussion when it comes to the presentation.
Now, let the countdown begin, from 20 down to 1, with progressively more background discussion and the reasons why these artists and songs were selected. I’ve also included a special “lifetime achievement” category reserved for the very worst Grammy winner of all time and the most outlandish year ever for the Grammys. That comes at the conclusion of my list:
Dishonorable Mention (11-20):
(20) “Moon River,” by Henry Mancini winning “Record of the Year” in 1962, instead of The Dave Brubeck Group for “Take Five.” Mancini was a wonderful composer and “Moon River” became a huge hit as the accompanying soundtrack to the movie “Breakfast at Tiffany’s.” But “Take Five” stood the test of time far better and it remains one of the best jazz recordings ever.
(19) “Use Somebody,” by Kings of Leon winning “Record of the Year” in 2010, instead of Lady Gaga for “Poker Face.” It’s not that “Use Somebody” isn’t a well-executed and deserving song. It’s just that Lady Gaga’s exemplary effort was far more innovative and globally infectious — both then and now.
(18) “Don’t Worry, Be Happy,” by Bobby McFerrin winning “Record of the Year in 1989, instead of Michael Jackson for “Man in the Mirror.” Somehow, an annoying bubble-gum song with a terrible message (don’t worry, be happy? really? seriously?) topped the far more serious and deserving monster hit by one of the greatest artists in pop history. The only explanation for this egregious mistake was that voters must have been suffering from Michael Jackson fatigue, as he pretty much dominated the 1980s music scene and by then some rivals were bitterly tired of him.
(17) “River: The Joni Letters,” by Herbie Hancock winning “Album of the Year” in 2008, instead of Amy Winehouse for “Back to Black.” For more than three decades, Hancock has given the world a lot of great music. But this was far from his best career effort. Winehouse was the edgier, far more interesting, crossover-pick for her throwback R&B style and extraordinary vocal interpretations on what remains a flawless album (one of my favorite compositions of the last ten years).
(16) “You Light Up My Life,” by Debby Boone winning “Song of the Year” in 1978, instead of “Evergreen” performed by Barbra Streisand and composed by Paul Williams, which was the only tie-in Grammy history. Boone’s embarrassingly cheesy ballad now comes across little more than a wide-lapelled polka-dotted fashion statement and a throwback to a gutless period in popular music dominated by coked-up disco queens and the vanilla sound of Barry Manilow. It’s hard to believe nominees The Eagles, Carly Simon, and Glen Campbell all lost to this sappy feather-haired nobody. My two choices would have been either Stevie Wonder (“Sir Duke“) or the brilliantly-composed “Star Wars” theme, by the great John Williams.
(15) “Games People Play” by Joe South winning “Song of the Year” in 1970, instead of anything else from the rich catalog of popular music recorded and released not just within the rock genre, but the golden era of Motown, as well. Even prolific composer Burt Bachrach, who had two nominations in this category (canceling each other out, most likely) was a far more deserving choice. Has anyone ever heard of Joe South since he walked on stage that night, beating out Diana Ross, The Beatles, The Rolling Stones, The Jackson 5, Neil Diamond, and B.B. King (“The Thrill is Gone” was eligible that year — how did that not win?). This is like picking Roseanne Barr in a Miss America pageant.
(14) “Roseanna,” by Toto winning “Record of the Year” in 1983, instead of Willie Nelson for “Always on My Mind.” What an awful song and a regrettable pick. A disgrace. An embarrassment. Disreputable. Utterly baffling. Insane. Voters much have been smoking some of Willie Nelson’s weed. “Every Breath You Take” by the Police, “Sweet Dreams” by The Eurythmics, and “Beat It” by Michael Jackson all came out that year. “Roseanna” won over those songs? How?
(13) “Two Against Nature,” by Steely Dan winning “Album of the Year” in 2000, instead of anything else released that year. Give it to Radiohead, Eminem, Paul Simon, or Beck — all who were nominated and then bypassed for the best album that year. Not Steely fucking Dan. What next? If Steely Dan can win a Grammy, then there’s hope for Adam Sandler winning an Oscar. My picks would have been Garth Brooks’s live double album or Christina Aguilera’s self-titled debut best-seller.
(12) Hootie and the Blowfish winning “Best New Artist” in 1996, instead of either Alanis Morrissette or Shania Twain. No brainer. Enough said. No excuse for this oversight. Even at the time, anyone could see Morrissette and Twain’s natural talent and staying power as potentially volcanic forces in popular music. Not Hootie. Not the Blowfish.
(11) “Kiss from a Rose,” by Seal winning “Record of the Year” in 1996 instead of TLC’s “Waterfalls.” TLC was a wonderfully gifted R&B girl group, and this was their biggest crossover hit. But that didn’t matter. Seal’s overwrought and melodramatic torture of a song “Kiss from a Rose” won, mostly because the flop from two years earlier got remixed into the “Batman” movie soundtrack, and then quickly shot up the charts. That wasn’t even Seal’s best song released from that epic album. “Prayer for the Dying” was. Listen to the two songs. It’s no contest.
And now, the worst, least-deserving, most outrageous ten winners of all time:
(10) Milli Vanilli — “Best New Artist,” 1990
It’s easy to see a much clearer picture now, rather than way back then, when these two pop music Grammy winners from Germany faked and lip-synched their way to a scandalous victory. Fortunately, their careers ended up on the ash heap of music history, which gives us all hope that the same fate could ultimately befall all the Autotune frauds and phonies. Milli Vanilli was exposed and discredited, their Grammy award was ripped away, and their careers mercifully ended, delighting those of us whose ears still painfully echo with the horrors of their awful music.
Who Should Have Won — Indigo Girls
(9) “Winchester Cathedral” (The New Vaudeville Band) — Best Contemporary Song, 1966
In an astonishing year in music that produced timeless classics including — Born Free, California Dreamin’, Summer in the City, Strangers in the Night, Wild Thing, Good Vibrations, I’m So Lonesome I Could Cry, The Sound of Silence, Homeward Bound, Wipeout, Land of 1,000 Dances, If I Were a Carpenter, Zorba the Greek, and Yesterday (this is only a partial list!) — guess what song ended up winning the “Best Contemporary Song” Grammy that year? Answer — “Winchester Cathedral” by those rock legends, The New Vaudeville Band. Urgh!
Who Should Have Won — The Beach Boys (“Good Vibrations”)
(8) Burl Ives (“Funny Way of Laughin”) — Best Country and Western Song, 1963
Burl Ives was a multi-talented songwriter, musician, and actor, one of the few to be nominated for both an Oscar and Grammy. He performed folk songs, played villains in movies, did voiceovers, and was even blacklisted. Yet, he is perhaps best known today for his iconic song and self-portrayal in the annual “Rudolph the Red-Nosed Reindeer” television program shown every Christmas season. Ives won a Grammy in 1963 for a song that’s since been forgotten, which wasn’t even a country song, edging out George Jones, someone who would prove to be an icon in country music for the next five decades. Jones, then a breakout artist with one of his very first hit recordings, deserved the Grammy.
Who Should Have Won — “She Still Thinks I Can,” By George Jones
(7) Starland Vocal Band — Best New Artist, 1977
Look up the Starland Vocal Band sometime, if you want a good laugh. The group recorded had one lame hit, the wickedly torturous “Afternoon Delight,” the epitome of a musical bologna sandwich and a fitting soundtrack for the decline of Western civilization. Even the mediocre rock group Boston, which was nominated in this category, lost to the trifling trio. This was a very bad year for popular music, arguably the worst ever as rock was phasing into disco and (later) new wave. And punk was still considered an oddity, if not outright musical anarchy.
Who Should Have Won — The Clash
(6) “Most High” (Jimmy Page and Robert Plant) — Best Hard Rock Performance, 1999
Everyone who loves rock n’ roll and the blues reveres the classic music of Led Zeppelin. That said, this was one of the two frontmen’s weakest efforts, no doubt brought about by the opportunity of a potentially lucrative reunion album and tour, however brief that lasted. Meanwhile, Marilyn Manson, Metallica, Pearl Jam, and Kiss were each overlooked by voters in this category. The Grammy voters got it wrong in the Zeppelin’s heyday from 1968-1978 by not giving them any awards and then committed an even more atrocious act by bestowing upon them what amounts to an apology award more than two decades later, long after their musical and cultural relevance was over.
Who Should Have Won — “The Dope Show,” by Marilyn Manson
(5) Eric Clapton (“Layla”) — Song of the Year, 1992
It’s painful to include legendary Eric Clapton on any “undeserving list.” He’s one of the greatest guitarists in popular music in history and probably deserves far more official accolades. But his 1992 Grammy win for a re-worked acoustical version of a song initially recorded in 1970 made no sense whatsoever, especially given the force the musical force that Nirvana was at the time. The song that should have won instead defined a new sound and an entire generation and continues to receive praise as one of the most innovative rock songs ever recorded. It’s on virtually every “greatest” list of songs.
Who Should Have Won — “Smells Like Teen Spirit” (Nirvana)
(4) A Taste of Honey — Best New Artist, 1978
Disco was certainly king during the late 70s, and this honor was a mirrored ball tossed to a manufactured cookie-cutter musical group that ultimately became a one-hit-wonder, with that timeless classic “Boogie Oogie Oogie.” Don’t worry, you’re not alone. I don’t know it either. A Taste of Honey disbanded soon thereafter and would be a historical footnote were it not for their mystifying victory as the music industry’s “Best New Artist” in a year with far better nominees.
Who Should Have Won — Elvis Costello
(3) Bobby Russell (“Little Green Apples”) — Song of the Year, 1969
What! How in the hell could The Beatles masterpiece “Hey Jude,” not be the song of the year? A landmark achievement, the song was the first single ever released on Apple Records and was recorded in the summer of ’68 following the group’s return from three-months in India. That turned out to be a gargantuan year for the Fab Four, with several hits coming off the Magical Mystery Tour sessions, followed by the stellar double-disc just months later, known as The White Album. Oh, and then there were two other popular singles, “Revolution” and “Lady Madonna.” Breaking with tradition, “Hey Jude” wasn’t even included on any album collection (until after the group’s final breakup in 1970). The song spent a staggering nine weeks at number one, then a record — this in the midst of an explosive era when society was rapidly changing, racial and cultural barriers were coming down, and so much extraordinary music was being recorded — from rock n’ roll to Motown. “Hey Jude” shattered conventional formulaic radio-friendly thinking at the time, clocking in at more than 7 minutes. What begins as a slow piano-laden ballad with a single voice becomes an orchestral tour-d-force, finishing off with the memorable sing-a-long, “na, na, na — na, na, na, na.” Never has anything so ridiculously simple sounded so amazing, as this raw appearance in the U.K. on The David Frost Show reveals:
So, what won that year, instead? Chew on this. Bobby Russell’s mostly forgettable sleepy lullaby “Little Green Apples,” performed by O.C. Smith. Remember that one? I didn’t either. So, I had to look it up. Here’s the “Song of the Year” winner for what was arguably the greatest year of popular music in history:
What Should Have Won — “Hey Jude” (The Beatles)
(2) Jethro Tull — Best Hard Rock/Metal Performance, 1988
British rock group Jethro Tull floored the audience and shocked the entire music world in 1988, winning a Grammy in a category they had no business even being nominated in. The flute-infused rock act dusted off cobwebs from the early 1970s by winning the “Best Hard Rock/Metal Performance” honor, kicking far more deserving Metallica off to the curb. This incomprehensible oversight caused a major shakeup in the way musical genres were classified from that point forward. Two years later, Metallica, which was at the height of their creative peak, did indeed win a Grammy. The metal group took to the stage and famously quipped, “First thing we’re going to do is tank Jethro Tull for not putting out an album this year.”
Who Should Have Won — Metallica
(1) Vaughn Meader (The First Family) — Album of the Year, 1963
Chances are, you’ve never heard of this artist or this mostly-forgotten album, which inexplicably won “Album of the Year” in 1963. In fact, this became one of the fastest-selling albums of all time and racked up with more than 7 million total records sold. Vaughn Meader’s entire act consisted of doing his impression of President John F. Kennedy, lampooning the famous Kennedy mystique, and mocking political events of the day. The first family reportedly hated it, which probably drove up sales even higher due mostly to curiosity. Strangely, way back then “Album of the Year” wasn’t just reserved for music. Comedy was also eligible for consideration (recall Bob Newhart’s landmark win in this category in 1961, which was probably well deserved). However, Vaughn’s off-the-wall album wasn’t even the best comedy performance of the year. That title most certainly should have gone to Lenny Bruce, then at the height of his popularity and in the news constantly at the subject of major controversy. Meanwhile, Vaughn Meader’s one-trick-pony career went into the tank after the terrible events of November 1963, since no one wanted to laugh anymore about the dead President. All that’s remembered now is that this album should go down as the worst Grammy Award winner of all time.
Who Should Have Won — “I Left My Heart In San Francisco” by Tony Bennett
SPECIAL RECOGNITION: WORST GRAMMY AWARD WINNER OF ALL TIME (LIFETIME ACHIEVEMENT)
Winner — Christopher Cross
Guess who has more Grammy Awards than The Beach Boys, Chuck Berry, The Doors, Jimi Hendrix, Janis Joplin, Bob Marley, Diana Ross, Led Zeppelin, Queen, The Who, or Tupac Shakur — combined?
Answer — Christopher Cross. This milquetoast talent won a whopping five Grammys way back in 1980 for his breakthrough debut album, which produced a slew of hit songs. But his syrupy one-dimensional ballads ended up as the musical equivalent of pet rocks and beanie babies. Also, in fairness to Cross, he didn’t exactly fit the ideal profile of an MTV-friendly artist, which was largely based on appearances and superficiality. Within only a few years of a smashing debut and five fuddled acceptance speeches at that year’s Grammys, Cross had all but disappeared from the charts. His last Billboard appearance was way back in 1985.
By the way, The Beach Boys, Chuck Berry, The Doors, Jimi Hendrix, Janis Joplin, Bob Marley, Diana Ross, Led Zeppelin, Queen, The Who, and Tupac Shakur have never won a Grammy Award. But Christopher Cross has five. That pretty much sums up the travesty of this annual spectacle.
READ MORE: Matt Lessinger’s annual Grammy Awards picks for 2015. CLICK HERE