The 20 Most Baffling Grammy Award Winners of All Time

 

 

Here’s a look at the most outrageous Grammy Award winners in history, from 1959 through 2019.

 

Since the awards were first doled out in 1959, the Grammys have translated into little more than a rubbernecking exercise for millions of watchers baffled by what’s happened to popular music.

Now in its 62nd year, the annual presentation is a proverbial dumpster fire of clashing musical genres and a twisted assemblage of conflicting generational tastes.

The latest chapter of chaos combined with curiosity will be written on Sunday night, at 7 pm CST with the CBS live telecast of the Grammy Awards.

The mish-mash of generational rivalries, wandering attention spans, and awkwardly pigeon-holed acts crammed into misnamed categories have produced many inexplicable (and undeserving) winners.

What follows are my picks for the most outrageous Grammy Award winners of all time, along with my correct choice as to who should have won the award instead for that year.

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 (before his personal scandals). 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 is 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 saccharine 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 composer 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?).

(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 Dan. 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:

The Top/Bottom Ten

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(10) Milli Vanilli — “Best New Artist,” 1990

It’s easy to see a much clearer picture now, rather than 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 stripped away, and their careers mercifully ended, delighting those of us whose ears still painfully echo with the horrors of stolen music.  Using session musicians (and taking the credit) is problematic for any Grammy winner.  But committing fraud is another.  Good riddance.

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”)….or maybe not, since all the Beach Boys recordings were really done by The Wrecking Crew.

(8) Burl Ives (“Funny Way of Laughin”) — Best Country and Western Song, 1963

Burl Ives doesn’t get his historical due.  He 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 during the McCarthy era. 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 the iconic voice and life of George Jones, someone who would prove to be a giant influence 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 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.  Note:  This very well could be ranked #1 as the worst, most undeserved Grammy Award ever given, and if you doubt this, check out THIS VIDEO.

Who Should Have Won — The Clash

(6) “Most High” (Jimmy Page and Robert Plant) — Best Hard Rock Performance, 1999

Every rock n’ roll and blues fan reveres the 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 Led Zeppelin’s heyday from 1968-1978 by not giving them any awards, and then committed and 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 master songwriter and performer 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

How could voters ignore the Beatles masterpiece “Hey Jude,” which was easily the most deserving song of the year? A landmark achievement, the self-composed track 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 release only months later, known as The White Album. Oh, and then there were two other popular hit 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 simple sounded so amazing, as this live 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.  And besides, the song was recorded by not less than three singers, also released as a single by Patti Page and O. C. Smith on separate occasions that same year.  What makes the Bobby Russell version special?  Answer — nothing.  Russell didn’t even write the song!  Outrageous.

 What Should Have Won — “Hey Jude” (The Beatles)

(2) Jethro Tull — Best Hard Rock/Metal Performance, 1988

Jethro Tull….heavy metal?  Indeed.  British rock group Jethro Tull floored the audience and shocked the 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 dead President. All that’s remembered now is that this album should go down as the worst Grammy Award winner of all time.  Here’s the far better choice (here’s what a real singer sounds like without Autotune):

Who Should Have Won — I Left My Heart in San Francisco by Tony Bennett

 

Most Bizzare Five-Time Grammy Winner of All Time — Christopher Cross

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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 music maven won a whopping five Grammys in the year 1980 for his breakthrough debut album, which produced a quick flurry of hit singles. But his syrupy one-dimensional ballads ended up as pop music’s equivalent of pet rocks and beanie babies. In fairness to Cross, he didn’t fit the ideal profile of an MTV-friendly artist, an 80s-era detour, which was entirely based on appearances and superficiality. Within 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.

Meanwhile, 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.

READ MY COLUMN ON THE 2020 GRAMMY AWARDS HERE.