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):
And now, the worst, least-deserving, most outrageous ten winners of all time:
The Top/Bottom Ten
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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
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.
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
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
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
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
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.
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!”
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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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.