The 14 Most Shocking Former Grammy Winners Ever

Winning your first Grammy is a huge accomplishment for any music artist, with big stars like Beyoncé, Adele, Taylor Swift and Billie Eilish all picking up multiple awards in the early stages of their careers.

However, in addition to coveted titles like Album and Record Of The Year, the Grammys also feature a lot of unusual and special categories – meaning there have been some surprising and unexpected recipients over the years.

Here are 14 of the most surprising and unexpected Grammy winners of the past…

Barack Obama

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Yes, let’s start with the big one, shall we?

Barack Obama is actually a two-time Grammy winner, picking up both awards before being elected US President.

His two Grammy wins were in the Best Spoken Word Album category, for the audiobook versions of his Dreams From My Father and The Audacity Of Hope.

In 2020, Michelle Obama also won her first Grammy, again for the audiobook version of her memoir, Becoming.

Bill Clinton, Mikhail Gorbachev, and Sophia Loren

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JLN Photography/Action Press/Lorenzo Carnero/Zuma Wire/REX/Shutterstock/

Not only were these three Grammy winners unlikely to perform as individuals, what’s even more incredible was that they won as a trio.

The former US President, the leader of the Soviet Union and the screen legend collaborated on a record combining Peter And The Wolf and Wolf Tracks, earning the award for Best Spoken Word Album for Children in 2004.

Carrie Fisher

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Chris Jackson/Getty Images

Carrie Fisher earned a posthumous Grammy in 2018, again in the Best Spoken Word album category, for the audiobook version of her memoir, The Princess Diarist.

The Star Wars legend was previously nominated for the same award in 2010, but lost to Michael J Fox’s Always Looking Up.

Baha Men

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If you’re having trouble figuring out the origin of the name “Baha Men,” perhaps the phrase “who let the dogs out” will ring a bell.

Although their signature song was the most divisive, it was named Best Dance Recording in 2001.

Jonze spike

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Rich Polk/Getty Images for Capitol Music Group

You may know Spike as the man behind thought-provoking films like Being John Malkovich and the romantic comedy Her, or the big screen adaptation of Where The Wild Things Are.

However, he also has a number of impressive music videos, including Björk’s It’s Oh So Quiet, Weezer’s Buddy Holly, and Fatboy Slim’s Weapon of Choice, which earned him a Best Music Video Grammy in 2002.

Kathy Griffin

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After completing her well-documented mission to win an Emmy for her reality show My Life On The D-List, Kathy Griffin set out on a new mission to bag the Grammy for Best Comedy Album.

It took six years (the first special he sent out was literally called For Your Consideration), but he finally did it in 2013, with his comedy album Calm Down Gurrl.

Honestly, he should also win something for his iconic talk show theme song.

Kate Winslet

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VALERIE MACON/AFP via Getty Images

The Titanic star’s awards cabinet isn’t exactly barren, with one Oscar, three Baftas, one Emmy and four Golden Globes to her name.

In 2000, he could also boast of being a Grammy winner. Unfortunately, it wasn’t a win for her too-often overlooked single, What If, but rather a win in the Best Spoken Word Album For Kids category.

Coincidentally, Kate is now just one Tony Award away from achieving EGOT status, something that hasn’t escaped her attention either.

Viola Davis

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VALERIE MACON via Getty Images

And while we’re on the subject of EGOTs, Viola Davis achieved this legendary status in 2023, when she earned her first Grammy.

Unfortunately, it’s not for any musical (although there’s still plenty of time for that!), but rather the audiobook version of her memoir Finding Me.

White Betty

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Vincent Sandoval/WireImage

After more than 70 years in the entertainment industry, the late, great Betty White was finally able to call herself a Grammy winner in 2012.

He received the award for the audiobook version of his memoir If You Ask Me (And Of Course You Won’t).

Zach Braff

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Carlo Allegri via Getty Images

In 2005, the Scrubs alum won a Grammy for the soundtrack accompanying his directorial debut, Garden State.

The compilation – produced by Zach himself – features all the mid-2000s mainstays you’d expect, including Coldplay, The Shins and, of course, Frou Frou’s Let Go, which will once again be used on the big screen in the Christmas romance – com Vacation a year later.

The Muppets

The Muppets

The Muppets deserve all the accolades, if we’re honest, so we’re happy to say that they’ve received several Grammys over the years, first winning Best Recording For Children for their Muppet Show album in 1978. They went on to took home the same award the following year for The Muppet Movie soundtrack.

Nearly 30 years later, they triumphed in the same category for their festive offering Green And Red Christmas.

Their obscure colleagues on Sesame Street can also boast multiple Grammys to their name, most recently for their 2001 album Elmo And The Orchestra.

Martin Luther King Jr

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It’s perhaps no surprise that Martin Luther King Jr’s Grammy win was in the Best Spoken Word category, for his recording of his Why I Oppose the War in Vietnam speech.

What was perhaps more surprising was the fact that he had actually been nominated twice before, only losing one year earlier for the audio recording of his world-famous I Have A Dream speech.

Steve Jobs

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Ryan Anson/AFP via Getty Images

Following his death in 2011, the late Apple co-founder was awarded a posthumous honorary Grammy.

He is credited with changing the way we consume and listen to music, thanks to products like the iPod and the iTunes store.

Alvin and the Chipmunks

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Albert L. Ortega via Getty Images

The singing rodents actually have six Grammy wins to their name.

These included Best Comedy Performance for The Chipmunk Song in 1959 (which oddly, was even nominated for Record Of The Year at the same ceremony).

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