Top 30 Most Unbelievable Grammy Winners Of All Time

When you think of the Grammy Awards, names like Beyonce, Stevie Wonder, and Aretha Franklin come to mind. But in reality, many celebrities have won Grammys, even those who aren’t singers! From comedians to actors, to political figures, the Grammys have shockingly awarded the most unexpected celebs. Today we’ll count down the 30 most unexpected Grammy winners of all time – and some are just unbelievable.

#30. Esperanza Spalding

2011 was a great year for music. Many uber famous celebrities like Justin Bieber and Drake broke into the music scene that year. So when the Grammys came around, everyone thought that one of them would win, but that wasn’t the case.

Photo: Courtesy of Time Magazine

In fact, jazz singer Esperanza Spalding beat Bieber, Florence + The Machine, Mumford & Sons, and Drake, and took home the Grammy for Best New Artist. She proved everyone that fame doesn’t get you awards, but talent does, and she definitely earned it, even though most people watching had no idea who she was.

#29. Kate Winslet

British actress Kate Winslet is known for many iconic roles, such as her part in Titanic, Revolutionary Road, and Sense and Sensibility. She has won an Academy Award, a few Golden Globes, a couple of BAFTAs, an Emmy, and more, but did you know she also has a Grammy?

Photo: Courtesy of La Voz

Believe it or not, she took home the Grammy Award for Best Spoken Word Album for Children for her narration of Listen to the Storyteller. With such an impressive career we can’t help but wonder whether there is an award Winslet can’t win!

#28. Tia Carrere

Actress Tia Carrere is best known for her work as an actress on daytime soap opera General Hospital, and several movies such as Wayne’s World and Lilo & Stitch. But what many people don’t know is that Carrere is an accomplished Hawaiian singer.

Photo: Courtesy of Youtube

She has been singing since 1993, when she released her first solo album, Dream. It wasn’t until 2009, however, that she got her first Grammy Award for Best Hawaiian Music Album, and she won once again in 2011. She has also been nominated two other times.

#27. Orson Welles

Orson Welles could do no wrong. We all remember him for his fantastic work as a director, writer and producer, with films like Citizen Kane, which is considered by many people one of the best movies ever made.

Photo: Courtesy of TN

Citizen Kane was so well-received, that it earned Welles the Grammy Award for Best Spoken Word Recording in 1979 for the complete soundtrack. Welles won once again in 1981 for his role on Donovan’s Brain.

#26. Baha Men

When you think of the Baha Men, what comes to your mind? Yes, the ancient question that has yet to be answered: who let the dogs out? Although they never told us who did it, the Baha Men’s hit song was extremely successful in the year 2000.

Photo: Courtesy of Splinter

The song was so successful that not only did it peak on several charts, but it was also featured on many movies. So much so, that it won the Grammy Award for Best Dance Recording in 2001. Can you believe it?

#25. Magic Johnson

We all know Magic Johnson as a basketball legend. As an athlete, he won many championships and broke several records. But what many people don’t know is that Johnson also has won a Grammy. He retired from basketball in 1991 and became an AIDS activist afterward.

Photo: Courtesy of Diario AS

Among the many things he did to promote HIV/AIDS research and spread awareness about the condition, he wrote a book called What You Can Do to Avoid AIDS, which won many awards. The audio version of the book got him the 1993 Grammy for Best Spoken Word Album. To this day, he is still fighting against the disease every day.

#24. Audrey Hepburn

There are only a few people in the world who can claim that they have an EGOT —Emmy, Grammy, Oscar, and Tony awards— and Audrey Hepburn is one of them. She didn’t win a Grammy during her lifetime but did so posthumously in 1994.

Photo: Courtesy of Frases de la Vida

Not only was she an actress, singer, dancer, and activist, she also narrated a children’s book called Audrey Hepburn’s Enchanted Tales, which featured several classic fairy tales. In 1996, she was awarded the Grammy for Best Spoken Word Album for Children for her narration of the audiobook.

#23. Steve Jobs

Steve Jobs, the founder of Apple, made impressive technological advancements that made the world we know today. Thanks to the iPod, iPhone, and other devices, we have all enjoyed hours and hours of music over the years, and this contribution didn’t go unnoticed.

Photo: Courtesy of El Comercio Peru

Jobs was awarded the Grammy Trustees Award, granted to those who have made significant contributions to the field of recording that don’t involve performance. The Recording Academy gave the award to Jobs a couple of months after he passed away in 2012.

#22. Martin Scorsese

Martin Scorsese is an accomplished director. He has made countless successful movies such as Taxi Driver, The Departed, and The Wolf of Wall Street, and has won many awards including an Academy Award, a BAFTA, and five Golden Globes. But of course, he didn’t get a Grammy for his work as a movie director.

Photo: Courtesy of Neh

Scorsese actually directed a few famous music videos, such as Michael Jackson‘s Bad, and Robbie Robertson‘s Somewhere Down the Crazy River. He received two nominations in 2004 and 2005 for his work directing music videos, and he won the Grammy for Best Long Form Music Video in 2006 for No Direction Home, a documentary about the life of Bob Dylan.

#21. Zach Braff

We all know Zach Braff as the lead in the comedy Scrubs, but did you know that he has also worked as a director? His big break as a director came with 2004’s Garden State, which he wrote, directed, starred in, and also compiled the soundtrack for. The movie was made for just $2.5 million and raised over $35 million, and this success helped solidify Braff as much more than just an actor.

Photo: Courtesy of Youtube

The film was critically acclaimed, gained a cult following, and was also nominated for several awards, among them, the Grammy Award for Best Soundtrack Album. In 2005, Braff proudly took home the award, and it’s safe to say that all his hard work and ambition paid off.

#20. Martin Luther King Jr.

Dr. Martin Luther King Jr. was the most prominent spokesperson during the civil rights movement during the 1950s and 1960s, and -believe it or not- his work as an activist garnered him two Grammy nominations.  The first one came in 1964 for Best Documentary, Spoken Word or Drama Recording for We Shall Overcome.

Photo: Courtesy of The Six Fifty

The gospel song became the hymn of the civil rights movement. Later, he posthumously won the Grammy for Best Spoken Word Recording in 1971 for a speech he gave against the Vietnam War in 1967 at Riverside Church in New York.

#19. Stephen Colbert

Stephen Colbert is not only a television host, but also an actor, comedian, writer, producer, and political commentator. Although he is best known for The Colbert Report and The Late Show with Stephen Colbert, he has worked on plenty of projects ever since he started as an actor in 1984.

Photo: Courtesy of Time

Colbert took home the Grammy for Best Comedy Album for A Colbert Christmas: The Greatest Gift of All! in 2010, but that’s not all. The audio version of his book America Again: Re-becoming the Greatness We Never Weren’t received the award for Best Spoken Word Album in 2014.

#18. David Fincher

Acclaimed director David Fincher has made many films during his career, some of which have become a part of pop culture. Films such as Fight Club, The Social Network, and The Curious Case of Benjamin Button, have gotten him international recognition and many awards, including a Golden Globe and a BAFTA for Best Director.

Photo: Courtesy of Bolsamania

Aside from making movies, Fincher has worked as a music video director basically since the beginning of his career. He has made videos for artists like Rick Springfield, Madonna and Michael Jackson. But it was his work with The Rolling Stones in Love Is Strong that got him a Grammy for Best Music Video. In 2014, he won once again for Suit & Tie by Justin Timberlake and Jay-Z.

#17. Hillary Clinton

Not only is Hillary Clinton a politician, but she’s also a published writer. While she was the First Lady of the United States, she wrote It Takes a Village: And Other Lessons Children Teach Us, which is about her viewpoint of the situation of the children of America. This book actually got her a Grammy award.  But that’s not all!

Photo: Courtesy of El Correo de Madrid

After winning the Grammy for Best Spoken Word Album in 1997, she was nominated in the same category again in 2004 for her memoir Living History. Although her second book was well-received, he lost the award to someone very, very close to her, who we’ll look at later on our list. Don’t miss out!

#16. Al Franken

Al Franken made a career as a comedian over the 1980s and became a staff writer and performer on Saturday Night Live, where he worked until 1995. He pursued a career in politics on the side, and eventually became a full-time politician, and served as a Senator from Minnesota for nine years.

Photo: Courtesy of The Verge

But that’s not all he’s done all these years. He also wrote several books, such as Rush Limbaugh Is A Big Fat Idiot, which got him a Grammy for Best Comedy Album for its audio version in 1997. He won his second Grammy in 2004 for Best Spoken Word Album for another one of his books, Lies and the Lying Liars Who Tell Them: A Fair and Balanced Look at the Right. 

#15. “Weird Al” Yankovic

“Weird Al” Yankovic broke records and brought something new to the music scene that the industry was craving for. He became known for his humorous songs that make fun of pop culture, many of which are parodies of famous songs. He has also done polka medleys and original songs.

Photo: Courtesy of GRAMMY

But did you know that he has won many Grammys for them? In fact, he’s the person with the most Grammys on our list. He won a total of five Grammy Awards and was nominated —wait for it— sixteen times.

#14. Bill Clinton

Remember how we said that Hillary Clinton was nominated for a second Grammy in 2004, but she didn’t get it. She actually lost it to none other than her husband, Bill Clinton. It is well known that Clinton is a skilled saxophonist, but he didn’t get a Grammy for his musical talent.

Photo: Courtesy of INC

The former president of the United States got his first Grammy for Best Spoken Word Album for Children for his narration of Peter and the Wolf/ Wolf Tracks. And just one year later, the audiobook version of My Life, his memoir, got him the award for Best Spoken Word Album. Seems like the Clintons have a natural talent for getting Grammys!

#13. Whoopi Goldberg

Although Whoopi Goldberg is mostly doing talk shows nowadays, she has an extensive and varied career in Hollywood – in fact, she’s one of the few people who have an EGOT! On top of her work as an actress, comedian, and activist, she is also an author.

Photo: Courtesy of Vox

What got Whoopi her Grammy was her one-woman show, Whoopi Goldberg: Direct from Broadway, which received the award for Best Comedy Recording 1986. This was actually her first big award, followed by her Oscar for Best Supporting Actress in 1992.

#12. Sophia Loren

The talented Sophia Loren is one of the few surviving stars from the Golden Age of Hollywood. She starred in countless movies through the 1950s and 1960s, and also worked as a singer. During all these years, she has won countless awards, including an Academy Award, five Golden Globes, and of course, a Grammy – but not due to her singing abilities.

Photo: Courtesy of Youtube

She actually shared her Grammy with Bill Clinton. Both worked on the narration of Peter and the Wolf/ Wolf Tracks and won the Grammy for Best Spoken Word Album for Children in 2004. What an odd combination, right? Well, another very famous person also participated in the narration of the book, and he’s coming up on our list very soon, but try to guess who it is!

#11. Joaquin Phoenix

We all know Joaquin Phoenix for his work as an actor. He has starred in numerous films, such as epic film Gladiator, and To Die For, and he was actually nominated for an Academy award more than once. One role in particular, however, also got him a Grammy.

Photo: Courtesy of Rock and Pop

In 2005, he portrayed iconic musician Johnny Cash on Walk the Line. Of course, playing the part of a musician, he had to sing, and the results were incredible. So much so, that he won a Grammy for Best Compilation Soundtrack Album in 2007.

#10. Mikhail Gorbachev

Mikhail Gorbachev was the eighth and last leader of the Soviet Union, and he played a key part in the political scene of the early 1990s. He was actually awarded the Nobel Peace Prize for his pivotal role in the end of the Cold War and his work promoting peace in international relations. So, you must be wondering, how in the world did he end up winning a Grammy?

Photo: Courtesy of El Nuevo Dia

Well, turns out that the super random collaboration that got Bill Clinton and Sophia Loren a Grammy also involved Gorbachev, who also narrated a part of Peter and the Wolf / Wolf Tracks. Nobody knows who got the idea of putting these three people together, but although it was odd, they all got an award, so it was a good idea after all.

#9. Young MC

Young MC is a singer, actor, and rapper, who is best known for his hit song Bust a Move. The song was released in 1989 and reached number seven on the Billboard Hot 100. Still, to this day, the song is considered one of the best hip hop songs of all time.

Photo: Courtesy of Youtube

It was no surprise when Young MC took home the Grammy award for Best Rap Performance thanks to his hit song. Although he never reached the commercial success of Bust a Move again, he continued making music and has also dived into acting.

#8. Betty White

Betty White is a Hollywood legend, and her career spans over 80 years. In fact, she has had the longest television career of all time. She is best known for her work both on screen and behind the scenes in comedy tv series, such as The Mary Tyler Moore Show, Hot in Cleveland, and The Golden Girls.

Photo: Courtesy of El Vigia

She also published several books, the first of which was called If You Ask Me (and of Course You Won’t), an autobiography released in 2011. The audio version of the book got White the Grammy for Best Spoken Word Album.

#7. Shaggy

Shaggy is responsible for many catchy songs that blasted through everyone’s speakers during the 1990s and 2000s. His hit songs It Wasn’t Me, Boombastic, and many more earned him recognition as a musician on a global scale.

Photo: Courtesy of Nando Leaks

Although everyone has heard of Shaggy, not many people know he has not one, but two Grammys, and he was nominated more than ten times! Perhaps, it is because the Best Reggae Album is not such a popular category, but he won it twice for Boombastic in 1996, and 44/876 in 2019.

#6. Michael J. Fox

Michael J. Fox rose to fame in the 1980s thanks to his role as Marty McFly in the fantastic Back to the Future trilogy but sadly retired from acting in 2000 due to aggravated symptoms related to Parkinson’s disease, with which he was diagnosed in 1991 at the age of 29.

Photo: Courtesy of El Progreso

Luckily, he returned to acting a few years later, and he turned his hardship into inspiration. Not only he became a spokesperson and an activist against the disease, but he wrote about his experience. His book,  Always Looking Up: The Adventures of an Incurable Optimist, was an instant success and got him the Grammy for Best Spoken Word Album in 2010.

#5. Korn

Nu metal band Korn is known for pioneering their genre and making it mainstream. They entered the music scene in the early 1990s and have been successfully making music since then. As of 2012, the band sold more than 35 million copies around the world.

Photo: Courtesy of T13

Although they’re not the kind of band we are used to seeing in the Grammys – perhaps because it’s mostly Pop acts that are shown during the ceremonies – they have been nominated eight times, and have won twice. Freak on a Leash won for Best Music Video, Short Form, and Here to Stay earned the band the Grammy for Best Metal Performance.

#4. Patrick Stewart

Patrick Stewart‘s career spans almost six decades, so it’s safe to say this man has done it all. He’s best known for his roles in Star Trek: The Next Generation and the X-Men franchise, but he has also worked on stage and television. And, as you might have figured out from looking at this list, he won a Grammy. But how did that happen?

Photo: Courtesy of The Independent

Apparently, the Grammys are completely obsessed with Peter and the Wolf, because they keep giving awards to people for reading it. Just like Clinton, Loren, and Gorbachev, Stewart took home the award for Best Spoken Word Album for Children in 1996.

#3. Richard Pryor

Richard Pryor was a pioneer of stand-up comedy and is considered one of the most influential comedians of all time. During a career that spanned forty years, he not only did stand-up comedy but also starred in many comedies and action films.

Photo: Courtesy of Hollywood Reporter

Thanks to his incredible work in the comedy world, he won a total of five Grammy Awards for his iconic comedy albums in 1974, 1975, 1976 (yup, three years in a row!), 1981, and 1982. He was also awarded the Grammy Lifetime Achievement Award posthumously in 2006.

#2. Elmo

You are probably asking yourself what? how? and why? but don’t worry, we’ve got the answers for you. Aside from the Sesame Street television show, Elmo and the gang have branched out to other media, such as games, books, movies, and music. This last category actually got Elmo a Grammy Award.

Photo: Courtesy of Lightbox

In fact, he has not one, not two, but three Grammys. The beloved red puppet got his first Grammy in 1998 for Elmopalooza!. Then, he got his second Grammy for Best Musical Album for Children in 1999 for his album Adventures of Elmo in Grouchland, and lastly, another one in 2002 for Elmo & the Orchestra.

#1. Barack Obama

President Barack Obama has won not one, but two Grammy Awards. Although the 44th president of the United States has some nice pipes, he didn’t win them for singing. Like many other celebrities on our list, he won both Grammys for Best Spoken Word Album, one in 2006 and another one in 2008.

Photo: Courtesy of T13

His memoir, Dreams from My Father: A Story of Race and Inheritance, was released in 1995, but the audiobook version was released a few years later and got him his first Grammy. Then in 2008, he won thanks to  The Audacity of Hope: Thoughts on Reclaiming the American Dream, his second book, which was released in 2007.

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