The 23 Most Surprising Grammy Winners of All Time

1 | Alvin and the Chipmunks

At the inaugural Grammy Awards in 1959, Alvin, Simon, and Theodore of David Seville and the Chipmunks were nominated for not one, not two, but three Grammys. The adorable anthropomorphic rodents had captured America with their holiday ditty "The Chipmunk Song (Christmas Don't Be Late)" and they took home Grammys gold in two categories: Best Comedy Performance and Best Recording for Children. (It was also nominated for Record of the Year, but lost to "Nel Blu Dipinto Di Blu (Volare)" by Domenico Modugno.) Of course, Alvin was only in it for the hula hoop anyway.

2 | Carrie Fisher

About a year after her death in Dec. 2016, Carrie Fisher was honored by the Recording Academy in Jan. 2018 with the Grammy for Best Spoken Word Album for the audiobook of her memoir The Princess Diarist. (She had been nominated previously in 2009 for the audiobook of Wishful Drinking.) Billie Lourd, Fisher's only daughter, posted on Instagram about her mom's win: "Princess Diarist was the last profesh(ish) thing my momby and I got to do together ... We’ll celebrate in true Carrie style: in bed in front of the TV over cold Coca-Colas and warm e-cigs."

3 | Magic Johnson

NBA star Magic Johnson, who announced his HIV-positive status in 1991, was awarded the 1993 Grammy for Best Spoken Word Album for What You Can Do to Avoid AIDS, the audio version of his groundbreaking book.

"I decided to do it because education, especially for young people, is our best weapon in the battle against AIDS. I think young people are going to listen to what I have to say," Johnson told The Baltimore Sun at the time. "I'm going to keep spreading the word until we stop this epidemic."

4 | Kate Winslet

Actress Kate Winslettook home the Grammy for Best Spoken Word Album for Children in 2000 for her narration of Listen to the Storyteller: A Trio of Musical Tales from Around the World. Because she also has an Oscar (for The Reader) and an Emmy (for Mildred Pierce), the actress only needs a Tony to join the exclusive club of people who have an EGOT—an Emmy, a Grammy, an Oscar, and a Tony.

5 | Audrey Hepburn

Speaking of the EGOT, Audrey Hepburn posthumously earned her membership when she won a Grammy in 1994. Two years after her death, she won Best Spoken Word Album for Children for her narration of Audrey Hepburn's Enchanted Tales. Hepburn dedicated most of her later years to helping children, working on behalf of UNICEF in some of the poorest communities in Africa, South America, and Asia.

6 | Martin Luther King Jr.

Martin Luther King Jr.'s famous opposition to the Vietnam War earned him a Grammy in 1971. The Civil Rights leader won the Grammy for Best Spoken Word Recording posthumously for the speech he gave about the war at Riverside Church in New York in 1967.

His most famous speech, "I Have a Dream," was also nominated for a Grammy in 1969. But his first Grammy nomination was for Best Documentary, Spoken Word or Drama Recording, for "We Shall Overcome," in 1964.

7 | Steve Jobs

Just months after his death, Apple co-founder Steve Jobs won the 2012 Grammy Trustees Award, an honor bestowed upon those who have influenced the music industry in areas unrelated to performance. With all of the ways Apple has enhanced our listening and sharing experience over the years, first with the iPod and iTunes and then with Apple Music, the Recording Academy honored Jobs for how he "revolutionized the industry."

8 | Barack Obama

Believe it or not, the 44th president of the United States has won two Grammys, both in the Best Spoken Word Album category. His first was for Dreams From My Father in 2006, and his second was for The Audacity of Hope: Thoughts on Reclaiming the American Dream in 2008.

9 | Hillary Clinton

Obama is hardly the only politician who has snagged a Grammy. Hillary Clinton was awarded Best Spoken Word Album for her audiobook It Takes a Village in 1997. She was nominated again in the same category for Living History in 2004, but lost to another surprising Grammy winner, who you'll read about later. It turns out that the Clintons and the Grammys go hand in hand.

10 | Bill Clinton

No, the former U.S. president wasn't awarded a Grammy for his saxophone skills, but he does have two of the coveted awards. Bill Clintonpicked up his first Grammy in the Best Spoken Word Album for Children category in 2004 for his narration on Peter and the Wolf / Wolf Tracks. The following year, he won the Grammy for Best Spoken Word Album for his audiobook of My Life.

11 | Sophia Loren

Clinton shared his first Grammy with some more unlikely company, including silver screen icon Sophia Loren. Their recording combined the works Peter and the Wolf and Wolf Tracks, with Clinton reading the latter's narration and Loren reading the former's. So, she too won the Grammy for Best Spoken Word Album for Children in 2004.

12 | Mikhail Gorbachev

But wait, the weirdness continues! Mikhail Gorbachev, the former president of the Soviet Union, also served as a narrator on Peter and the Wolf / Wolf Tracks. He read the story's three spoken-word sections—the introduction, intermezzo, and epilogue—in Russian, so he's also among the work's Grammy winners.

13 | Patrick Stewart

As you may have realized, the Grammys really love Peter and the Wolf. And Patrick Stewart also won the Grammy for Best Spoken Word Album for Children in 1996 for his narration of the children's story. In addition to Stewart, Clinton, Loren, and Gorbachev, dozens of other celebrities have taken on this narrating task, like David Bowie, Sharon Stone, Sting, Melissa Joan Hart, Ben Kinglsey, Carol Channing, and Alice Cooper.

14 | Zach Braff

In 2005, actor and music lover Zach Braffwon the Grammy for Best Compilation Soundtrack for Visual Media for the soundtrack to Garden State, a film he wrote, starred in, and directed. "Essentially, I made a mix CD with all of the music that I felt was scoring my life at the time I was writing the screenplay," he told IGN Music. And it certainly paid off.

15 | Betty White

In 2012, at 90 years young, actress Betty White took home a Grammy for her audiobook If You Ask Me (and of Course You Won't) for Best Spoken Word Album. Shortly before that win, White also won the Screen Actors Guild Award for Outstanding Female Actor in a Comedy series for Hot in Cleveland. Fun fact: For both awards, White beat out Tina Fey!

16 | Stephen Colbert

Like former presidents Obama and Clinton, Stephen Colbert has won two Grammys: one for Best Comedy Album for A Colbert Christmas: The Greatest Gift of All! in 2010, and the other for Best Spoken Word Album for his audiobook America Again: Re-becoming the Greatness We Never Weren't in 2014.

17 | Michael J. Fox

Michael J. Fox may have had to leave acting behind due to his Parkinson's disease, but he's certainly been staying active by penning compelling stories about his life that've earned major accolades. In 2010, for example, Fox took home the Grammy for Best Spoken Word Album for the audio version of his book Always Looking Up: The Adventures of an Incurable Optimist.

"People say, 'How do you achieve this?' And you hear, 'Just keep your head down.' But I find the opposite is true: Keep your head up," he told Good Housekeeping.

18 | David Fincher

Director David Fincher is famous for helming The Curious Case of Benjamin Button, Fight Club, and The Social Network. But before he was an Oscar winner, he was behind many iconic music videos.

In fact, since 1984, Fincher has directed more than 50 music videos for artists like Madonna, Rick Springfield, and Michael Jackson. Two of the videos he's directed have earned him Grammys for Best Music Video: "Love is Strong" by The Rolling Stones in 1995 and "Suit & Tie" by Justin Timberlake and Jay-Z in 2014.

19 | Tia Carrere

The woman often thought of as Wayne's World's Cassandra Wong is far more than the sexy rocker Mike Myers falls for. Tia Carrere is also an accomplished Hawaiian musician. She took home the Grammy for Best Hawaiian Music Album in both 2009 and 2011. Plus, she has two other nominations under her belt.

20 | Al Franken

Comedian-turned-senator Al Frankenwon Grammys for Best Comedy Album in 1997 for Rush Limbaugh Is a Big Fat Idiot, and Best Spoken Word Album in 2004 for Lies and the Lying Liars Who Tell Them: A Fair and Balanced Look at the Right, beating out Hillary Clinton for the latter. And that's not all: He was nominated for five other Grammys on top of that!

21 | Whoopi Goldberg

Actress Whoopi Goldbergwon her Grammy back in 1986 for Best Comedy Recording for Whoopi Goldberg: Direct from Broadway. It was the first of the four awards that got her an EGOT. The second was her 1992 Oscar for Best Supporting Actress in Ghost, and then she earned her remaining two awards in 2002. That year, Goldberg won her first Daytime Emmy Award for Outstanding Special Class Special for Beyond Tara: The Extraordinary Life of Hattie McDaniel, and her Tony Award for Best Musical for Thoroughly Modern Millie.

22 | Martin Scorsese

Filmmaker Martin Scorsese has had an incredibly accomplished career, so it's probably not a total shock that he's managed to snag a Grammy during his five decades in Hollywood. After two nominations in 2004 and 2005, Scorsese finally won the 2006 Grammy for Best Long Form Music Video for No Direction Home, a documentary that traced the life and career of Bob Dylan.

23 | Joaquin Phoenix

In 2007, Joaquin Phoenixwon a Grammy for his renditions of tons of Johnny Cash classics in the hit movie Walk the Line. The film—and thusly, the actor's vocals—won Best Compilation Soundtrack Album for Visual Media at the 2007 Grammys.