People Who Have Surprisingly Won a Grammy

This list is not about bad music artists but those that you would be most surprised to find that they have a Grammy. By the way this is not a troll list all of these genuinely have won a Grammy. Feel free to add any person or group who you are surprised has gotten a Grammy. Also it doesn't have to be a competitive award any accolade counts.
The Top Ten
Barack Obama Barack Hussein Obama II (born August 4, 1961) served as the 44th President of the United States from 2009 to 2017, becoming the first African-American to hold the office. A member of the Democratic Party, he previously served as a U.S. Senator from Illinois (2005 to 2008) and as an Illinois state senator... read more

Shouldn't be surprised about President Obama winning a Grammy, really. The American people loved him (and many still do).

Twice won Best Spoken Word Album in 2006 and 2008. Quite a few of the winners will be for this award.

Magic Johnson Earvin "Magic" Johnson Jr. is a retired American professional basketball player who played point guard for the Los Angeles Lakers of the National Basketball Association for 13 seasons. He is widely regarded as one of the greatest point guards in NBA history.

Uh...is a "spoken word album of year X" just a fancy way of saying these people are well-spoken?

Martin Luther King Jr Martin Luther King Jr. (born Michael King Jr.. January 15, 1929 - April 4, 1968) was an African American minister and a pioneering civil rights leader. From 1955 until his assassination in 1968, he became the most visible spokesperson for the civil rights movement. King is best known for leading nonviolent... read more

Best Spoken Word Album in 1971 (Posthumous).

Alvin And The Chipmunks Alvin and the Chipmunks, originally David Seville and the Chipmunks or simply The Chipmunks, is an American animated music group created by Ross Bagdasarian, Sr., for a novelty record in 1958. The group consists of three singing animated anthropomorphic chipmunks: Alvin, the mischievous troublemaker,... read more

Best comedy performance and best recording for children 1959 (1st awards).

I hope this is a joke, but I know it's not.

Cardi B Belcalis Marlenis Almánzar (born October 11, 1992), known professionally as Cardi B, is an American rapper, singer, songwriter, and actress. Born and raised in New York City, she became an internet celebrity by achieving popularity on Vine and Instagram. From 2015 to 2017, she appeared as a regular... read more

Sure, she's not talented, but Grammy loves popularity, not quality, so it's not a surprise.

I think she isn't talented enough to win a Grammy. The Grammys should be about skill, not popularity.

Audrey Hepburn Audrey Hepburn, born Audrey Kathleen Ruston (4 May 1929 – 20 January 1993) was a British actress and humanitarian. Recognized as a film and fashion icon, Hepburn was active during Hollywood's Golden Age. She was ranked by the American Film Institute as the 3rd greatest female screen legend in American... read more

Best spoken word album for children 1994.

David Fincher David Andrew Leo Fincher, born August 28, 1962, is an American director and producer for film, television, and music videos. He is acclaimed for directing movies such as Se7en, Fight Club, The Social Network, and Gone Girl. Fincher also created and produced the Netflix crime drama series Mindhunter.

Directed best music video in 1995 and 2014.

Charles Moniz
Steve Jobs Steven Paul Jobs (February 24, 1955  -  October 5, 2011) was an American entrepreneur and business magnate. He co-founded Apple Inc., serving as chairman and chief executive officer. He also founded NeXT, where he was chairman and CEO... read more

Grammy Trustees award 2012. (Posthumous) Not a regular award but it still counts.

Eminem Eminem, born Marshall Bruce Mathers III, is an American rapper, actor, and music producer born on October 17, 1972, in St. Joseph, Missouri. Eminem has sold over 300 million records, making him the best-selling hip-hop artist of all time. In addition to his solo career, he is a member of D12 and (with... read more

The reason this is on here (May I add I didn't add this) is because when Eminem won his first Grammy, I was surprised. I thought DMX was going to win. That's the reason why this is on here.

The Newcomers

? Megan Thee Stallion Megan Jovon Ruth Pete was born on February 15, 1995, in Houston, Texas. She is known professionally as Megan Thee Stallion and has become a prominent American rapper, singer, and songwriter. Her breakthrough came with viral hits such as Hot Girl Summer and Savage, which have earned her multiple awards... read more
? Olivia Rodrigo Olivia Isabel Rodrigo (born February 20, 2003) is an American singer-songwriter and actress who rose to fame after playing Paige Olvera in Bizaardvark and has also played Nini Salazar-Roberts in High School Musical: The Musical: The Series. She gained much more fame after the release of her debut single... read more
The Contenders
Justin Bieber Justin Drew Bieber (born March 1, 1994) is a Canadian singer, songwriter, and record producer. He currently resides in Ontario, Canada, and is Christian. He is the son of Pattie Mallette, an author... read more

You'd think someone with as much talent as a garbage can wouldn't win a Grammy, wouldn't you? Also, who sings about how yummy their wife is?

Britney Spears Britney Jean Spears (born on December 2, 1981, in McComb, Mississippi) is an American former singer and actress. She was raised in Kentwood, Louisiana. As a child, she performed acting roles in stage productions and television shows, such as The Mickey Mouse Club, before signing with Jive Records in... read more
Mikhail Gorbachev Mikhail Sergeyevich Gorbachev (March 2, 1931 - August 30, 2022) was a Russian politician and statesman who served as the last leader of the Soviet Union from 1985 until its dissolution in 1991.

Best spoken word album for children 2004.

Hillary Clinton Hillary Diane Rodham Clinton (born October 26, 1947) is an American politician, diplomat, and former lawyer who served as the 67th United States Secretary of State from 2009 to 2013, as a United States Senator representing New York from 2001 to 2009, and as First Lady of the United States from 1993... read more
Tia Carrere Tia Carrere is an American actress, singer, and model. She is known for her roles in Lilo & Stitch, True Lies, Relic Hunter, Wayne's World, and Dancing with the Stars. Carrere has won two Grammy Awards for Best Hawaiian Music Album and continues to perform and record music in that genre.

Best Hawaiian music album 2009 and 2011.

Billie Eilish Billie Eilish Pirate Baird O'Connell, professionally known as Billie Eilish, was born on December 18, 2001. She is an American singer and songwriter widely recognized for her unique style and musical innovation. Her most well-known songs include "Bad Guy," "When the Party's Over," "Bury a Friend," "Everything... read more
Kelly Clarkson Kelly Brianne Clarkson is an American singer, songwriter, and children's book author. She rose to fame in 2002 after winning the inaugural season of American Idol, which earned her a record deal with RCA Records. Clarkson's debut single, "A Moment Like This," topped the US Billboard Hot 100 and became... read more
Chris Brown Christopher Maurice "Chris" Brown (born May 5, 1989) is an American singer, songwriter, dancer, and actor. Born in Tappahannock, Virginia, he participated in his church choir and several local talent shows from a young age. He gained international notoriety in 2009 for his physical assault of singer... read more
Michelle Branch Michelle Jacquet DeSevren Branch is an American singer, songwriter, and guitarist. During the early 2000s, she released two top-selling albums, The Spirit Room and Hotel Paper. She also collaborated with Santana on the Grammy Award-winning single The Game of Love.
Pink Alecia Beth Moore, known professionally as P!NK, is an American singer, songwriter, dancer, and actress. She rose to prominence in the early 2000s with her R&B-influenced debut album Can't Take Me Home (2000). P!NK is known for her powerful vocals, acrobatic stage presence, and numerous hit singles,... read more
Lorde Ella Marija Lani Yelich-O'Connor (born November 7, 1996), better known by her stage name Lorde, is a singer-songwriter from New Zealand. She released her debut EP The Love Club in 2012 and rose to international fame with the single "Royals" at age 16... read more
Don Cheadle
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