fbpx

15 Rappers With The Most Grammy Award Wins

Last Updated On:

The Grammy Awards have short-sighted a lot of talented artists over the years, but even though hip hop music doesn’t get its proper dues at the Grammys, there have been multiple rappers who have won awards.

Here is the list of 15 rappers with the most Grammy Award wins. 

1. Jay-Z

JAY-Z - Big Pimpin' ft. UGK

First on our list is a well-known rapper and hip hop artist, Jay-Z, who has 24 Grammy Award wins. He first won a Grammy for Best Rap Album in 1999 for the album Vol. 2 Hard Knock Life. He won again in 2004 for Best R&B Song for Crazy In Love featuring Beyoncé. In 2021, he won Best Rap Song as a songwriter for Savage and again in 2022 for Jail, which featured Kayne West.

His music has been in multiple movies through the years including The Secret Life Of Pets, The Secret Life Of Pets 2, Freddy Got Fingered, Mile 22, Blue Streak, and Miami Vice

Recommended: Greatest rappers of all time

2. Kanye West 

Kanye West - Can't Tell Me Nothing

Speaking of Kayne West a second ago, he is next on our list with 24 Grammy Awards as well, including in 2005 for Best Rap Song for Jesus Walks. He won the Best Rap Album for The College Dropout the same year. In 2006, he bagged Best Rap Solo Performance for the track Gold Digger featuring Jamie Foxx and won Best Rap Song for Diamonds From Sierra Leone.

In 2022, he bagged Best Rap Song for Jail and Best Melodic Rap Performance for the track Hurricane. His song Power has been featured in the hit television show Gossip Girl

3. Kendrick Lamar 

Kendrick Lamar - Count Me Out

Next on our list is the artist Kendrick Lamar, who has 17 Grammy Awards including Best Rap Song and Best Rap Performance in 2015 for I. Those were his first two Grammys, and they kept coming from there with another in 2016 for Best Rap Performance for Alright. He won three in 2023 including Best Rap Song and Best Rap Performance for The Heart Part 5, and Best Rap Album for Mr. Morale & The Big Steppers.

His tracks have been in multiple movies and television shows including The First Purge, Uncut Gems, Grown-ish, and Love Island. 

4. Eminem 

Eminem - Without Me (Official Music Video)

Calling All Slim Shady fans, Eminem is on our list with 15 Grammy Awards total, which began in 2000. In that year, he won two Grammy Awards for Best Rap Solo Performance for the hit My Name Is and Best Rap Album for The Slim Shady LP. It didn’t stop there, and the next year, he bagged even more including Best Rap Solo Performance for the hit song The Real Slim Shady and Best Rap Album for The Marshall Mathers LP. 

His music has been in television shows and movies including Freddy Got Fingered, 21 Jump Street, Real Steel, Love Island, 8 Mile, Turbo, Human Resources, and Southpaw. He is thought to be one of the best rappers of our time, if not of all time, and will continue to win Grammy Awards and receive plenty of nominations proving all of his haters wrong. 

5. Pharrell Williams

Pharrell Williams - Happy (Video)

Attention all fans of the hit song Happy, Pharrell Williams is next with 13 Grammy Awards including in 2004 where he won Best Pop Vocal Album for Justified and Producer of the Year in the Non-Classical category as The Neptunes. He was nominated several times between 2005 and 2006, although he didn’t win any Grammy Awards in any category during those years. 

He won a Grammy again in 2007 in the Best Rap Song category for Money Maker but lost the Best Rap Album category. He bagged multiple Grammy Awards in 2014 for his record Get Lucky, including Record Of The Year. He won multiple awards in 2019 including for Producer of the Year and Best Pop Vocal Album. His music has been featured in movies and television shows including Family Guy, Now You See Me 2, Despicable Me 3, Hidden Figures, and The Secret Life Of Pets

6. Lauryn Hill

Lauryn Hill - Doo-Wop (That Thing) (Official Video)

Being the frontwoman for The Fugees and also having a successful solo career, Lauryn Hill makes our list with eight Grammy Awards. She has been nominated several times but won in 1997 for Best Rap Album for the hit The Score. They also bagged Best R&B Performance by a Duo or Group for their popular song Killing Me Softly

In 1999, she won Best New Artist and Album of the Year for The Miseducation Of Lauryn Hill. You may have heard her songs in Pitch Perfect 2, How To Be Single, and Queen & Slim. She also has appeared in movies including Sister Act II: Back In The Habit, which came out in 1993. She has produced and written tracks for multiple artists too, such as Mary J. Blige, Aretha Franklin, Whitney Houston, CeCe Winans, and Santana.

Recommended Next: Greatest female rappers of all time

7. André 3000 

Outkast - Roses (Official HD Video)

André 3000 is on our list with seven Grammy Award wins, including in 2002 for Best Rap Performance by a Duo or Group for Ms. Jackson and Best Rap Album Stankonia. In 2004, he won awards for Album of the Year and Best Rap Album for Speakerboxxx/The Love Below. He bagged a Grammy in 2020 in the Best R&B Performance category for the song Come Home

8. Dr. Dre 

Dr Dre - Nuthin' But A "G" Thang [Official Music Video]

Next is Dr. Dre who has seven Grammy Award wins to his name including in 1994 for Best Rap Solo Performance for his hit song Let Me Ride. In 2001, he won Best Rap Album as engineer of The Marshall Mathers LP and for Best Rap Performance by a Duo or Group for Forgot About Dre featuring Eminem. Recently, he won Best R&B Album in 2020 as executive producer on Ventura. His music has been featured in television and movies such as Love Island, Straight Out Of Compton, Dead Tone, Rough Night, and War

Recommended: Greatest hip hop producers of all time

9. OutKast 

Outkast - Hey Ya! (Official HD Video)

OutKast is a group a lot of people love because of their fun and upbeat tone, and they have won six Grammy Awards total including in 2002 for Best Rap Performance by a Duo or Group for Ms. Jackson and Best Rap Album for Stankonia. They bagged multiple awards in 2004 including Best Rap Album and Album of the Year for Speakerboxxx/The Love Below.

Their music has been in several television shows and movies including How High, Step Up 3, Run The World, Friday Night Lights, Ballers, 8 Mile, High Fidelity, and Grey’s Anatomy. 

10. Childish Gambino 

Childish Gambino - Redbone (Official Audio)

Next on our list is Childish Gambino who has won five Grammy Awards over the years including his first one in 2018 for Best Traditional R&B Performance for the track Redbone. He bagged the other four in 2019 for This is America including in the Record of the Year and Song of the Year categories. Some movies and television shows where you’ll find his music include Dear White People, Summertime, Get Out, Star, Love Island, The Resident, and Bull

11. Lil Wayne

Lil Wayne - A Milli

Lil Wayne makes our list also with five Grammy Award wins including four in 2009 for Best Rap Album for Tha Carter III, Best Rap Solo for A Milli, and Best Rap Song for Lollipop. He won again in 2017 for Best Rap Performance for the track No Problem, which featured 2 Chainz and Chance The Rapper.

You can find his music all over television and in films including The Interview, Orange Is The New Black, Shrill, Broad City, Black-ish, and Little America. He is thought to be one of the most popular rappers of the decade and he has had a lot of success. 

12. Drake 

Drake - Laugh Now Cry Later (Official Music Video) ft. Lil Durk

Up next is Drake who has won five Grammy Awards including in 2013 winning the Best Rap Album category for Take Care. He bagged two for Hotline Bling in 2017 for Best Rap Song and Best Rap/Sung Performance. His latest Grammy was in 2023 for Best Melodic Rap Performance for the track Wait For U by Future in which he was featured.

His songs have been featured on Love Island, Fairfax, Broad City, Bates Motel, and other popular shows through the years. He continues to release popular tracks and will build on his Grammy wins if he stays true to his style. 

13. Macklemore 

MACKLEMORE & RYAN LEWIS - THRIFT SHOP FEAT. WANZ (OFFICIAL VIDEO)

Macklemore makes our list with four Grammy Award wins so far in his name with all of them being in 2014 when he won Best Rap Album for The Heist. That shocked the world since everyone thought Kendrick Lamar would win, and he couldn’t even believe it when he won. He bagged Best Rap Song and Best Rap Performance for Thrift Shop and Best New Artist that year too.

You may recognize his music in movies or television shows such as He’s All That, Kevin, Life In A Year, and Dave. He is still thriving in the music world and continues to release hit songs year after year, which likely will earn him more Grammy nominations and awards in the future. 

14. Will Smith 

Will Smith - Gettin' Jiggy Wit It

Just about everyone knows about the Will Smith situation with Chris Rock, but the man has talent and he makes our list with four Grammy Awards in his name. The first time he won a Grammy was back in 1988 when he bagged the Best Rap Performance for Parents Just Don’t Understand along with DJ Jazzy Jeff. It was that year that the category for Best Rap Performance was added to the award show, which means they became the first to win a Grammy for rap music. 

He bagged three more Grammy Awards over the years, including in 1991 again with DJ Jazzy Jeff for Best Rap Performance By A Duo or Group for Summertime. In 1997, the song Men In Black, which was made for the movie of the same name, won a Grammy for Best Solo Rap Performance. Lastly, in 1998, he bagged Best Solo Rap Performance for Gettin’ Jiggy With It.

His tracks have been featured in multiple television shows and movies including Broad City, Men In Black, Daria, Austin Powers: The Spy Who Shagged Me, Aladdin, Jersey Girl, The OC, and more. At this point, he seems to have stopped recording music and likely is done winning Grammy Awards. 

15. Chance The Rapper 

Chance The Rapper - The Heart & The Tongue (2021) | [Official Music Video]

Lastly, we have Chance The Rapper who is special since he won a Grammy without ever releasing a physical record and isn’t signed to a label. He has won three Grammy Awards including Best Rap Album for Coloring Book in 2017, which was a streaming-only record release and made Grammy history. He also bagged Best New Artist and Best Rap Performance for No Problem that same year.

He has had his music in television shows and movies throughout the years including in Waves, Love, Ballers, The Chi, Somebody I Used To Know, and Sweet/Vicious. He is still making music and enjoys releasing all of his work through streaming sites and has broken through barriers with that philosophy.

Recommended Next:

Best-selling rappers of all time

Richest rappers in the world