Sunday’s (March 14) 63rd Annual Grammy Awards was a historic event. Beyoncé set the record for the most Grammy wins ever with 28 making her the most decorated artist in Grammy history while Kanye West temporarily tied her husband JAY-Z for most victories by a rapper with 22 after his Jesus Is King album took home the honors for Best Contemporary Christian Music Album. That was until Jay won his 23rd Grammy later in the show for co-writing Megan Thee Stallion’s “Savage (Remix).”

The Grammy Awards are the highest honor in musical accolades and rappers have long been fighting for proper recognition when it comes to the Recording Academy. Hip Hop has had a complicated relationship with the Grammys, but whether they admit it or not, most artists are hoping their body of work gets nominated when submitted.

With Nas finally taking home his first Grammy Award with his 2020 King’s Disease winning Best Rap Album, the legendary New York rapper is officially on the board with a victory that Royce Da 5’9 described as “Hip Hop reparations.” On the other hand, Lil Wayne expressed his frustrations with the Recording Academy on Monday by tweeting, “Fuk the Grammys.”

Nas, Megan Thee Stallion, Beyoncé & Thundercat Among 2021 Grammy Award Winners: See The Full List

As Kanye attempts to keep pace with his big brother Hov atop the Grammy rap pantheon, check out the complete Top 10 list of winningest rappers at the Grammy Awards.

10. Childish Gambino

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Number of Grammys: 5

Highlights Include: “This Is America,” (Record of the Year, Song of the Year, Best Rap/Sung Performace and Best Music Video) “Redbone” (Best Traditional R&B Performance)

9. Lil Wayne

lil wayne mike tyson roy jones jrScott Legato/Getty Images

Number of Grammys: 5

Highlights Include: “A Milli,” (Best Rap Solo Performance) “Lollipop,” (Best Rap Song) Tha Carter III (Best Rap Album)

8. Outkast

Prince Williams/WireImage

Number of Grammys: 6

Highlights Include: Speakerboxxx/The Love Below, (Album of the Year) Stankonia, (Best Rap Album) “Ms. Jackson” (Best Rap Performance by a Duo or Group)

7. Dr. Dre 

Chelsea Lauren/Getty Images for BET

Number of Grammys: 7

Highlights Include: “Let Me Ride,” (Best Rap Solo Performance) Producer of the Year, Non-Classical, Eminem’s The Marshall Mathers LP (Best Rap Album)

6. Lauryn Hill 

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Number Of Grammys: 8

Highlights Include: The Score with The Fugees, (Best Rap Album) Herself, (Best New Artist) The Miseducation of Lauryn Hill, (Album of the Year, Best R&B Album) “Doo Wop (That Thing)” (Best Female R&B Vocal Performance)

5. Pharrell

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Number Of Grammys: 13

Highlights Include: Daft Punk’s “Get Lucky,” (Record of the Year) Kendrick Lamar “Alright,” (Best Rap Song) “Happy” (Best Music Video, Best Pop Solo Performance)

4. Kendrick Lamar 

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Number Of Grammys: 13

Highlights Include: “i,” (Best Rap Song) To Pimp a Butterfly (Best Rap Album) “Humble” (Best Music Video, Best Rap Song, Best Rap Performance)

3. Eminem 


Number Of Grammys: 15

Highlights Include: The Slim Shady LP, (Best Rap Album) “Without Me,” (Best Music Video) “Lose Yourself,” (Best Rap Song) “Not Afraid” (Best Rap Solo Performance)

Lil Baby & Killer Mike Combine Their 'Bigger Picture' & 'Walking In The Snow' Lyrics For An Impactful 2021 Grammy Performance

2. Kanye West 

Kevin Winter/Getty Images for ABA

Number Of Grammys: 22

Highlights Include: The College Dropout, (Best Rap Album) “Jesus Walks,” (Best Rap Song) “Otis” with JAY-Z (Best Rap Performance) Jesus Is King (Best Contemporary Christian Music Album)

1. JAY-Z 

Courtesy of Roc Nation

Number Of Grammys: 23

Highlights Include: Vol. 2… Hard Knock Life, (Best Rap Album) “99 Problems,” (Best Rap Solo Performance) “Swagga Like Us” f. T.I., Kanye West and Lil Wayne, (Best Rap Performance by a Duo or a Group) Everything Is Love with Beyoncé (Best Urban Contemporary Album)