Rappers That Have Won The Most Grammy Awards

The Grammy Awards ceremony was first held in 1959.  Thirteen (13) years later, in 1973, hip-hop as a genre originated. However, the first hip-hop category at the Grammy, Best Rap Performance, didn’t exist until 1989. When it was created, it is well known that the presentation of the Best Rap Performance award was not televised. This was widely regarded as the Grammys’ lack of regard for hip-hop at the time.

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Many of the biggest personalities in hip-hop expressed their displeasure at the Academy’s decision as a result of this. In 1989, to express their displeasure, Will Smith, then known as the Fresh Prince, and DJ Jazzy Jeff decided not to boycott the ceremony, even though they were nominated and eventually won the award. This went down as the boycout Last year, 2022, marked the 50th anniversary of hip-hop. So, we look back to see which rappers have amassed the highest number of Grammy awards wins since 1989.  

10. Drake – (5 Grammys)

2013 – Best Rap Album 2016 – Best Rap/Sung Performance 2016 – Best Rap Song for “Hotline Bling” 2018 – Best Rap Song for “God’s Plan” 2023 –  Best Melodic Rap Performance for Future’s “Wait for U.”  

10. Lil Wayne – (5 Grammys)

2009 – Best Rap Album for Tha Carter III 2009 – Best Rap Solo Performance for “A Milli” 2009 – Best Rap Song for “Lollipop” (with Static Major) 2009 – Best Rap Performance by a Duo or Group for “Swagga Like Us” (with T.I., Jay-Z & Kanye West) 2017 – Best Rap Performance for “No Problem” (with Chance the Rapper & 2 Chainz)  

10. Childish Gambino – (5 Grammys)

2018 – Best Traditional R&B Performance for “Redbone” 2019 – Record of the Year for “This Is America” 2019 – Song of the Year for “This Is America” 2019 – Best Rap/Sung Performance for “This Is America” 2019 – Best Music Video for “This Is America”  

9. OutKast – (6 Grammys)

2002 – Best Rap Performance by a Duo or Group for “Ms. Jackson” 2002 – Best Rap Album for Stankonia 2003 – Best Rap Performance by a Duo or Group for “The Whole World” (featuring Killer Mike) 2004 – Best Urban/Alternative Performance for “Hey Ya!” 2004 – Album of the Year for Speakerboxxx/The Love Below 2004 – Best Rap Album for Speakerboxxx/The Love Below  

8. Dr. Dre – (7 Grammys)

1994 – Best Rap Solo Performance for “Let Me Ride” 2001 – Best Rap Performance by a Duo or Group for “Forgot About Dre” (with Eminem) 2001 – Best Rap Album for The Marshall Mathers LP (as engineer) 2002 – Producer of the Year, Non-Classical 2010 – Best Rap Performance by a Duo or Group for “Crack a Bottle” (with Eminem & 50 Cent) 2010 – Best Rap Album for Relapse (as engineer) 2020 – Best R&B Album for Ventura (as executive producer)  

7. André 3000 – (7 Grammys)

2002 – Best Rap Performance by a Duo or Group for “Ms. Jackson” 2002 – Best Rap Album for Stankonia 2003 – Best Rap Performance by a Duo or Group for “The Whole World” (featuring Killer Mike) 2004 – Best Urban/Alternative Performance for “Hey Ya!” 2004 – Album of the Year for Speakerboxxx/The Love Below 2004 – Best Rap Album for Speakerboxxx/The Love Below 2020 – Best R&B Performance for “Come Home” (with Anderson .Paak)  

6. Lauryn Hill – (8 Grammys)

1997 – Best Rap Album for The Score 1997 – Best R&B Performance by a Duo or Group with Vocals for “Killing Me Softly” 1999 – Best New Artist 1999 – Album of the Year for The Miseducation of Lauryn Hill 1999 – Best R&B Album for The Miseducation of Lauryn Hill 1999 – Best Female R&B Vocal Performance for “Doo Wop (That Thing)” 1999 – Best R&B Song for “Doo Wop (That Thing)” 2000 – Album of the Year for Supernatural (Santana album; as producer)

5. Pharrell Williams – (13 Grammys)

2004 – Best Pop Vocal Album for Justified 2004 – Producer of the Year, Non-Classical (as The Neptunes) 2007 – Best Rap Song for “Money Maker” (with Ludacris) 2014 – Album of the Year for Random Access Memories 2014 – Record of the Year for “Get Lucky” 2014 – Best Pop Duo/Group Performance for “Get Lucky” 2014 – Producer of the Year, Non-Classical 2015 – Best Pop Solo Performance for “Happy” 2015 – Best Music Video for “Happy” 2015 – Best Urban Contemporary Album for Girl 2016 – Best Rap Song for “Alright” 2019 – Best Pop Vocal Album for Sweetener 2019 – Producer of the Year, Non-Classical  

4. Eminem – (15 Grammys)

2000 – Best Rap Solo Performance for “My Name Is” 2000 – Best Rap Album for The Slim Shady LP 2001 – Best Rap Solo Performance for “The Real Slim Shady” 2001 – Best Rap Performance by a Duo or Group for “Forgot About Dre” (with Dr. Dre) 2001 – Best Rap Album for The Marshall Mathers LP 2003 – Best Music Video for “Without Me” 2003 – Best Rap Album for The Eminem Show 2004 – Best Male Rap Solo Performance for “Lose Yourself” 2004 – Best Rap Song for “Lose Yourself” 2010 – Best Rap Performance by a Duo or Group for “Crack a Bottle” (featuring Dr. Dre and 50 Cent) 2010 – Best Rap Album for Relapse 2011 – Best Rap Album for Recovery 2011 – Best Rap Solo Performance for “Not Afraid” 2015 – Best Rap/Sung Collaboration for “The Monster” (featuring Rihanna) 2015 – Best Rap Album for The Marshall Mathers LP 2

3. Kendrick Lamar – (17 Grammys)

2015 – Best Rap Song for “i” 2015 – Best Rap Performance for “i” 2016 – Best Rap Performance for “Alright” 2016 – Best Rap Song for “Alright” 2016 – Best Rap/Sung Performance for “These Walls” (with Bilal, Anna Wise and Thundercat) 2016 – Best Music Video for “Bad Blood” (with Taylor Swift) 2016 – Best Rap Album for To Pimp a Butterfly 2018 – Best Rap Album for DAMN. 2018 – Best Rap Performance for “Humble” 2018 – Best Rap Song for “Humble” 2018 – Best Music Video for “Humble” 2018 – Best Rap/Sung Performance for “Loyalty” (with Rihanna) 2019 – Best Rap Performance for “King’s Dead” (with Jay Rock, Future and James Blake) 2022 – Best Rap Performance for “Family Ties” (with Baby Keem) 2023 – Best Rap Album for Mr. Morale & the Big Steppers 2023 – Best Rap Performance for “The Heart Part 5” 2023 – Best Rap Song for “The Heart Part 5”  

2. Kanye West – (24 Grammys)

2005 – Best Rap Song for “Jesus Walks” 2005 – Best Rap Album for The College Dropout 2005 – Best R&B Song for “You Don’t Know My Name” (as songwriter) 2006 – Best Rap Song for “Diamonds from Sierra Leone” 2006 – Best Rap Solo Performance for “Gold Digger” (featuring Jamie Foxx) 2006 – Best Rap Album for Late Registration 2008 – Best Rap Album for Graduation 2008 – Best Rap Performance by a Duo or Group for “Southside” (with Common) 2008 – Best Rap Solo Performance for “Stronger” 2008 – Best Rap Song for “Good Life” (featuring T-Pain) 2009 – Best Rap/Sung Collaboration for “American Boy” (with Estelle) 2009 – Best Rap Performance by a Duo or Group for “Swagga like Us” (with T.I., Jay-Z & Lil Wayne) 2010 – Best Rap/Sung Collaboration for “Run This Town” (with Jay-Z & Rihanna) 2010 – Best Rap Song for “Run This Town” (with Jay-Z & Rihanna) 2012 – Best Rap Album for My Beautiful Dark Twisted Fantasy 2012 – Best Rap/Sung Collaboration for “All of the Lights” (featuring Rihanna, Kid Cudi & Fergie) 2012 – Best Rap Song for “All of the Lights” (featuring Rihanna, Kid Cudi & Fergie) 2012 – Best Rap Performance for “Otis” (with Jay-Z) 2013 – Best Rap Performance for “Ni**as in Paris” (with Jay-Z) 2013 – Best Rap Song for “Ni**as in Paris” (with Jay-Z) 2013 – Best Rap/Sung Collaboration for “No Church in the Wild” (with Jay-Z, Frank Ocean & The-Dream) 2021 – Best Contemporary Christian Music Album for Jesus Is King 2022 – Best Melodic Rap Performance for “Hurricane” 2022 – Best Rap Song for “Jail”  

1. Jay-Z – (24 Grammys)

1999 – Best Rap Album for Vol. 2… Hard Knock Life 2004 – Best R&B Song for “Crazy in Love” (with Beyoncé) 2004 – Best Rap/Sung Collaboration for “Crazy in Love” (with Beyoncé) 2005 – Best Rap Solo Performance for “99 Problems” 2006 – Best Rap/Sung Collaboration for “Numb/Encore” (with Linkin Park) 2008 – Best Rap/Sung Collaboration for “Umbrella” (with Rihanna) 2009 – Best Rap Performance by a Duo or a Group for “Swagga Like Us” (with T.I., Kanye West and Lil Wayne) 2010 – Best Rap Solo Performance for “D.O.A. (Death of Auto-Tune)” 2010 – Best Rap Song for “Run This Town” (featuring Rihanna and Kanye West) 2010 – Best Rap/Sung Collaboration for “Run This Town” (featuring Rihanna and Kanye West) 2011 – Best Rap/Sung Collaboration for “Empire State of Mind” (featuring Alicia Keys) 2011 – Best Rap Song for “Empire State of Mind” (featuring Alicia Keys) 2011 – Best Rap Performance by a Duo or a Group for “On to the Next One” (featuring Swizz Beatz) 2012 – Best Rap Performance for “Otis” (with Kanye West) 2013 – Best Rap Performance for “Ni**as in Paris” (with Kanye West) 2013 – Best Rap Song “Ni**as in Paris” (with Kanye West) 2013 – Best Rap/Sung Collaboration for “No Church in the Wild” (with Kanye West, Frank Ocean & The-Dream) 2014 – Best Rap/Sung Collaboration for “Holy Grail” (featuring Justin Timberlake) 2014 – Best Music Video for “Suit & Tie” (with Justin Timberlake) 2015 – Best R&B Performance for “Drunk in Love” (with Beyoncé) 2015 – Best R&B Song for “Drunk in Love” (with Beyoncé) 2019 – Best Urban Contemporary Album for Everything Is Love (with Beyoncé as The Carters) 2021 – Best Rap Song for “Savage” (as songwriter) 2022 – Best Rap Song for “Jail” (with Kanye West)  

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