Rapper with most Grammy awards feat Kanye West, Jay-Z, Eminem & Kendrick Lamar.
Hip-hop artists have had conflicting relations with the Grammy Awards for a long time. A current example is Nicki Minaj’s displeasure with how her latest blockbuster hit song “Super Freaky Girl” may perhaps be classified. Another example is Jay-years-long Z’s boycott of the yearly award show. Regardless of how certain people of the hip-hop culture feel about the Grammys, it is still one of the most prominent events in music.
Despite being disallowed from performing, Kanye West had a fantastic night at the 2022 Grammy Awards. Ye won Best Melodic Rap Performance for the Donda track ‘Hurricane‘ (with The Weeknd and Lil Baby), beating off J. Cole (‘Pride Is the Devil’ with Lil Baby), Doja Cat (‘Need to Know,’ and Lil Nas X (‘Industry Baby‘ with Jack Harlow), who were all nominated for five awards. He also won Best Rap Song for his song ‘Jail,’ which he co-wrote with Jay-Z.
Despite being producing stellar albums Grammy finally awarded him what Nas deserved 15 years back. Nas finally received his first Grammy Award for Best Rap Album for his 2020 King’s Disease, a success that Royce Da 5’9 described as “Hip Hop restitution.” Lil Wayne, on the other hand, tweeted on Monday, “F**k the Grammys,” indicating his disdain for the Recording Academy.
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Since the 1980s, it’s been evident that the Grammy Awards are clueless when it comes to hip-hop culture and music. Even though DJ Jazzy Jeff and the Fresh Prince won the first rap Grammy in 1989, their performance was not broadcast. In terms of garnering the Grammy’s appreciation for hip hop, there’s still a long way to go.
We thought it’d be interesting to build a list of the most Grammy-winning rappers in light of the recent news that Jay-Z has now surpassed Quincy Jones as the most Grammy-nominated artist in music history.
Ye had won 22 Grammys as of this year’s Grammys, dating back to a trio of wins in 2005. With 23 victories, he was only one behind Jay-Z, who was in the first place. While the victory for ‘Jail’ increased Jay’s total number of awards to 24, Ye now has the same number as him.
Even though DJ Jazzy Jeff and the Fresh Prince won the first rap Grammy in 1989, their performance was not broadcast. In terms of garnering the Grammy’s appreciation for hip hop, there’s still a long way to go.
However, in light of the recent news that Jay-Z has officially eclipsed Quincy Jones as the most Grammy-nominated artist in music history, we thought it’d be amusing to compile a list of the most Grammy-winning rappers.
In 2023, Kendrick Lamar was nominated in 8 categories at the Grammys, and the rapper took home the honour for three nods. The rapper won the honour for his for best rap album for his latest project “Mr. Morale & the Big Steppers“. He also won the awards for Best Rap Song and Best Rap Performance for his incredible track “The Heart Part 5“. At the event, JAY-Z praised Kendrick’s new album “Mr. Morale” and called it special. He also congratulated him for winning the best rap album.
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In an interview, 50 Cent stated that JAY-Z won most of his grammies because of Beyonce. “The same concept with the Super Bowl. See, they don’t understand the relationship. They were trying to get [Eminem] to do the Super Bowl without me. It wasn’t happening,” 50 said about his appearance at the Super Bowl halftime show last year in 2022.
He continued, “It’s okay for the award shows not to give me the trophies. Even JAY-Z’s career, you can look at that and say the association to Beyonce is when he started to received the 16, 17 Grammys, since he’s been with Beyonce. And you go, prior to that… [he had] one. That came with the association.
In the overall Grammy history, Beyonce is the artist with most wins ever, with a remarkable 32 trophy wins from 88 nominations. The second on the list is Quincy Jones with 28 wins (80 noms), followed by Chick Corea with 27 wins (71 noms), Alison Krauss with 27 wins (44 noms), and Stevie Wonder with 25 wins (74 noms). Jay-Z and Kanye West are the eighth and ninth most-awarded artists in Grammy history.
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Take a peek at the top 10 Grammy-winning rappers below. To catch up to Ye and Jay, the remainders have a long way to go. Check out the entire Top 10 list of Grammy Award-winning rappers as Kanye tries to stay up with Hov atop the rap pantheon.
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)
9) 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’
8) 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’
7) 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)
6) 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)
5) 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)
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’
4) 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”
Watch: Kendrick Lamar’s Daughter’s Reaction To His Grammy Win
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 Rap Song for ‘Jail’ (with Jay-Z)
2022 – Best Melodic Rap Performance for ‘Hurricane’ (with The Weeknd and Lil Baby)
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)
