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The Grammy Awards are widely recognized as among the most prestigious musical accolades artists can receive. An artist’s receipt of a Grammy Award acknowledges their contribution to the music industry and underscores their commitment to their craft.
Within the genre of rap, in particular, the Grammy Awards are a platform for artists to showcase their lyrical ability and affirm their significance in a genre that was once considered an anomaly in the music industry. This blog post will examine the fifteen musicians who have made history by accumulating the most Grammy Awards.
From genre pioneers to contemporary rap icons, these musicians have carved out their place in the annals of music history and established themselves as legends. We will explore their discographies, cultural impact, and Grammy Award achievements.
15. OutKast
Outkast is a well-known American hip-hop collaboration founded in Atlanta, Georgia in 1992 by André “3000” Benjamin and Antwan “Big Boi” Patton. Their exceptional talent has garnered them six Grammys, including the prestigious Album of the Year award for the critically acclaimed “Speakerboxxx/The Love Below.”
Outkast’s impact on the music industry is undeniable, as they paved the way for artists who aspire to challenge conventions and break through boundaries.
| Years | Award | Song |
| 2002 | Best Rap Performance by a Duo | Ms. Jackson |
| 2002 | Best Rap Album | Stankonia |
| 2003 | Best Rap Performance by a Duo or Group | The Whole World” (featuring Killer Mike) |
| 2004 | Album of the Year | Speakerboxxx/The Love Below |
| 2004 | Best Rap Album | Speakerboxxx/The Love Below |
| 2004 | Best Urban/Alternative Performance | Hey Ya! |
Also Read: Top 50 Greatest Famous White Rappers list Of All Time With Their Biggest Hits [2023 Rank Updated]
14. Lil Wayne
Over the past decade, Lil Wayne has maintained a significant presence in the music industry. Despite some criticism of his vocal style, his lyricism and rap abilities have garnered widespread praise. Through his unique flow and lyrical prowess, he has garnered a dedicated fan base of over 35 million monthly listeners on Spotify.
Notable honors include five Grammy Awards, eleven BET Awards, four Billboard Music Awards, two MTV Video Music Awards, and eight NAACP Image Awards. Lil Wayne became the first male artist to surpass Elvis Presley for the most appearances on the Billboard Hot 100 on September 27, 2012, with 109 recordings.
| Years | Award | Song |
| 2009 | Best Rap Album | Tha Carter III |
| 2009 | Best Rap Solo Performance | A Milli |
| 2009 | Best Rap Song | “Lollipop” (with Static Major) |
| 2009 | Best Rap Performance by a Duo or Group | “Swagga Like Us” (with T.I., Jay-Z & Kanye West) |
| 2017 | Best Rap Performance | “Truffle Butter” (with Nicki Minaj & Drake) |
Also Read: 15 Rappers with The Most Grammys won by a Female
13. Childish Gambino
Donald McKinley Glover Jr., professionally known as Childish Gambino, is a multitalented American artist with acting, comedy, music, composing, directing, and producing expertise. Glover’s third album, “Awaken, My Love!” (2016), featured the smash single “Redbone,” which reached number twelve on the Billboard Hot 100 and earned him his first Grammy Award.
In 2018, Glover released “This Is America,” which debuted at number one on the Hot 100 and was nominated for four Grammy Awards, including Song and Record of the Year. 2020 saw the publication of Glover’s latest album, 3.15.20.
| Years | Award | Song |
| 2019 | Song of the Year | This is America |
| 2019 | Best Music Video | This Is America |
| 2019 | Best Rap/Sung Performance | This is America |
| 2018 | Best Traditional R&B Performance | Redbone |
Also Read: Top 10 New White Rappers list in 2023
12. Pharrell Williams
Pharrell Lanscilo Williams, a renowned American record producer, rapper, performer, songwriter, and fashion designer, has contributed significantly to the music and entertainment industries.
His exceptional talent and creativity have garnered him numerous accolades and nominations, including 13 Grammy Award nominations, three of which were for Producer of the Year, Non-Classical.
In addition, he has received two Academy Award nominations: one in 2014 for Best Original Song for “Happy” from Despicable Me 2 and another in 2017 for Best Picture as a producer of Hidden Figures. Williams recently produced five compositions for Walt Disney Pictures’ 2019 film The Lion King, marking his third collaboration with composer Hans Zimmer.
| Years | Award | Song |
| 2004 | Best Pop Vocal Album | Justified |
| 2004 | Producer of the Year | Non-Classical (as The Neptunes) |
| 2007 | Best Rap Song | “Money Maker” (with Ludacris) |
| 2014 | Album of the Year | Random Access Memories |
| 2014 | Record of the Year | “Get Lucky” |
| 2014 | Best Pop Duo/Group Performance | “Get Lucky” |
| 2014 | Producer of the Year | Non-Classical |
| 2015 | Best Pop Solo Performance | “Happy” |
| 2015 | Best Music Video | “Happy” |
| 2015 | Best Urban Contemporary Album | Girl |
| 2016 | Best Rap Song | “Alright” |
| 2019 | Best Pop Vocal Album | Sweetener |
| 2019 | Producer of the Year | Non-Classical |
Also Read: The Top 30 Best U.K. Rappers of All Time
11. Kendrick Lamar
Kendrick Lamar Duckworth is a renowned American rapper and songwriter who is recognized for his innovative musical styles and socially conscious lyricism. It is widely acknowledged that he is one of his generation’s most influential hip-hop artists.
Late in 2009, Kendrick Lamar released his self-titled extended play and subsequently formed the hip hop supergroup Black Hippy with Jay Rock, Ab-Soul, and ScHoolboy Q, who were also on the TDE label.
Throughout his career, he has been honored with numerous honors and distinctions, including 17 Grammy honors, a Primetime Emmy Award, two American Music Awards, six Billboard Music Awards, 11 MTV Video Music Awards, a Brit Award, and an Academy Award nomination.
Also Read: 15 Best White Rappers From The 90s
| Years | Award | Song |
| 2015 | Best Rap Song | “i” |
| 2015 | Best Rap Performance | “i” |
| 2016 | Best Rap Performance | “Alright” |
| 2016 | Best Rap Song | “Alright” |
| 2016 | Best Rap/Sung Performance | “These Walls” (with Bilal, Anna Wise and Thundercat) |
| 2016 | Best Music Video for | “Bad Blood” (with Taylor Swift) |
| 2016 | Best Rap Album | To Pimp a Butterfly |
| 2018 | Best Rap Album | DAMN |
| 2018 | Best Rap Performance | “Humble” |
| 2018 | Best Rap Song | “Humble” |
| 2018 | Best Music Video | “Humble” |
| 2018 | Best Rap/Sung Performance | “Loyalty” (with Rihanna) |
| 2019 | Best Rap Performance | “King’s Dead” (with Jay Rock, Future and James Blake) |
| 2022 | Best Rap Performance | “Family Ties” (with Baby Keem) |
| 2023 | Best Rap Album | Mr. Morale & the Big Steppers |
| 2023 | Best Rap Performance | “The Heart Part 5” |
| 2023 | Best Rap Song | “The Heart Part 5” |
Also Read: The Top 15 Best Philly Rappers of All Time
10. Dr. Dre
Dr. Dre is a highly distinguished American rapper and record producer ewhose real name is Andre Romell Young. His 1992 solo début studio album, The Chronic, released by Death Row Records, propelled him to become one of the best-selling American musicians of 1993.
Dr. Dre is widely recognized for his exceptional aptitude and contributions to the music industry, having received seven Grammy Awards, including Producer of the Year, Non-Classical. On Rolling Stone’s list of the 100 Greatest Artists of All Time, he is ranked at number 56.
| Years | Award | Song |
| 1994 | Best Rap Solo Performance | Let Me Ride |
| 2001 | Best Rap Performance by a Duo or Group | “Forgot About Dre” (with Eminem) |
| 2001 | Best Rap Album | The Marshall Mathers LP (as engineer) |
| 2002 | Producer of the Year | Non-Classical |
| 2010 | Best Rap Performance by a Duo or Group | “Crack a Bottle” (with Eminem & 50 Cent) |
| 2010 | Best Rap Album | Relapse (as engineer) |
| 2020 | Best R&B Album | Ventura (as executive producer) |
9. Andre 3000
Andre Lauren Benjamin, professionally known as André 3000, is a highly accomplished American rapper, performer, songwriter, record producer, and actor. Multiple Grammy Awards are among his most notable accomplishments, widely regarded as one of the most prestigious distinctions in the music industry.
In recognition of his exceptional performance as a solo artist and as a member of Outkast, André 3000 has received six Grammy Awards throughout his career. He has received awards in Best Rap Performance and Album of the Year categories. André 3000’s triumph at the Grammy Awards is a testament to his extraordinary talent and profound impact on the music industry.
| Years | Award | Song |
| 2002 | Best Rap Performance by a Duo or Group | “Ms. Jackson” |
| 2002 | Best Rap Album | Stankonia |
| 2003 | Best Rap Performance by a Duo or Group | “The Whole World” (featuring Killer Mike) |
| 2004 | Best Urban/Alternative Performance | “Hey Ya!” |
| 2004 | Album of the Year | Speakerboxxx/The Love Below |
| 2004 | Best Rap Album | Speakerboxxx/The Love Below |
| 2020 | Best R&B Performance | “Come Home” (with Anderson .Paak) |
Also Read: Top 10 Most Successful White Rappers In The World
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8. Jay-Z
Born on December 4, 1969, Shawn Corey Carter is professionally known as Jay-Z. He is a rapper, record producer, and entrepreneur from the United States. His contributions have been essential to the creative and commercial success of artists such as Kanye West, Rihanna, and J. Cole.
According to CNBC, he is the world’s richest musician as of 2023, with a net worth of $2.5 billion. Jay-Z is one of the most successful musicians in the world, having sold more than 140 million recordings. Along with Kanye West, he holds the record for the most Grammy Awards garnered with 24. Additionally, Jay-Z holds the record for the most number-one albums on the Billboard 200 with 14.
| Years | Award | Song |
| 1999 | Best Rap Album | Vol. 2… Hard Knock Life |
| 2004 | Best R&B Song | “Crazy in Love” (with Beyoncé) |
| 2004 | Best Rap/Sung Collaboration | “Crazy in Love” (with Beyoncé) |
| 2005 | Best Rap Solo Performance | “99 Problems” |
| 2006 | Best Rap/Sung Collaboration | “Numb/Encore” (with Linkin Park) |
| 2008 | Best Rap/Sung Collaboration | “Umbrella” (with Rihanna) |
| 2009 | Best Rap Performance by a Duo or a Group | “Swagga Like Us” (with T.I., Kanye West and Lil Wayne) |
| 2010 | Best Rap Solo Performance | “D.O.A. (Death of Auto-Tune)” |
| 2010 | Best Rap Song | “Run This Town” (featuring Rihanna and Kanye West) |
| 2010 | Best Rap/Sung Collaboration | “Run This Town” (featuring Rihanna and Kanye West) |
| 2011 | Best Rap/Sung Collaboration | “Empire State of Mind” (featuring Alicia Keys) |
| 2011 | Best Rap Song | “Empire State of Mind” (featuring Alicia Keys) |
| 2011 | Best Rap Performance by a Duo or a Group | “On to the Next One” (featuring Swizz Beatz) |
| 2012 | Best Rap Performance | “Otis” (with Kanye West) |
| 2013 | Best Rap Performance | “Ni**as in Paris” (with Kanye West) |
| 2013 | Best Rap Song | “Ni**as in Paris” (with Kanye West) |
| 2013 | Best Rap/Sung Collaboration | “No Church in the Wild” (with Kanye West, Frank Ocean & The-Dream) |
| 2014 | Best Rap/Sung Collaboration | “Holy Grail” (featuring Justin Timberlake) |
| 2014 | Best Music Video | “Suit & Tie” (with Justin Timberlake) |
| 2015 | Best R&B Performance | “Drunk in Love” (with Beyoncé) |
| 2015 | Best R&B Song | “Drunk in Love” (with Beyoncé) |
| 2019 | Best Urban Contemporary Album | Everything Is Love (with Beyoncé as The Carters) |
| 2021 | Best Rap Song | “Savage” (as songwriter) |
| 2022 | Best Rap Song | “Jail” (with Kanye West) |
Also Read: Top 15 underground white Rappers 2000s
5. Eminem
Marshall Bruce Mathers III, better known as Eminem, is an incredibly accomplished American rapper, songwriter, and record producer. With over 220 million estimated record sales worldwide, he is one of the best-selling musicians of all time.
Eminem’s impressive career has garnered him numerous honors, including 15 Grammy Awards, eight American Music Awards, and 17 Billboard Music Awards, in addition to an Academy Award, a Primetime Emmy Award, and an MTV Europe Music Global Icon Award. In November 2022, he was inducted into the prestigious Rock and Roll Hall of Fame to recognize his significant contribution to the music industry.
| Years | Award | Song |
| 2000 | Best Rap Solo Performance | My Name Is |
| 2000 | Best Rap Album | The Slim Shady LP |
| 2001 | Best Rap Solo Performance | The Real Slim Shady |
| 2001 | Best Rap Performance by a Duo or Group | Forgot About Dre” (with Dr. Dre) |
| 2001 | Best Rap Album | The Marshall Mathers LP |
| 2003 | Best Music Video | Without Me |
| 2003 | Best Rap Album | The Eminem Show |
| 2004 | Best Male Rap Solo Performance | Lose Yourself |
| 2004 | Best Rap Song | Lose Yourself |
| 2010 | Best Rap Performance by a Duo or Group | “Crack a Bottle” (featuring Dr. Dre and 50 Cent) |
| 2010 | Best Rap Album | Relapse |
| 2011 | Best Rap Album | Recovery |
| 2011 | Best Rap Solo Performance | Not Afraid |
| 2015 | Best Rap/Sung Collaboration | The Monster” (featuring Rihanna) |
| 2015 | Best Rap Album | The Marshall Mathers LP 2 |
4. Macklemore
Macklemore is a renowned American rapper, performer, and songwriter. He has made significant contributions to the music industry and has received numerous honors, including multiple Grammy Awards.
The Heist, Macklemore’s debut studio album, was published on October 9, 2012, and debuted at number two on the Billboard 200. He and his collaborator Ryan Lewis won four awards at the 2014 Grammy Awards ceremony, including Best New Artist, Best Rap Album for The Heist, Best Rap Song, and Best Rap Performance for “Thrift Shop.”
| Years | Award | Song |
| 2014 | Best New Artist | The Heist |
| 2014 | Best Rap Album | The Heist |
| 2014 | Best Rap Performance | “Thrift Shop” |
| 2014 | Best Rap Song | “Thrift Shop” |
3. Kanye West
American rapper, performer, songwriter, record producer, and fashion designer Kanye West, also known as Ye. He attended the Polaris School for Individual Education during his middle-class upbringing. Kanye pulled out of college at the age of 20 to pursue a music career, despite his mother being a professor. His mother ultimately came to accept his decision, despite her initial disapproval.
As one of the most successful musicians in the world, Kanye has sold more than 160 million records and received 24 Grammy Awards with 75 nominations, tying him for the tenth-most nominations of all time and tying him with Jay-Z for the most Grammy awards won by a rapper.
| Years | Award | Song |
| 2022 | Best Melodic Rap Performance | Hurricane |
| 2022 | Best Rap Song | Jail |
| 2021 | Best Contemporary Christian Music Album | Jesus Is King |
| 2013 | Best Rap/Sung Collaboration | No Church in the Wild |
| 2013 | Best Rap Performance | Ni**as in Paris |
| 2013 | Best Rap Song | Ni**as in Paris.” (Jay-Z & Kanye West) |
| 2012 | Best Rap Song | All of the Lights (Kanye West, Rihanna, Kid Cudi & Fergie ) |
| 2012 | Best Rap Performance | Otis |
| 2010 | Best Rap/Sung Collaboration | Run This Town |
| 2010 | Best Rap Song | Run This Town (Jay-Z, Rihanna & Kanye West) |
| 2009 | Best Rap/Sung Collaboration | American Boy |
| 2009 | Best Rap Performance by a Duo or Group | Swagga Like Us |
| 2008 | Best Rap Album | Graduation |
| 2008 | Best Rap Solo Performance | Stronger |
| 2008 | Best Rap Performance by a Duo or Group | Southside |
| 2008 | Best Rap Song | Good Life |
| 2006 | Best Rap Album | Late Registration |
| 2006 | Best Rap Solo Performance | Gold Digger |
| 2006 | Best Rap Song | Diamonds From Sierra Leone |
| 2005 | Best Rap Song | Jesus Walks |
| 2005 | Best Rap Album | The College Dropout |
| 2005 | Best R&B Song | You Don’t Know My Name |
2. Drake
Aubrey Drake Graham, professionally known as Drake, is a Canadian rapper, singer, and songwriter. He gained recognition by portraying Jimmy Brooks in the popular CTV teen drama series, Degrassi: The Next Generation, from 2001-2008.
Subsequently, he pursued a career in music and released his debut mixtape Room for Improvement in 2006. Drake’s first three albums, Thank Me Later (2010), Take Care (2011), and Nothing Was the Same (2013), received critical acclaim and propelled him to the forefront of the hip hop industry.
He has been honored with numerous awards, including five Grammy Awards, six American Music Awards, 34 Billboard Music Awards, two Brit Awards, and three Juno Awards.
| Years | Award | Song |
| 2023 | Best Melodic Rap Performance | Wait for U |
| 2019 | Best Rap Song | God’s Plan |
| 2017 | Best Rap/Sung Performance | Hotline Bling |
| 2017 | Best Rap Song | Hotline Bling |
| 2013 | Best Rap Album | Take Care |
1. Chance The Rapper
Chance the Rapper is an acclaimed American rapper, singer-songwriter, and record producer. Bennett, a Chicago native, released 10 Day, his debut mixtape, in 2012. Following a 10-day suspension for marijuana possession on campus, he recorded his first full-length album, 10 Day, within eight months during the 2011 academic year.
In December 2011, Bennett released a tune titled “Windows” in conjunction with the announcement of his 10 Day project. Three Grammy Awards, including the award for Best Rap Album, are among his extraordinary accomplishments.
| Years | Award | Song |
| 2017 | Best New Artist | Himself |
| 2017 | Best Rap Performance | No Problem |
| 2017 | Best Rap Album | Coloring Book |
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