15 Rappers with the Most Grammy Award Wins » Amazfeed

15 Rappers with the Most Grammy Award Wins

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.

YearsAwardSong
2002Best Rap Performance by a DuoMs. Jackson
2002Best Rap AlbumStankonia
2003Best Rap Performance by a Duo or GroupThe Whole World” (featuring Killer Mike)
2004Album of the YearSpeakerboxxx/The Love Below
2004Best Rap AlbumSpeakerboxxx/The Love Below
2004Best Urban/Alternative PerformanceHey Ya!

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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.

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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.

YearsAwardSong
2009Best Rap AlbumTha Carter III
2009Best Rap Solo PerformanceA Milli
2009Best Rap Song“Lollipop” (with Static Major)
2009Best Rap Performance by a Duo or Group“Swagga Like Us” (with T.I., Jay-Z & Kanye West)
2017Best Rap Performance“Truffle Butter” (with Nicki Minaj & Drake)

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.

YearsAwardSong
2019Song of the YearThis is America
2019Best Music VideoThis Is America
2019Best Rap/Sung PerformanceThis is America
2018Best Traditional R&B PerformanceRedbone

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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.

YearsAwardSong
2004Best Pop Vocal AlbumJustified
2004Producer of the YearNon-Classical (as The Neptunes)
2007Best Rap Song“Money Maker” (with Ludacris)
2014Album of the YearRandom Access Memories
2014Record of the Year“Get Lucky”
2014Best Pop Duo/Group Performance“Get Lucky”
2014Producer of the YearNon-Classical
2015Best Pop Solo Performance“Happy”
2015Best Music Video“Happy”
2015Best Urban Contemporary AlbumGirl
2016Best Rap Song“Alright”
2019Best Pop Vocal AlbumSweetener
2019Producer of the YearNon-Classical

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.

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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.

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

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.

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YearsAwardSong
1994Best Rap Solo PerformanceLet Me Ride
2001Best Rap Performance by a Duo or Group“Forgot About Dre” (with Eminem)
2001Best Rap AlbumThe Marshall Mathers LP (as engineer)
2002Producer of the YearNon-Classical
2010Best Rap Performance by a Duo or Group“Crack a Bottle” (with Eminem & 50 Cent)
2010Best Rap AlbumRelapse (as engineer)
2020Best R&B AlbumVentura (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.

YearsAwardSong
2002Best Rap Performance by a Duo or Group“Ms. Jackson”
2002Best Rap AlbumStankonia
2003Best Rap Performance by a Duo or Group“The Whole World” (featuring Killer Mike)
2004Best Urban/Alternative Performance“Hey Ya!”
2004Album of the YearSpeakerboxxx/The Love Below
2004Best Rap AlbumSpeakerboxxx/The Love Below
2020Best 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.

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

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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.

YearsAwardSong
2000Best Rap Solo PerformanceMy Name Is
2000Best Rap AlbumThe Slim Shady LP
2001Best Rap Solo PerformanceThe Real Slim Shady
2001Best Rap Performance by a Duo or GroupForgot About Dre” (with Dr. Dre)
2001Best Rap AlbumThe Marshall Mathers LP
2003Best Music VideoWithout Me
2003Best Rap AlbumThe Eminem Show
2004Best Male Rap Solo PerformanceLose Yourself
2004Best Rap SongLose Yourself
2010Best Rap Performance by a Duo or Group“Crack a Bottle” (featuring Dr. Dre and 50 Cent)
2010Best Rap AlbumRelapse
2011Best Rap AlbumRecovery
2011Best Rap Solo PerformanceNot Afraid
2015Best Rap/Sung CollaborationThe Monster” (featuring Rihanna)
2015Best Rap AlbumThe 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.”

YearsAwardSong
2014Best New ArtistThe Heist
2014Best Rap AlbumThe Heist
2014Best Rap Performance“Thrift Shop”
2014Best 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.

YearsAwardSong
2022Best Melodic Rap PerformanceHurricane
2022Best Rap SongJail
2021Best Contemporary Christian Music AlbumJesus Is King
2013Best Rap/Sung CollaborationNo Church in the Wild
2013Best Rap PerformanceNi**as in Paris
2013Best Rap SongNi**as in Paris.” (Jay-Z & Kanye West)
2012Best Rap SongAll of the Lights (Kanye West, Rihanna, Kid Cudi & Fergie )
2012Best Rap PerformanceOtis
2010Best Rap/Sung CollaborationRun This Town
2010Best Rap SongRun This Town (Jay-Z, Rihanna & Kanye West)
2009Best Rap/Sung CollaborationAmerican Boy
2009Best Rap Performance by a Duo or GroupSwagga Like Us
2008Best Rap AlbumGraduation
2008Best Rap Solo PerformanceStronger
2008Best Rap Performance by a Duo or GroupSouthside
2008Best Rap SongGood Life
2006Best Rap AlbumLate Registration
2006Best Rap Solo PerformanceGold Digger
2006Best Rap SongDiamonds From Sierra Leone
2005Best Rap SongJesus Walks
2005Best Rap AlbumThe College Dropout
2005Best R&B SongYou 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.

YearsAwardSong
2023Best Melodic Rap PerformanceWait for U
2019Best Rap SongGod’s Plan
2017Best Rap/Sung PerformanceHotline Bling
2017Best Rap SongHotline Bling
2013Best Rap AlbumTake 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.

YearsAwardSong
2017Best New ArtistHimself
2017Best Rap PerformanceNo Problem
2017Best Rap AlbumColoring Book
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