The Grammys and hip hop? That relationship’s been rocky since day one. Despite the fact that rap is the biggest genre in the world, the Grammys be playin’ catchup, always late to the party.
Remember when DJ Jazzy Jeff and the Fresh Prince won that first rap Grammy back in ’89? The award show didn’t even bother to televise it, showin’ how much they cared about hip hop culture. But while the Grammys snoozed, the genre only got bigger and better. Now, Jay-Z just made history, passing Quincy Jones to become the most nominated Grammy artist of all time. That’s the power of hip hop.
To celebrate these wins – all earned with struggle – check this list of the ten rappers with the most Grammy statues. We’re talkin’ legends like Andre 3000 and Lauryn Hill, plus modern kings like Kendrick Lamar. These MCs prove that no matter how much the Grammys drag their feet, true talent will always rise. Here’s the top 10 rappers droppin’ bars and snagging 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)
Jay-Z is undoubtedly one of the most decorated hip hop artists of all time, with a whopping 24 Grammy Awards to his name. He won his first award back in 1999 for Best Rap Album with
Vol. 2… Hard Knock Life
and has been a constant presence at the ceremony ever since. The iconic
Brooklyn rapper
has won awards for some of his biggest hits, including “Crazy in Love” and “Empire State of Mind,” and has also collaborated with other artists to create award-winning tracks, like “Umbrella” with Rihanna and “Numb/Encore” with Linkin Park. Hov continues to be a force to be reckoned during award season, with his most recent win in 2022 for Best Rap Song with “Jail,” a collaboration with his little brother Ye.
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”
It’s hard to overstate the impact that Kanye has had on the world of music, and
Kanye’s 24 Grammy Award Wins
are a testament to his talent and influence. He’s won in a variety of categories, from Best Rap Song for “Diamonds from Sierra Leone” and Best Rap Album for
My Beautiful Dark Twisted Fantasy
to Best Contemporary Christian Music Album for
Jesus Is King
and Best Melodic Rap Performance for “Hurricane.”
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”
With a total of 17 Grammy Awards to his name, Kendrick is already one of the most decorated hip hop artists in history. But you could make the argument that he should have at least 20 – he was nominated by didn’t win for Best New Artist, Album of the Year and Best Rap Album for
Good Kid, M.A.A.D City
. Kendrick’s first two came in 2015, when he won Best Rap Song and Best Rap Performance for “i,” then continued his winning streak at the 2016 Grammys, where he took home four awards, including Best Rap/Sung Performance for “These Walls” and Best Rap Album for
To Pimp a Butterfly
. In 2023, he took down 3 more awards when the acclaimed
Mr. Morale & the Big Steppers
and “The Heart Part 5” swept the categories.
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
Eminem’s Grammy-winning journey began in 2000 with “My Name Is” and
The Slim Shady LP
, and continued with
iconic albums
such as
The Marshall Mathers LP
,
The Eminem Show
,
Relapse
,
Recovery
, and
The Marshall Mathers LP 2
. The
Detroit rapper
has also received awards for memorable collaborations like “Forgot About Dre” with Dr. Dre, “Crack a Bottle” featuring Dre and 50 Cent, and “The Monster” featuring Rihanna.
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
No stranger to receiving awards, Pharrell Williams has been a force in the game, earning 13 Grammy Awards through his production prowess and solo ventures. From his early work with The Neptunes to his solo hit “Happy,” Skateboard P has consistently shown his versatility, working with some of the biggest names in the industry. Pharrell’s accolades not only highlight his impact on hip hop but also his lasting influence on various genres.
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)
2024 – Best Rap Performance for Killer Mike featuring André 3000, Future and Eryn Allen Kane – Scientists & Engineers
2024 – Best Rap Song for Killer Mike featuring André 3000, Future and Eryn Allen Kane – Scientists & Engineers
With genre-defying albums like
Stankonia
and
Speakerboxxx/The Love Below
, Andre and Big Boi pushed the boundaries of hip hop, earning them multiple Grammys in the process. Stack’s more recent work with Anderson .Paak on “Come Home” netted him another Grammy that he could add to his ever-growing pile.
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)
L-Boogie, the Fugees’ powerhouse vocalist and a supremely gifted solo artist, has managed to secure 8 Grammy Awards in the short time that she was active in the music game. A cultural icon, Lauryn Hill’s classic
The Miseducation of Lauryn Hill
snatched 5 Grammys in one night, including Album of the Year –
the first a hip hop album had ever won the prestigious award
. Her soulful blend of hip hop, R&B, and neo-soul has left an enduring impact on the hip hop landscape, and her Grammy wins cement her legendary status in the larger music world.
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)
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
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)