And Another One… 21 Times JAY-Z Won On Music’s Biggest Night

A thorough analysis of all 21 of JAY-Z’s GRAMMY® wins so far.


By Andy James / DJBooth

From Marcy Projects to a multi-platinum mogul, JAY-Z has embodied success at the highest level for the last two decades (and counting).

JAY-Z’s glittering career is reflected in his 21 GRAMMY® awards. Hov has taken home a trophy in every hip-hop category while picking up numerous other awards for his extensive collaborative efforts.

As the 2018 GRAMMY® Awards approach, JAY-Z leads the pack. His critically acclaimed 13th studio album, 4:44, yields 8 nominations, the most of any artist this year. Among those are his very first— and long overdue — nominations for Record of the Year, Album of the Year and Song of the Year, two awards that have produced just one single hip-hop act victory between them (OutKast’s Album of the Year-winning The Speakerboxxx/The Love Below in 2004; Lauryn Hill’s The Miseducation of Lauryn Hill was categorized as R&B).

Before the 60th Annual GRAMMY® Awards take place on January 28, here’s a thorough analysis of all 21 of JAY-Z’s GRAMMY® wins so far.


Best Rap Album — Vol. 2… Hard Knock Life

Best Rap Solo Performance — “Hard Knock Life (The Ghetto Anthem)”

Best Rap Performance by a Duo or a Group — “Money Ain’t a Thang” with Jermaine Dupri

1998’s Vol. 2… Hard Knock Life was the album that turned JAY-Z into a bona fide star. Thanks to hit singles like “Can I Get A…,” “Hard Knock Life” and “Money Ain’t a Thing”—the latter two GRAMMY®-nominated themselves—Vol. 2 brought the suburbs to the hood as Hov scored his first of many No. 1 albums. At 5x Platinum, it remains his highest-selling LP to date.

So, in February 1999, it was only fitting that Vol. 2… Hard Knock Life opened JAY-Z’s account at the GRAMMYs®, winning the award for Best Rap Album.

However, due to the glaring omission of important hip-hop releases — notably, DMX’s It’s Dark and Hell Is Hot — JAY-Z wasn’t in attendance to collect his inaugural GRAMMY® award. JAY-Z skipped on the GRAMMYs® again in 2002.


Best R&B Song — “Crazy In Love” with BEYONCÉ

Best Rap/Sung Collaboration — “Crazy In Love” with BEYONCÉ

Record of the Year — “Crazy In Love” with BEYONCÉ

Best Rap Album — The Blueprint 2: The Gift & The Curse

Best Rap Song —“Excuse Me Miss” with Pharrell

Best Rap/Sung Collaboration—“Frontin’” with Pharrell

After five years, six nominations and zero wins, JAY-Z made a winning return to the GRAMMYs® in 2004.

Entering the year with six nominations, tied for most with Album of the Year winners OutKast and BEYONCÉ, Hov took home two GRAMMYs® — Best R&B Song and Best Rap/Sung Collaboration — for his “Crazy In Love” collaboration with BEYONCÉ. The soul-sampling, booty-shaking smash topped the charts and killed the clubs both home and abroad, but to the surprise of many, lost out to Coldplay’s “Clocks” for Record of the Year.

Nevertheless, BEYONCÉ was still the night’s biggest winner as she took home five GRAMMYs® in total, in addition to performing an electrifying medley of hits (including “Crazy in Love”) alongside the legendary Prince.


Best Rap Solo Performance — “99 Problems”

Best Rap Album — The Black Album

Best Rap Song — “99 Problems”

In 2005, he scooped the award for Best Rap Solo Performance for “99 Problems,” taken from 2003’s The Black Album, which was billed as Hov’s final solo album as he planned to swap the booth for the boardroom full-time (as we all know, however, he didn’t keep his mic hung up for long).

The song itself is one of JAY-Z’s most iconic hits, a master class in chest-pounding defiance and multi-character storytelling armed by Rick Rubin’s signature made-for-boombox production. If the way “99 Problems” continues to ring off in arenas to this day doesn’t justify its win for Best Rap Performance, the song’s creation does.

“He took the track in the back of the room and played it over and over again and wrote whole complicated verses in his head. It took him about half an hour. And he’d run in the other room and just do it several times, and each time he did it, the inflection and flow would be different. It would fit the beat differently, or he’d emphasize different words. Each one was its own unique performance,” Rubin remembers. “He was just very inspired by that beat, and it was a miraculous thing to behold.”

It may not have won a GRAMMY®, but like The Blueprint before it, The Black Album is still widely considered a classic album — not least by JAY-Z himself.


Best Rap/Sung Collaboration — “Numb/Encore” with Linkin Park

With one win from one nomination, JAY-Z shot 100 percent from the field at the 2006 GRAMMYs® — and once again, it was thanks to his collaborative work.

Despite announcing that The Black Album would be his last, Hov linked up with Linkin Park in 2004 to release the Collision Course EP, a hugely popular yet polarizing snapshot of the rap-rock, mashup craze of the early to mid-’00s. The project’s biggest hit, “Numb/Encore,” took home the GRAMMY® for Best Rap/Sung Collaboration.

Though the award wasn’t televised, JAY-Z still made his mark on the GRAMMYs® stage as he performed a multi-genre — and multi-generational — medley of “Numb/Encore” and The Beatles’ “Yesterday” with Linkin Park and Sir Paul McCartney.


Best Rap/Sung Collaboration — “Umbrella” with Rihanna

Song of the Year — “Umbrella” with Rihanna

Record of the Year — “Umbrella” with Rihanna

Best Rap Album — Kingdom Come

Best Rap Solo Performance — “Show Me What You Got”

JAY-Z made his formal return to recording in 2006 with the release of Kingdom Come, which earned him two nominations for Best Rap Album and Best Rap Solo Performance (“Show Me What You Got”). However, it was his opening verse on Rihanna’s “Umbrella” that notched Hov another gold gramophone at the 2008 GRAMMYs®.

The Tricky Stewart and Kuk Harrell-produced hit, which topped the Billboard Hot 100 for seven consecutive weeks and propelled a then-rising Rihanna into superstardom, won Best Rap/Sung Collaboration. As one of, if not the, defining hits of 2007, “Umbrella” was also nominated for Song of the Year — Hov’s first nod in this category — and Record of the Year, but lost out in both categories to Amy Winehouse’s “Rehab.”

We doubt JAY-Z would have been too disappointed, though; he loved “Rehab” so much he added his own verse to the song. “The JAY-Z remix is wicked,” Winehouse told MTV in 2007. “I’m flattered that he liked [the song] enough to do something with it.”


Best Rap Performance by a Duo or a Group — “Swagga Like Us” with T.I., Kanye West & Lil Wayne

Best Rap Album — American Gangster

Best Rap Song — “Swagga Like Us” with T.I., Kanye West & Lil Wayne

Best Rap Solo Performance — “Roc Boys (And the Winner Is)…”

Best Rap Performance by a Duo or a Group — “Mr. Carter” with Lil Wayne

Hate it or love it, “Swagga Like Us” is a monster of a posse cut. Anchored by a synth-soaked sample of M.I.A.’s Record-of-the-Year contender “Paper Planes,” the song assembled the rap titans: Paper Trail-era T.I., 808s & Heartbreak-era Kanye West, Tha Carter III-era Lil Wayne and JAY-Z, fresh off the release of his cinematic return-to-form, American Gangster. The song took home the GRAMMY® for Best Rap Performance by a Duo or a Group while also being nominated for Best Rap Song.

Awards aside, the biggest moment of the night came when TIP, ‘Ye, Weezy, Hov and a heavily pregnant M.I.A. performed “Swagga Like Us,” Rat Pack style. Until then, most rappers who had graced the GRAMMYs® stage had performed on their own, or like JAY-Z three years prior, had been paired with rock acts. But for those five minutes, the GRAMMY® Awards belonged to hip-hop — and no one in the building had swagger like that.


Best Rap Song — “Run This Town” with Kanye West & Rihanna

Best Rap/Sung Collaboration — “Run This Town” with Kanye West & Rihanna

Best Rap Solo Performance — “D.O.A. (Death of Auto-Tune)”

Best Rap Song — “D.O.A. (Death of Auto-Tune)”

Best Rap Performance by a Duo or a Group — “Money Goes, Honey Stay” with Fabolous

2010 marked JAY-Z’s biggest GRAMMYs® night yet. Fresh off the release of The Blueprint 3 (which wouldn’t be eligible until the following year), Hov walked away with three GRAMMY® awards from five nominations, all as a lead artist.

The Kanye West and Rihanna-assisted “Run This Town” won Best Rap Song and Best Rap/Sung Collaboration. It was JAY-Z and Rihanna’s second award together following the success of “Umbrella”’s success in 2008, and a precursor to JAY-Z and ‘Ye’s future triumphs at the GRAMMYs®.

Meanwhile, “D.O.A. (Death of Auto-Tune)” took home the award for Best Rap Solo Performance.

With the veteran producer being responsible for both “D.O.A.” and “Run This Town” (as a co-producer alongside Kanye West), 2010 also solidified JAY-Z and No I.D.’s GRAMMY®-winning partnership, which is poised for more success at this year’s awards.


Best Rap/Sung Collaboration — “Empire State of Mind” with Alicia Keys

Best Rap Song — “Empire State of Mind” with Alicia Keys

Best Rap Performance by a Duo or a Group — “On to the Next One” with Swizz Beatz

Record of the Year — “Empire State of Mind” with Alicia Keys

Best Rap Album — The Blueprint 3

Best Rap Song — “On to the Next One” with Swizz Beatz

For the second year running, JAY-Z netted a three-peat of GRAMMYs®. In 2011, the Alicia Keys-assisted “Empire State of Mind” won Best Rap Song and Best Rap/Sung Collaboration, while “On to the Next One,” featuring Hov’s frequent collaborator and Keys’ husband, super producer Swizz Beatz, took home the award for Best Rap Performance by a Duo or a Group.

“Empire State of Mind,” a timeless New York anthem that, as fate would have it, helped soundtrack the Yankees’ triumph in the 2009 World Series, represented a series of firsts for JAY-Z: it was his first No. 1 single as a lead artist; the first 5x Platinum single in his solo catalog; and his first nomination for Record of the Year as a lead artist.


Best Rap Performance — “Otis” with Kanye West

Best Rap Album — Watch The Throne with Kanye West

Best Rap Song — “Otis” with Kanye West

2011 was a blockbuster year for JAY-Z. That summer saw Hov join forces with Kanye West to release Watch The Throne, a collaborative album of epic proportions. The project broke the record for the most iTunes sales in one week (290,000 units), produced an unforgettable world tour and remains one of the biggest events in hip-hop history.

Despite a Best Rap Album nomination for Watch The Throne and a Best Rap Song nod for “Otis,” Hov took home one award for Best Rap Performance for his and West’s aforementioned Otis Redding-sampling song.


Best Rap Song — “Niggas In Paris” with Kanye West

Best Rap Performance — “Niggas In Paris” with Kanye West

Best Rap/Sung Collaboration — “No Church In the Wild” with Kanye West, Frank Ocean & The-Dream

Best Rap Performance — “I Do” with Young Jeezy & André 3000

Best Rap/Sung Collaboration — “Talk That Talk” with Rihanna

Best Short Form Music Video — “No Church in the Wild” with Kanye West, Frank Ocean & The-Dream

Watch The Throne may have missed out on an individual prize in 2012, but the album yielded a trifecta of GRAMMYs® for JAY-Z the following year. “Niggas In Paris,” Watch The Throne’s biggest and boldest hit, won Best Rap Song and Best Rap Performance.

The song went 5x Platinum, launched the career of a young producer by the name of Hit-Boy, and became famous for being played back-to-back-to-back (as many as 12 times in a row) on JAY-Z and Kanye’s Watch The Throne world tour. What’s more, it’s also the only song with “Niggas” in the title to be nominated for a GRAMMY®. That shit cray.

Meanwhile, “No Church In the Wild,” featuring Frank Ocean and The-Dream, won Best Rap/Sung Collaboration. Thanks to director Romain Gavras’ riotous video, which mirrored social and political uprisings that were happening across the world at that time, “No Church In the Wild” also earned Hov his first nomination for Best Music Video.

If three GRAMMY® wins weren’t impressive enough, JAY-Z was competing against himself in all three categories he was nominated in. G.O.O.D. Music’s posse cut “Mercy” was a contender for Best Rap Song, Young Jeezy’s “I Do” was up for Best Rap Performance, and Rihanna’s “Talk That Talk” earned a nod for Best Rap/Sung Collaboration.

The ceremony itself had JAY-Z’s personality imprinted all over it, too. Hov performed “Suit & Tie” with Justin Timberlake, poked fun of The-Dream’s “swap meet” hat while collecting the award for Best Rap/Sung Collaboration, and sipped D’USSÉ cognac directly out of one of his GRAMMY awards, an image that captures JAY-Z’s success like few others.


Best Rap/Sung Collaboration — “Holy Grail” with Justin Timberlake

Best Music Video — “Suit & Tie” with Justin Timberlake

Best Rap Album — Magna Carta…Holy Grail

Best Rap Song — “Holy Grail” with Justin Timberlake

Best Rap Performance — “Tom Ford”

Best Rap/Sung Collaboration — “Part II (On the Run)” with BEYONCÉ

Best Pop Duo/Group Performance — “Suit & Tie” with Justin Timberlake

Best Music Video — “Picasso Baby: A Performance Art Film”

On the heels of his 12th album, Magna Carta…Holy Grail, JAY-Z entered the 2013 GRAMMYs® with eight nominations, the most of any artist that year. For the first time in his career, he also kickstarted the ceremony by performing “Drunk In Love” with his wife BEYONCÉ, a stunning set that’s par for the course for music’s biggest power couple.

2014 was a noticeably quieter night for JAY-Z in terms of awards, though. While Magna Carta… Holy Grail was nominated for Best Rap Album and yielded further nods in the Best Rap Song and Best Rap Performance categories, Hov went home with Best Rap/Sung Collaboration, for his Justin Timberlake-featuring “Holy Grail,” and for the first time, Best Music Video, for his other JT collaboration, “Suit & Tie.”

The 2014 GRAMMYs® will forever be remembered for Macklemore and Ryan Lewis’ chart-topping LP, The Heist, winning Best Rap Album over Kendrick Lamar’s universally acclaimed good kid, m.A.A.d city, an upset victory that prompted even Macklemore to apologize to K.Dot. That night did, however, spark much-needed debates and scrutiny surrounding the GRAMMYs®’ voting process, which has since been changed to recognize streaming-only projects (like Chance The Rapper’s GRAMMY®-winning mixtape, Coloring Book) and allow for online voting for the 60th GRAMMY® Awards.


Best R&B Song — “Drunk in Love” with BEYONCÉ

Best R&B Performance — “Drunk in Love” with BEYONCÉ

Best Music Film — “On the Run Tour: BEYONCÉ and Jay-Z”

Eleven years after going crazy for “Crazy In Love,” the GRAMMYs® were intoxicated with Mr. and Mrs. Carter’s “Drunk In Love” in 2015. The song, which went 3x Platinum and introduced “surfbort” into our collective vocabulary, won Best R&B Song and Best R&B Performance, bringing JAY-Z’s GRAMMY® awards tally to 21.


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