Kendrick Lamar didn’t just win big at the 68th Annual Grammy Awards; he made history. On a night packed with standout moments, the Compton-born rapper walked away with yet another string of trophies, officially surpassing Jay-Z to become the most-awarded rapper in Grammy history. His total now sits at an unprecedented 27 Grammy wins, a new high-water mark for hip-hop artists everywhere.
It was a milestone moment for a musician whose career has been defined by evolution, intellect, and culture-shifting work. But to appreciate what Kendrick has done, you have to understand not just his journey, but also the legacy he just surpassed.
A Night To Remember in Los Angeles
The 68th Annual Grammy Awards, hosted at Los Angeles’s Crypto.com Arena, was already shaping up as a memorable ceremony. Trevor Noah returned for his final year as host, performances were stacked, and artists from across genres gathered to celebrate music from the past year. Kendrick Lamar led the night with nine nominations, the most of any artist.
By the time the dust settled, Lamar had taken home trophies in categories including Best Rap Album for GNX, Best Rap Song for “TV Off”, Best Melodic Rap Performance for “Luther” (with SZA), and Best Rap Performance for his feature on Clipse’s “Chains & Whips”. He also secured Record of the Year for “Luther,” one of the most prestigious awards of the evening.
Those five wins on one night weren’t just impressive; they pushed his lifetime total past Jay-Z’s record of 25 wins, making Lamar the most Grammy-awarded rapper of all time.
Kendrick’s Rise
Kendrick Lamar Duckworth wasn’t handed greatness. He grew up in Compton, California, and from the beginning, his music was about something more than beats and bars. Even his early mixtapes hinted at a voice that saw beyond street fame, grappling with issues of identity, race, violence, and faith long before rap was ready to celebrate that type of introspection.
His first major-label album, Section.80, was released in 2011 and introduced him as a formidable writer. But it was his 2015 classic To Pimp a Butterfly that solidified his place in music history, a sprawling, jazz-infused masterpiece that tackled systemic racism, self-worth, and cultural legacy. The album won Best Rap Album, and its impact reverberated far beyond the Grammys.
Then came DAMN., which won five Grammys, including Best Rap Album and Best Rap Song for hits like “HUMBLE.” and “DNA.” Over the years he’s built not just a trophy case, but a reputation as an artist who expands the form, not just excels within it.
With GNX in 2024, Lamar continued that trajectory, delivering a project lauded for both its musical depth and cultural resonance. It wasn’t just another rap album; it was a statement that Kendrick still had something to say, even after decades at the top of his game.
Jay-Z, the Blueprint Grammy Champion
Before Kendrick Lamar, Jay-Z was the bar. Born Shawn Carter, Jay-Z’s journey began in the Marcy Projects of Brooklyn, New York. Long before he was a billionaire businessman, he was a rapper crafting rhymes that blended street sensibilities with sharp intellect and ambition.
Over the years, Jay-Z became one of rap’s most influential figures, not just musically but culturally, crossing into fashion, sports, and business in ways few artists ever had. He became known for albums like Reasonable Doubt, The Blueprint, and The Black Album, each a staple in hip-hop canon.
Grammy recognition followed. Jay-Z collected 25 Grammy wins over his career, a tally that stood as the gold standard for rap artists for years. His wins included Best Rap Album, Best Rap/Sung Collaboration, and nods for collaborations that bridged genre gaps, like “Numb/Encore” with Linkin Park.
Beyond the Grammys, Jay-Z’s influence is undeniable. He’s paved the way for future artists and played a big role in curating cultural conversations about wealth, legacy, and identity. But records are records, and Kendrick’s night at the 2026 Grammys marked a symbolic passing of the torch.
The Numbers Don’t Lie
According to official Grammy award milestones, Kendrick now stands at 27 wins, with Jay-Z trailing at 25 in second place. Kanye West sits just behind them with 24, making these three artists the most decorated rappers in the history of the Recording Academy.
According to official Grammy award milestones, Kendrick now stands at 27 wins, with Jay-Z trailing at 25 in second place. Kanye West sits just behind them with 24, making these three artists the most decorated rappers in the history of the Recording Academy.
Lamar entered the 2026 ceremony with 22 Grammys and 57 nominations to his name, already placing him among the most honored hip-hop artists even before this historic night. His breakout came in part from sweeping categories at previous shows, including major wins at the 2025 Grammys for his diss track “Not Like Us,” where he cleaned up in Record of the Year, Song of the Year, and Best Rap Performance categories.
This year, his nine nominations, tied for the most, translated into multiple wins across both major general categories and genre-specific ones. That alone reflects the breadth of his appeal and ability to transcend rap into the broader musical landscape.
What This Record Really Means
Becoming the most-awarded rapper in Grammy history isn’t just about stacking trophies. It’s about longevity, evolution, and recognition from peers and critics alike. For Kendrick Lamar, it means his work has been consistently seen as among the best, not just in rap, but in music overall.
Unlike some artists whose acclaim peaks early and fades, Lamar has reinvented himself while staying true to his voice. He’s an artist who can make a tightly constructed narrative album one year and then push sonic boundaries the next. That makes this record more than symbolic; it’s a testament to sustained artistic excellence.
Jay-Z’s reign as the top Grammy-winning rapper lasted for years because he set such a high bar. Kendrick’s achievement doesn’t diminish Jay-Z’s legacy; it builds on it. It reflects how hip-hop has grown and how artists today are redefining what great rap can look like.
At the microphone after winning Best Rap Album for GNX, Kendrick Lamar didn’t just celebrate another trophy; he celebrated what hip-hop means to him and to culture. He framed his wins as reflections of collective effort and the enduring power of the genre.
This milestone isn’t an endpoint. With his continued output and influence, Kendrick’s story is still unfolding, and his Grammys total might rise even further in the years to come.
For fans, hip-hop artists, and music lovers, this moment marks a real shift in the landscape, a new record, yes, but also a reminder that art evolves, legends rise, and milestones are made to be broken.
