Last updated on: February 2, 2025

The Grammys Love Kendrick Lamar… But Did They Always?

You know Kendrick Lamar as a rap genius. His words hit deep, his flow is unmatched, and his storytelling? Pure gold. With 22 Grammy Awards, he stands as one of the most decorated rappers of all time.

But here’s the thing—his Grammy journey wasn’t always smooth sailing. In fact, there were moments when fans (and even Kendrick himself) were left scratching their heads. Why? Because while the Grammys love him now, it wasn’t always that way.

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The First Time Kendrick Lamar Shocked the Grammys

Back in 2014, Kendrick Lamar was already a force to be reckoned with. His album good kid, m.A.A.d city was a masterpiece. The kind of album that gets studied in college courses today. Naturally, fans expected him to sweep the Grammys.

But then—he lost Best Rap Album to Macklemore & Ryan Lewis. Yep. The Heist took the win, leaving the hip-hop world in disbelief. Even Macklemore himself felt the weight of that moment, famously texting Kendrick, “You got robbed.”

Therefore, a fire was lit. This wasn’t just about trophies—it was about respect. And Kendrick was about to make sure the Grammys never overlooked him again.

The Grammy Domination Begins

Fast forward to 2015, and the industry had no choice but to recognize him. Kendrick took home Best Rap Performance and Best Rap Song for i. It was just the beginning.

Then came 2016. To Pimp a Butterfly exploded onto the scene, redefining hip-hop with jazz, funk, and politically charged storytelling. The Grammys had to give it its due. Kendrick won Best Rap Album, Best Rap Song (Alright), and several other categories. Finally, he was getting the recognition he deserved.

 

But—even with five wins that night, he lost Album of the Year to Taylor Swift’s 1989. Another snub? Maybe. But Kendrick wasn’t done.

Kendrick Lamar Breaks the Rules (and Wins Big)

DAMN. was different. It wasn’t just another great album. It was the first rap album to ever win the Pulitzer Prize. That’s history. And when it came to the 2018 Grammys, Kendrick walked away with Best Rap Album, Best Rap Performance, and Best Rap Song (HUMBLE.).

Therefore, his status as a Grammy heavyweight was officially locked in.

But—there was still one big category he hadn’t won yet. Record of the Year.

The Grammy Moment That Changed Everything

That moment finally came at the 2025 Grammys. Kendrick Lamar’s track Not Like Us took over hip-hop, becoming more than just a song—it was a movement. And the Grammys couldn’t ignore it. That night, Kendrick won Record of the Year, Song of the Year, Best Rap Performance, Best Rap Song, and Best Music Video.

It was his ultimate Grammy moment. The full-circle victory.

So, How Many Grammys Does Kendrick Lamar Have?

As of 2025, Kendrick Lamar has a staggering 22 Grammy wins. He stands alongside hip-hop giants like Jay-Z and Kanye West, proving that lyricism, storytelling, and raw talent still matter.

But beyond the numbers, his Grammy journey tells a bigger story. A story of perseverance, cultural impact, and a rapper who refused to be overlooked.

Therefore, the real takeaway? Kendrick Lamar isn’t just winning awards. He’s rewriting history.