If you’ve spent any time on Hip-Hop Twitter or argued in a barbershop lately, you know Jermaine Cole is basically the patron saint of the "underrated" superstar. It’s a weird paradox. The man sells out arenas and goes platinum with no features, yet there’s this lingering cloud over his trophy shelf. People constantly ask: has j cole won a grammy, or is he just the guy who gets invited to the party but never gets to hold the mic at the end of the night?
Honestly, the answer isn't a simple yes or no if you're looking for that "Best Rap Album" solo win.
J. Cole has actually won two Grammy Awards.
But here’s the kicker—neither of them were for his own solo studio albums. For a guy who built an entire brand on being a lone wolf ("Platinum with no features," remember?), his only trips to the podium came from helping other people win. It’s a bit ironic, isn't it? He spent years pouring his soul into projects like 2014 Forest Hills Drive and 4 Your Eyez Only, only to see the Recording Academy look the other way until he hopped on a track with 21 Savage and later, Lil Durk.
The Breakthrough: 21 Savage and "A Lot"
For the longest time, the "Cole has no Grammys" meme was a real thing. It peaked around 2019. Then 2020 rolled around, and the drought finally ended. J. Cole won his first-ever Grammy for Best Rap Song thanks to his guest verse on 21 Savage’s "A Lot."
If you listen to that verse, it makes sense. He wasn't just rapping; he was mentoring. He gave 21 Savage (and the listeners) a masterclass on longevity and the pitfalls of the industry. It was one of those "verse of the year" moments that the Academy simply couldn't ignore. Cole himself even joked about it later during his 2022 Dreamville Festival, telling the crowd that the only reason he had a trophy was because of 21 Savage.
He didn't sound bitter. He just sounded like a guy who had finally stopped looking for validation in a gold-plated gramophone.
The Second Win: "All My Life" with Lil Durk
Fast forward to the 66th Annual Grammy Awards in 2024. Cole snagged his second win, this time for Best Melodic Rap Performance for "All My Life" with Lil Durk.
This win felt different.
While "A Lot" was a gritty lyrical exercise, "All My Life" was a massive, uplifting radio hit. It featured a children’s choir and a message about overcoming the "trenches." It was exactly the kind of high-production, high-sentiment song that the Grammys love. When the news broke, Lil Durk mentioned he texted Cole immediately. Cole was on tour at the time, probably halfway across the country, just taking the win in stride.
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The Long List of "What Ifs" (Nominations vs. Wins)
To really understand the has j cole won a grammy conversation, you have to look at the sheer volume of times he’s been passed over. As of 2026, Jermaine has racked up about 18 nominations.
Think about that. 18 times he's been told "you're one of the best this year," and 16 of those times, someone else walked away with the hardware.
- The Best New Artist Snub (2012): This was the first heartbreak. He lost to Bon Iver. At the time, hip-hop fans were livid.
- 2014 Forest Hills Drive (2016): Many consider this his magnum opus. It lost Best Rap Album to Kendrick Lamar’s To Pimp a Butterfly. Hard to argue with Kendrick, but it still hurt the "Cole World" faithful.
- The KOD Oversight (2019): This one was bizarre. KOD didn’t even get a nomination for Best Rap Album, which led to a massive outcry from fans and even other artists like Q-Tip.
- The Off-Season (2022): Nominated for four awards, including Best Rap Album. He went 0-for-4 that night.
- Might Delete Later (2025): His latest project was nominated for Best Rap Album at the 2025 ceremony but lost to Doechii’s Alligator Bites Never Heal.
Why Doesn't the Academy "Get" J. Cole?
There’s a theory that Cole’s music is too "for the people" and not enough "for the industry."
He doesn’t play the game. You won't see him doing a million press circuits specifically to lobby for a win. He doesn't make music that fits into a neat, experimental box that critics love to dissect. He makes boom-bap influenced, lyrical, soulful rap that speaks to the average person's struggle. Sometimes, the Recording Academy prefers the avant-garde over the authentic.
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Also, the competition has been insane. During Cole’s peak years, he’s had to go up against peak Kendrick Lamar, peak Drake, and peak Kanye West. In any other era, J. Cole might have five or six solo trophies.
Actionable Insights for Fans and Collectors
If you're a J. Cole completionist or just trying to keep your facts straight, here's the reality of his trophy room as we stand in 2026:
- Check the Credits: When people say he hasn't won, correct them. He has two. But specify they are for Collaborations/Features, not solo albums.
- Watch the 2024 Performance: If you want to see why he won for "All My Life," go back and watch the music video or the live performances. The chemistry between him and Durk is a rare example of a "forced" industry collab actually feeling genuine.
- Don't Value the Trophy Over the Music: Cole said it best himself in his song "Fire Squad"—the awards are often just "giving away our culture." His impact on the culture and his ability to sell out the Dreamville Festival every year is a much bigger indicator of his success than a statue.
The narrative around has j cole won a grammy is always evolving. While he might not have that "Best Rap Album" trophy in his house yet, his two wins for "A Lot" and "All My Life" prove that even the Recording Academy has to acknowledge his pen eventually.
Keep an eye on his next major solo release. Given how he's been moving lately, he might just decide to finally "play the game" enough to secure that elusive solo win, or he might just keep winning on his own terms—one guest verse at a time.