In the late 1990s and early 2000s, hip-hop was undergoing a transformation. Street credibility, lyrical ferocity, and rebellion became currency in the game. At the same time, Will Smith—the clean-cut rapper turned Hollywood A-lister—remained an icon of family-friendly hip-hop success.

Enter Eminem.

Foul-mouthed, unpredictable, and fiercely competitive, Eminem was everything Will Smith wasn’t. But it wasn’t just the contrast in image that led to Eminem’s infamous diss—it was one award show comment that lit the match.

And once the fire started, Eminem didn’t hold back.

Setting the Stage: The 1999 MTV VMAs

At the 1999 MTV Video Music Awards, Will Smith accepted the award for Best Male Video. On stage, he delivered a comment that, to many, seemed harmless:

“I don’t have to curse in my records to sell.”

The line was clearly aimed at the new wave of profanity-laced rap—whether intentionally or not. But Eminem, who had just exploded onto the scene with The Slim Shady LP, took it personally.

To him, it wasn’t a neutral statement. It was a shot across the bow.

Eminem Fires Back: “The Real Slim Shady”

Less than a year later, Eminem responded in the way only he could: through music. On his 2000 hit “The Real Slim Shady,” he fired this unforgettable line:

“Will Smith don’t gotta cuss in his raps to sell records /
Well I do, so f*** him and f*** you too.”

It was more than just a diss—it was a declaration.

Eminem was staking his claim. He didn’t care about moral posturing or mainstream acceptance. He wasn’t going to apologize for his rage, his vulgarity, or his style.

What Was Really Behind the Line?

An Attack on Artistic Judgment
Eminem perceived Will’s comment as a judgment on rappers who weren’t “safe” enough. By implying that clean content was morally superior, Will—intentionally or not—questioned Eminem’s artistic integrity.

A Power Move
Dissing Will Smith was strategic. Will was one of the biggest names in entertainment. Calling him out was a way for Eminem to make headlines, disrupt the establishment, and cement himself as hip-hop’s new outlaw.

The Old Guard vs. The Disruptor
Will Smith represented an earlier generation of rappers who had “crossed over.” Eminem was kicking down the door for artists who didn’t want to clean up for the mainstream.

How Will Smith Responded

Will Smith never fired back in music. He didn’t write a diss track or respond on stage. In interviews, he maintained his usual diplomacy. At most, he lightly brushed off the controversy by saying he respected all artists’ creative choices—even if he didn’t make the same ones.

His silence was telling: he wouldn’t engage on Eminem’s level, but he didn’t walk back his original stance either.

Legacy of the Diss

What makes this moment stand out isn’t the aggression—it’s the symbolism.

The diss represented a changing of the guard in hip-hop. It marked the rise of an era where rage, rawness, and authenticity were more valuable than polish and crossover appeal.

And for Eminem, it was one of the first of many battles that would define his career.

Final Takeaway

Eminem didn’t hate Will Smith. But he hated the idea that “clean” equaled superior.
He hated the implication that his music—flawed, profane, controversial—was somehow less valid.

So he did what he always does when he feels disrespected:
He put it on wax, lit the fuse, and let the world watch the explosion.

That one line in “The Real Slim Shady” became a cultural moment.
And even today, it stands as a reminder that in Eminem’s world, every word counts—and no one, not even a Hollywood icon, is safe from his crosshairs.