It can be said quite often: Hip-hop did it first.
When Will Smith announced last month that he would join his wife, Jada Pinkett, in skipping the Oscars after no black actors were nominated for two years in a row, he put it simply: “We’re uncomfortable to stand there and say that this is O.K.”
It was a position he’d taken before. In 1989, the first time Mr. Smith stood up against the award-show establishment, he was still known as the Fresh Prince, his medium was rap, and the ceremony was the Grammys. Unlike his situation at this year’s Oscars, he was nominated. D.J. Jazzy Jeff and the Fresh Prince went on to win the first-ever rap Grammy that year, for their crossover hit “Parents Just Don’t Understand.”
But Mr. Smith was not there to collect the trophy after deciding with some of his hip-hop peers, including two other nominees in the category, not to show up because the inaugural rap performance award would not be televised. “We chose to boycott,” Mr. Smith said at the time, calling the snub a “slap in the face.” He added, “You go to school for 12 years, they give you your diploma, and they deny you that walk down the aisle.”
Things have changed, and they haven’t. At the 58th Annual Grammy Awards on Monday, the activist rapper Kendrick Lamar will be the most nominated artist across all categories, and his work on “To Pimp a Butterfly” is in contention for the biggest awards of the night. (The album could become just the third hip-hop release to win album of the year.) LL Cool J, who was among the first batch of rap nominees for his song “Going Back to Cali,” will host the show for the fifth consecutive year.
But the Grammys’ relationship with rap has progressed in fits and starts, with the awards often going to the anodyne — most recently in 2014, when the white rapper Macklemore won in three of four current rap categories over Mr. Lamar. Last year, the televised ceremony featured no rap awards for the first time in 25 years.
In 1989, “to put it bluntly, a lot of the Grammy committee was 60-year-old white men that didn’t understand this brand-new genre,” Jazzy Jeff recalled in a recent interview. “At that time, hip-hop was just starting to break out of the mind-set that it was going to die next year.”
The invention of the category (along with awards for heavy metal and bluegrass) was, at first, a welcome acknowledgment. “The excitement was through the roof; it was validation for the culture,” Jazzy Jeff said.
Then the nominated rappers were told to arrive at the February ceremony early because their award would be part of the preshow. “We were like, ‘Wait, what — are you kidding me?’ This is the first time for the category, and it’s not even on TV?” said Juana Sperling, known as MC J. B. of the group J. J. Fad, whose song “Supersonic” was nominated. (Kool Moe Dee’s “Wild Wild West” and Salt-N-Pepa’s “Push It” rounded out the category.)
As the artists involved explained, the boycott was led by Russell Simmons and Lyor Cohen of the early rap label Def Jam and the associated Rush Artist Management, which represented LL Cool J and D.J. Jazzy Jeff and the Fresh Prince.
“They had very little respect for the category,” Mr. Simmons said of the Recording Academy. Besides, he added, rebelling “was part of our DNA anyway.”
“We didn’t care what the industry thought: That was the statement. We liked our status as alternative.”
Two weeks before the ceremony, Bill Adler, the spokesman at Def Jam and Rush Artist Management, sent a publicity release blast announcing the boycott, accusing the Recording Academy of “ghetto-izing” rap and “treating us like a stepchild.” (The Grammys’ response at the time: “When you have 76 Grammy categories and you only have time to put 12 on air, you’ve got 64 unhappy groups of people.”)
But despite the closeness of the emergent hip-hop stars — most of the nominees were friends, label mates or touring partners — not everyone was on board. J. J. Fad and Kool Moe Dee attended the awards, albeit with differing agendas.
Ms. Sperling, who now works as a school nurse when not touring with her reunited group, recalled her thinking at the time: “We are teenagers, this is superexciting, and who knows if we’ll ever get this shot again?”
“And thank God, because we never did,” she said. (Still, “If I had known then what I know now, I definitely would have agreed to the boycott,” Ms. Sperling added. “We were so young. We didn’t know about politics or making a statement.”)
More dramatic was the attendance of Kool Moe Dee, by then already an elder statesman in hip-hop. “The irony was, we were boycotting at a time that they were finally acknowledging us,” he said. “A much better strategy — and a much bigger hip-hop move — would have been for everybody to go to the Grammys and make our case in that space where the world was watching.”
So while three of the nominees, joined in solidarity by rappers like Public Enemy and Slick Rick, held a news conference to make their case, Kool Moe Dee took the stage at the Shrine Auditorium in Los Angeles as a presenter — a spot offered earlier to Mr. Smith.
Before delivering the award for best male R&B vocal, Kool Moe Dee made his statement in verse:
On the behalf of all M.C.s
My co-workers and fellow nominees
Jazzy Jeff, J. J. Fad,
Salt-N-Pepa and the boy who’s bad
We personify power and a drug-free mind
And we express ourselves through rhythm and rhyme
So I think it’s time that the whole world knows
Rap is here to stay — drummer, let’s go!
The bad blood between the factions lasted only until the after-parties. “Will Smith was like my best friend at the time,” Kool Moe Dee said. “After the show, he was trying not to speak to me, trying to poker face. But when we saw each other, we just started laughing and hugging.”
Ultimately the two-pronged attack proved effective. While the boycott made pre-social-media waves in the music press, especially rap magazines like The Source and Word Up, Kool Moe Dee was an influential ambassador among the establishment, and the rap award was televised the next year.
Today, Kool Moe Dee credits the boycott with stirring up controversy. “Something needed to be done to create enough hysteria,” he said. “Going against the grain does have an impact.”
Jazzy Jeff, who went on to win another Grammy with Mr. Smith in 1992 but again was not present, said he remained impressed with the results of the protest. “We all were very, very young and thrust into a position with the eyes of the world on us,” he said. “We represented the culture well. And to see somebody like Kendrick now, it just makes you proud.”