A wise man—poet Gil Scott-Heron, to be exact—once said that the revolution will not be televised. The fact that someone who laid a brick into the foundation of hip-hop culture would be so prophetic almost 20 years later should come as no surprise. On February 22, 1989, the 31st annual Grammy Awards celebrated the best and brightest in music live from the Shrine Auditorium in Los Angeles, including—for the very first time—a category for Best Rap Performance. Deserving nominees included girl groups Salt-N-Pepa and JJ Fad, nemeses LL COOL J and Kool Moe Dee, and DJ Jazzy Jeff & the Fresh Prince. Despite the Grammys’ eagerly anticipated acknowledgment of rap music, the hip-hop community largely boycotted the telecast.

The reason? Weeks after announcing its nominations, the Grammys informed all rappers involved that the award presentation for their category wouldn’t be televised. “When you have 76 Grammy categories and you only have time to put 12 on air, you’ve got 64 unhappy groups of people,” a spokesperson said at the time. Arguably more tight-knit during the throes of its golden-age era, rappers organized a boycott protesting the Recording Academy’s perceived slight.

Rush Artist Management, run by rap impresario Russell Simmons and Lyor Cohen, arranged the boycott on behalf of clients LL COOL J and DJ Jazzy Jeff & the Fresh Prince. In solidarity, hip-hop artists like Slick Rick, Kid n’ Play, Public Enemy and Salt-N-Pepa united with them at an L.A. press conference before the show, where the Fresh Prince (aka a 20-year-old Will Smith) complained, “We’re ecstatic they made a rap category and we’re ecstatic we were nominated, but we think we deserve better than that.”

Not everyone agreed. The California-based JJ Fad attended anyway, in hopes that their Dr. Dre-produced hit “Supersonic” might win the historic first rap Grammy. And elder statesman Kool Moe Dee, formerly of ’70s rap group The Treacherous Three, showed up onstage in an electric-blue leather suit to dutifully present an award for Best Male R&B Vocal alongside singer Karyn White. “A much better strategy [than boycotting] would have been for everybody to go to the Grammys and make our case in that space where the world was watching,” he reasoned.

Humungous sales in hip-hop loomed just around the corner—the pop-targeted Please Hammer Don’t Hurt ’Em by MC Hammer and Vanilla Ice’s To the Extreme both dropped in 1990. So it’s not a shock that a mainstream, non-threatening single like DJ Jazzy Jeff & the Fresh Prince’s “Parents Just Don’t Understand” won the first rap Grammy ever that Wednesday night, its playful video soon leading to the creation of NBC’s The Fresh Prince of Bel-Air sitcom.

More amazing is that Kendrick Lamar, Drake and Childish Gambino would decline to perform at the 2019 Grammys because they regarded the show’s relationship to hip-hop as problematic even decades later. (Rappers hardly ever win in the Grammys’ most prestigious categories.) And yet, A Grammy Salute to 50 Years of Hip-Hop, which aired in December 2023, celebrated the genre’s half-century anniversary, the special closing with a performance by the Oscar-winning Will Smith. The Recording Academy arguably takes more steps forward than it does back when it comes to what’s now the most popular music genre in America.