Hip-hop’s complicated relationship with the Grammy Awards dates back to 1989 when the institution introduced the Best Rap Song category. While the recognition may have seemed groundbreaking for mainstream music and premier genre-accepting establishments, nominees were told the award would be part of the evening’s non-televised ceremony.
Most of the nominated acts boycotted the ceremony and were greeted with industry-wide support. In the years since, the Grammys have been a hotbed of Hip-Hop controversy, as artists decide to denounce the lack of mutual camaraderie between the culture and the Recording Academy, top-selling entertainers absent from nomination lists and without victory on their résumé, or a stunning victory (see Macklemore beating Kendrick Lamar in 2014).
Still, there has been progress in how the Grammys choose to recognize rap and its award-winning artists. Despite past controversies and the near-exclusive in 1989, the rappers have since shown up and showed up on the Grammy Awards red carpet.
Check out some of hip-hop’s most stylish and memorable moments at the Grammy Awards over the years.