Hip-Hop’s complicated relationship with the Grammy Awards dates back to 1989 when the institution introduced the Best Rap Song category. Although the recognition may have seemed groundbreaking for mainstream music and prominent establishments accepting the genre, the nominees were notified that the award would be part of the evening’s earlier, non-televised ceremony.
Most of the nominated acts boycotted the ceremony and were met with industry-wide support. In the years following, the Grammys have been a Hip-Hop controversy hot-bed whether artists decide to speak out against the lack of mutual camaraderie between the culture and the Recording Academy, top-selling emcees absent from nomination lists and without a win on their resumes, or a mindblowing win (see Macklemore beating Kendrick Lamar in 2014).
Still, there has been progress in how the Grammys choose to recognize rap and its awarded artists. Despite past controversies and the almost shut-out in 1989, rappers have since shown up and shown out on the Grammy Awards red carpet.
Check out some of the most stylish and most memorable moments from Hip-Hop’s top representatives at the Grammy Awards throughout the years.