Credit: Grammys

Hip hop has had a troubled past with the Grammys. The awards ceremony has been repeatedly accused of not celebrating hip hop artists and their works. In the 66 years that the awards ceremony has run, only two rap albums have taken home Album of the Year.

But my, what rap albums they are. While the Grammys has a long way to go to improve its hip hop inclusion, here’s a look at the masterpieces the awards ceremony has given props to so far.

At the 41st Grammy awards in 1999, Lauryn Hill became the first hip hop artist ever to win Album of the Year for The Miseducation of Lauryn Hill. Whitney Houston presented the award, and when she announced Hill’s name, she shouted “yes!” and “amen” in total support.

At the time, Hill was only 23 years old but had become a notable figure in hip hop. During her acceptance speech, she said, “This is crazy because this is hip hop music”, acknowledging the genre’s struggle to be seen at the awards.

Hill went on to win four more Grammys that evening – more than any other artist that year. Not only had she made history with her Album of the Year win, she became the first woman to take home five Grammys in one night. Even more impressive, Hill won another ‘Album of the Year’ in 2000 for her work as a featured artist and producer on ‘Do You Like the Way’ on the album Supernatural from rock band, Satana.

Prior to her individual win in 1999, Hill had also earned ‘Best Rap Album’ with her band, Fugees. Her ability to gather accolades both before and after her ‘Album of the Year’ win highlighted the longevity of Hill’s talent – and her place as a legend in the hip hop industry.

Five years after Lauryn Hill took home ‘Album of the Year’, Outkast followed in suit with Speakerboxxx/The Love Below. The album was the fifth studio release from Atlanta duo, Big Boi and André 3000, who chose to create a double album to exercise the different paths they were each taking in hip hop. 

Speakerboxxx from Big Boi, is charged with fast Southern rap, heavy drum machines loops, and lyrics championing Blackness. The Love Below displays André 3000’s clever production play, bringing in different genres and instruments to more soulful, sexy tracks.

Outkast were given their Album of the Year award by Faith Hill and Carlos Santana (who had previously worked with Lauryn Hill). When the album was announced, Santana held his fists in the air and exclaimed “My boys!”.

André 3000 and Big Boi then gave speeches thanking everyone involved in the creative journey of Speakerboxxx/The Love Below. They expressed gratitude for “everyone – human and divine – who made [the album] possible”. Afterwards, the two rappers hugged intensely, savouring the moment that marked the second time hip hop was given the full stage and an award at the Grammys.

Both Lauryn Hill’s and Outkast’s wins at the Grammys have been crucial for hip hop. They serve as rare but powerful times when the genre was given mainstream visibility and praise. And while The Miseducation of Lauryn Hill and Speakerboxxx/The Love Below are only two of thousands of phenomenal hip hop albums, they encapsulate a cultural legacy.