Every Best Rap Song Winner at the Grammy Awards Each Year

XXL celebrates 50 years of hip-hop with this feature.

Although the Grammy Awards came out in 1959, The Recording Academy didn’t debut the Best Rap Performance award until 1989, a year in which it was awarded to DJ Jazzy Jeff & The Fresh Prince for “Parents Just Don’t Understand.” Next came the Best Rap Album category in 1996, which was awarded to Naughty By Nature’s Poverty’s Paradise, decades after the genre burst onto the scene. The Grammys finally unveiled the Best Rap Song category for the 46th Grammy Awards in 2004. The first honor went to Eminem for his diamond-selling track “Lose Yourself,” marking his ninth Grammy win altogether at the time.

The Grammys and the genre of hip-hop have long-held a contentious relationship with one another. One reason that tension remains is credited to Macklemore’s 2014 wins for Best Rap Song with “Thrift Shop,” as well as Best Rap Album with The Heist. In the process, many fans thought that Macklemore’s competitors at the time, Kendrick Lamar, Drake and Jay-Z, were snubbed. Mainly, K-Dot, when Macklemore won Best Rap Album win for The Heist over good kid, m.A.A.d city.

Despite moments like that, there have been positive experiences like “Jesus Walks” by Ye (formerly known as Kanye West) winning in 2005, “Lollipop” by Lil Wayne winning in 2009, and “Humble.” by Kendrick Lamar winning in 2018. The nominees and winners in this award category have mostly been validated through the court of public opinion. More recently, the wins speak to the different states and eras of hip-hop.

The 2022 ceremony boasted many notable moments and wins from last year’s hardest-working rappers. Ye’s 2022 Best Rap Song win for “Jail” featuring Jay-Z not only rejoined a duo well-favored within hip-hop, but also spoke volumes to Ye’s long-standing reign within the genre as a producer and artist. Entering 2023, it’s important to recognize the new school as well as the veterans with artists like Jack Harlow’s “Churchill Downs” with Drake being nominated alongside Kendrick Lamar’s “The Heart Part 5.” “Pushin P” by Gunna and “Wait For U” by Future were also contenders. If you didn’t watch the awards show, take a look below to see which rapper went home with the win.

In celebration of hip-hop’s 50th anniversary this year, here, XXL takes a look at all the Grammy winners for the Best Rap Song category since it was introduced back in 2004. Check out the full list below.—Ayaa Mesbah