Jay-Z has won the Grammy Award for Best Rap Album five times, more than any other artist.

DJ Jazzy Jeff & The Fresh Prince won the first Grammy Award for Best Rap Album in 1989 for their album 'He's the DJ, I'm the Rapper'.

Kanye West has won the MTV Video Music Award for Best Hip Hop Video six times, more than any other artist.

LL Cool J won the first MTV Video Music Award for Best Hip Hop Video in 1989 for his video 'Going Back to Cali'.

Jay-Z has won the BET Award for Best Hip Hop Artist six times, more than any other artist.

LL Cool J won the first BET Award for Best Hip Hop Artist in 2001.

Jay-Z has won the Soul Train Music Award for Best Hip Hop Song of the Year four times, more than any other artist.

LL Cool J won the first Soul Train Music Award for Best Hip Hop Song of the Year in 1989 for his song 'Going Back to Cali'.

Kanye West has won the American Music Award for Favorite Rap/Hip Hop Artist five times, more than any other artist.

LL Cool J won the first American Music Award for Favorite Rap/Hip Hop Artist in 1991.

Jay-Z has won the NAACP Image Award for Outstanding Hip Hop/Rap Album five times, more than any other artist.

LL Cool J won the first NAACP Image Award for Outstanding Hip Hop/Rap Album in 1991 for his album 'Mama Said Knock You Out'.

Drake has won the Billboard Music Award for Top Rap Artist five times, more than any other artist.

LL Cool J won the first Billboard Music Award for Top Rap Artist in 1991.

Drake has won the iHeartRadio Music Award for Hip Hop Artist of the Year four times, more than any other artist.

LL Cool J won the first iHeartRadio Music Award for Hip Hop Artist of the Year in 2019.