The restructuring was the consequence of the Recording Academy's wish to decrease the number of categories and awards and to eliminate distinctions between solo and duo or group performances.

[5] The ceremony was not without controversy; nominees Jeff and Smith led a boycott in protest of the awards presentation not being televised, and some members of the rap community felt that more qualified artists were overlooked.

[8] For the 31st Grammy Awards (1989), Best Rap Performance nominees included DJ Jazzy Jeff & The Fresh Prince for "Parents Just Don't Understand", J. J. Fad for "Supersonic" (from the album of the same name), Kool Moe Dee for "Wild Wild West", LL Cool J for "Going Back to Cali", and Salt-n-Pepa (the duo consisting of Cheryl James and Sandra Denton) for "Push It".

[22] Nominees for the 32nd Annual Grammy Awards included De La Soul for "Me Myself and I", DJ Jazzy Jeff & The Fresh Prince for "I Think I Can Beat Mike Tyson", Public Enemy for "Fight the Power", Tone Lōc for "Funky Cold Medina", and Young MC for "Bust a Move".

[23] "Me Myself and I" appears on De La Soul's studio album 3 Feet High and Rising and in 2008 was ranked number 46 on VH1's list of the 100 Greatest Hip Hop Songs Ever!!!

[30] "Funky Cold Medina", written by Young MC, Michael L. Ross and Matt Dike, first appeared on Tone Lōc's debut album Lōc-ed After Dark.

[32] Allmusic editor Stephen Thomas Erlewine described the song as "unabashed catchy" due to its "skittish, rhythmic guitar riff, looped beats", backing vocals, and "funny" rhymes.

[7] In 2010, Joshua Ostroff of Spinner included Young MC's win on his list of "The Grammy Awards' Biggest Mistakes", asserting that "Bust a Move" was merely a "fun little hip-pop song" while "Fight the Power" was a "revelatory single that still stands tall as one of music's greatest (and funkiest) political statements and perhaps hip-hop's finest moment".