From Homestar Runner Wiki
Coach Z is a rapper whose singles include "Rap Song" (accidentally featuring Peacey P), "These Peoples Try To Fade Me" and "Hip Hop Dance." He has dressed up as rappers Flavor Flav (Homestarloween Party), Humpty Hump (The House That Gave Sucky Treats), Kool Moe Dee (3 Times Halloween Funjob), 2Pac (Halloween Fairstival), Queen Latifah (Happy Hallow-day), and DJ Lance Rock (Most in the Graveyard) and is also a fan of Wu-Tang Clan. Other than his three singles, Coach Z's only known rap song is his musical rampage with Strong Bad in rampage. He also accidentally recorded a song over Strong Bad's speech in your funeral. According to the Yearbook Character Page, Coach Z claims to have been a chart-topping rapper in his home country. In the drama club performance in being mean, Coach Z performed "Being Mean Ain't the Greatest Choice." In Strong Badia the Free, when Homestar describes to Marzipan that Coach Z, joined the enemy, he calls him "the traitorous Coach Z" and claims that that is his "new rap name".
Strong Bad is a fan of the genre and the show Yo! MTV Raps (12:00), and has been shown to rap a few times, including in Everybody to the Limit. He has also created the Dog Food Gangstas. Also, many of his email intros feature a rap style.
The Cheat is a DJ who plays hip hop and other genres, such as indietronic (geddup noise). He assisted Strong Bad in making the video for his rap song Everybody to the Limit (earning a pizza) and remixed the King of Town's "Not Talkin' 'bout Butter" in hip hop form (Marzipan's Answering Machine Version 13.2).
- A DJ scratch is one of the available sounds in Audition with Marzipan.
- "Poot-Slap" by 3-Dee is a rap song of sorts.
- In New Boots, The Cheat dances a hip-hop dance on Homestar with his boots, after he pours hot soup on Homestar's eyes.
- In Halloween Potion-ma-jig, Homestar mentions "rap music" and asks Strong Sad what he would rap at a party.
- Crack Stuntman is seen rapping positive messages to kids and teens in An Important Rap Song.
- In Teen Girl Squad Issue 13, one minor character that appears is Peacey P, a rapper that The Ugly One seems to admire. His voice and singing style is very similar to that of Snoop Dogg.