I am playing Gin and Juice right now, with the notorious Snoop covered by the bluegrass Gourds. I also know of the Dynamite Hack cover of NWA’s Boyz In Tha Hood. However, I haven’t found any more. I really like it, and I’d like more suggestions on more of these hilarious covers. Anyone know of others?
Phish covered “Gettin Jiggy with it” once during the Hampton run in 98. It’s on their CD “Hampton Comes Alive”
String Cheese Incident covered “Jungle Boogie” (not traditionally a rap song, but the vocalist made it one) with the guy from the Fugees on vocals, however on the recording I have his mic didnt work and you can just faintly hear him rapping.
Yeah, and I believe they also did the Beastie Boys’ Sabotage about the same time, but heck if I’m gonna dig through my old tapes to find it (unless you’re really really interested).
Yeah they played Sabotage on the same Hampton run.
Also, qwerty, you’re talking about 5-27-00 in Costa Rica, I think. I have that show. 
I was there the first time Phish did “Sabotage” (Lemonwheel at Limestone, ME, 1998). My brain nearly exploded.