When I was kid I thought "Muddy Waters" is band, but when I found out it was one dude I was like what? But anyhow I love Muddy and he was one of my fav bluesman. But however,that name would suit better to a band.
I'm big Deadhead, but when I heard of Grateful Dead for a first time, I thought it was some grindcore metal band. I would say it's not the best name for bunch of hippies - but it totally rocks.
For names that I found to be utterly retarded, here's a few : Neutral Milk Hotel, Somebody Still Loves You Boris Yeltsin - also uncreative names like Fire, Death, Music etc. are really stupid IMO.