Easily the hands down winner in the "so bad it's good" category is the above clip from the ultra cheesy late 80's "children's musical" film Creating Rem Lezar, in which Rem and friends (channeling Godspell?) sing, dance & prance their way through Central Park and other parts of New York City.
This clip and the others from Creating Rem Lezar, including the one in which a mannequin of Rem comes to life and then, donning a blue mullet, sings two kids to sleep, are so bad and so wrong on so many levels, and yet, for some strange reason, they are addictive viewing.
Written, directed, produced and choreographed by Scott Zakarin and made in 1989, Creating Rem Lezar went straight to video but never made it as far as DVD. Recently rediscovered thanks to YouTube, this hard to find VHS is much coveted and apparently fetches $50 or more online. Meantime you can view numerous clips from it on YouTube, found under titles like "bad 80's video" or "Worse 80's video."