Loom may not exactly be obscure by any standard, but I don't see it being mentioned nearly as much as, say, Day of the Tentacle or Monkey Island. But it was a truly revolutionary way of reimagining the adventure game genre, and in a very early age of point-and-click. No inventory, single mouse click interaction, using spells to interact with the environment...
Of course, you'll want to play the original floppy version to get the full story; the CD-ROM version had its dialogue heavily truncated to fit onto the CD.
What's your pick?
Is Toonstruck well known? And should it be?
This isn't so much a recommendation as I've never got round to playing it, but it doesn't come up that often.
"Live Action" Christopher Lloyd (Back to the Future, Who Framed Roger Rabbit etc.), in a cartoon world point and click adventure sounds amazing. I sort of daren't play it in case it's a let down.
save