Ring Pops seems like a good idea. Who wants to hold a lollipop when they could free up their hand by making the lollipop into a ring? Here's the thing. Your hand freely dangles around, which makes your ring pop touch everything around you on accident. Soon you have hairs and dust all over it. Plus the saliva starts to drip and coat your hand, making it sticky. Who likes to be sticky? You don't see any of those problems with a regular lollipop. Don't broke what isn't fixed.
That being said, as a 90s kid, you still couldn't resist buying one. For all its problems, the Ring Pop is the most fun way to eat a sucker, if only for the brief moment when you first put it on and it looks like you have a huge, tacky diamond.