Before the weights fall half the height of the ring, the ring lifts off the ground...
When the two weights are at the top of the ring gravity is pulling them down but the ring contrains them to move in a circular direction - one down each side of the ring. At the top, the ring is thus exerting forces on the initially stationary weights that are almost (but not quite) equal and opposite to gravity. By Newton's laws of motion, therefore, the weights are exerting a force equal and opposite force downwards upon the ring.
Now imagine that the weights have slid to the about "2 oclock" and "10 oclock" positions (i.e. 30 degrees). They will now have accelerated due to the influence of gravity.
(In fact we know that if they've dropped a distance of "h" then their energy is mgh which must also be the same as their kinetic energy, 1/2 mv^2. IE we have v^2 = 2gh and so v^2 is proportional to the height dropped.
The weights, however, aren't just falling, they are constrained to travel in a circle (i.e. orbit) and so a centripetal force, directed to toward the centre of the ring, must be acting upon them to keep them going in a circle.
Note that this force is proportional to the v^2 so as the weights fall further, the centripetal force gets stronger.
Now some component of this force can be provided by gravity but (a) that force is constant and (b) the angle changes so it soon has less and less effect (and reaches zero if we get to the half-way mark).
We thus get the situation (before the weights reach half-way) where the forces exerted by the ring are dominant - the left and right components cancel out and all you are left with is a overall downward force being applied to the weights by the ring . This means that the weights are applying an equal and opposite upward force to the much lighter ring and, therefore, it lifts off the ground.
Once the weights go past the halfway mark, though, the ring will be pulled down very hard!