As a choreographed stunt, it would be very difficult and dangerous, but might be possible. The drop plane would need to be in a nearly-vertical dive, since a skydiver in free fall is falling nearly vertically, at a rate of about 10000 feet per minute. Most planes can't dive like this- either they are moving too much horizontally (which will kill the skydivers) or they are essentially falling at their terminal velocity (which is, for most planes, much faster than the skydivers and also Vne).
As a practical matter, it's definitely impossible, and it would be incredibly reckless for a pilot to try. Skydivers don't usually pull their chutes immediately after exit and drop planes don't usually dive at Vne just in case one of the chutes fails. In other words, the skydiver is probably closer to the ground than to the plane by the time they discover their chute isn't working.
Even if the diver immediately radioed the plane and the plane immediately started a max-performance dive at Vne before deploying their magic dive brakes that let it match speed with a skydiver, there simply isn't time for the drop plane to intercept the diver and then recover while the altimeter is still reading a positive number.
To put some numbers on it, suppose a PC-6 drops a diver off at 10000 feet. Less than a minute later, the diver tries to pop their chute at 3000 feet, while the PC-6 is passing through 9000 feet. With around a 10000 fpm descent rate, the diver has a little under 20 seconds to be saved. The PC-6 would have to have an average descent rate of 30000 fpm just to hit the ground at the same time as the diver. As 30000 fpm is around twice Vne for a PC-6, that is unlikely to end well.