Does the airplane ever actually pass through the hoop?
No, it's a slight of hand/sight gag. It's on a tether to the pylon like thing on his head. Probably something like 2 pound test fishing line or light black thread that you can't see. Notice his head never stops moving, but he disguises it pretty good with his body movements. Towards the end, he reaches up and locks something so the line winds up instead of rotating. It's a pretty entertaining little bit, I think.
Type at you later,
Dan McEntee