Coincidental that you would choose this video. Rory now owns the Cessna 180 MIA that appears in the rapper's Instagram video. Don't know for sure if he was the pilot.
Interestingly, in September I met the deceased at the field and shot the shit for a bit after they got back from the night that video was shot. Nice guy, and I am sorry for the loss.
While I certainly can't fathom their risk tolerance and decision making or condone what they were doing, they are professional stunt and extreme sport guys as well (one prior to injury and becoming a rapper). There is some method to their madness when they do these things; stunts involving airplanes are not the only seemingly crazy risks things they tackle. While they seem pretty carefree, a random "hold my beer and watch this" approach to what happened is also not likely. But perhaps not as much experience with the risks of wing walking didn't make up for running out of luck that day.