The stunt was a filmed from a Learjet with a periscope camera system, a B-25Mitchell bomber with 3 cameras, cameras in the Jet Star and DC-9 and a camera in a helicopter. The stunt was a year in planning, cost one million dollars to rehearse and shoot and was performed near Durango, Colorado in November 1992.
From Anecdotage.com:
Cliffhanger Stunt
During the production of Cliffhanger (1993), famed stunt coordinator Simon Crane was enlisted to perform the greatest one-man aerial stunt in cinema history. His assignment? To exit the tail of a DC-9 at 15,000 feet and slide down a wind-buffeted connecting rope to the open door of a smaller JetStar getaway plane.
"During one rehearsal, flying at 140 knots (any slower and the engines could have stalled), Crane was winched out from the tail of the DC-9, briefly hit a patch of dead air, and was twice slammed into the plane's tail, forcing him to release from the rope and deploy his parachute.
For the actual filming of the stunt high over the Rocky Mountains, that part went off as planned, but when he neared the JetStar, the weighted end of the rope looped around its wing, hindering Crane's ability to hook up with the rescue winch being manned by someone inside the smaller plane. Suspended midair for more than a minute, Crane was growing fatigued in the subzero wind when the pilot chose to steer the plane toward him.
Miraculously, Crane made it inside the hatch, getting the all-important shot, but was immediately yanked back outsilde. As the crew listened to him sliding along the top of the plane, he released, missed being sucked into the roaring engine by about six feet, and blew over the tail into the wild blue yonder. He parachuted down and was picked up by a helicopter — his balls approximately 84 percent bigger than before the stunt."
