Albert "Gus" Wing III had already deployed his parachute Saturday when he struck the left wing of the DHC-6 Twin Otter propeller plane at about 600 feet, a witness on the ground told police.
Wing was wearing a helmet-mounted camera, and one of the jumpers told the South Florida Sun-Sentinal the camera was rolling on her boyfriend at the start of the jump.
Both of Wing's legs were severed at the knees, but he managed to maneuver his parachute and land near the DeLand Airport, about 40 miles north of Orlando, DeLand Police Cmdr. Randel Henderson said.
He was airlifted to a hospital, where he later died, Henderson said.
The wisecracking 50-year-old was a legendary aerial photographer who had been jumping from planes for 30 years, the Sun-Sentinal reports.
Fourteen other skydivers were in the air at the time of the accident, Federal Aviation Administration spokeswoman Holly Baker said. The plane landed safely.
The FAA and National Transportation Safety Board were investigating.
Wing owned a production company, Flying Wings Production, according to the Web site of the company that organized Saturday's jump, Skydive DeLand.