His management team said he had been preparing for the stunt for months and had been training "intensively".
"His final act included performing an airplane stunt that included rapping while walking on the wing. He had trained intensely for this stunt; however, as Jon got further out onto the wing of the plane, it caused the small Cessna to go into a downward spiral that the pilot couldn't correct," a statement from his team said.
"Jon held onto the wing until it was too late, and by the time he let go, he didn't have time to pull his chute. He impacted and died instantly."
The pilot managed to regain control of the plane and land it safely just minutes later.
Jon's body was found in a hay field by farmer Sydney Fox. She told Global News that she heard the plane flying low over their house just moments before.
Jon, who was originally from Calgary, was married to 26-year-old Playboy model Kali James.
His childhood friend, professional skier Rory Wayne Bushfield, told The Canadian Press that he had an "unbelievable talent" for music.
"It was a tragedy when he broke his back... but he took that as a positive and it drove him to do some incredible things," he said.
Bushfield said his friend was determined to make the airplane stunt work and had been practicing for months.
"He planned for everything. It should have been straightforward. It's one of those things. We're not really sure what happened.
"Life is short, we all know that. He shone so bright. We know he knew the risks," he said. "He's inspired us so much and will forever."
Authorities said they are still investigating Jon's death.
They said Jon was part of a team filming plane and parachuting stunts and that no one else was injured.
He was initially a professional skier but turned his focus to music after suffering a broken back and shattered heel in a skiing accident several years ago.
