Sydney teen Josh Taylor held a loaded revolver to his head and pulled the trigger in a game of Russian roulette.
His friends were around him as the gun's single bullet was fired.
Now the 19-year-old is clinging to life in Westmead Hospital while his family hold bedside vigil.
Police have been told Mr Taylor was sitting in a car with his mates outside the IGA Supermarket in Pitt Town in Sydney's northwest on Friday night when he played the dangerous game.
"We are aware a 19-year-old male received a serious gunshot wound to the head after reports he was involved playing Russian roulette with a loaded revolver," Detective Inspector Garry Sims told AAP.