The victim and a passenger were in his convertible around 10:45pm Saturday, headed north on Irvington near Yorkshire in north Houston. That's when police said another car drove up beside them.
Investigators said someone in the second car started shooting without warning. It is unknown how many shots were fired.
The driver of the convertible was shot in the head and crashed the car into a ditch on Yorkshire. He was rushed to Memorial Hermann Hospital in critical condition.
The passenger was not hurt.
Officials said the suspect vehicle fled the area.
It's not clear if the shooting was random or if the men were targeted.
Anyone with information can call police or Crime Stoppers.