It happened around 9pm Saturday on F.M. 1960 at Gilder.
The Corvette hit a Chevy Impala. Then a Ford Expedition hit the Impala and a Toyota Camry crashed into it, officials said.
Another car swerved into a pole to avoid the accident and another car was hit by flying debris.
The Corvette driver was ejected in the crash. He and two passengers from the Impala were taken to Ben Taub General Hospital in critical condition, officials said.
Two people in the SUV and the driver of the Impala went to the hospital with less severe injuries.
Deputies said there were no obvious signs of alcohol involved, but the crash remains under investigation.