A fifth student and two adults sustained less serious injuries.
The crash happened about 9:15 p.m. when an eastbound 2007 Hyundai Elantra carrying the students attempted to pass a 1956 Chevrolet across a double yellow line, according to the Medina post of the Ohio Highway Patrol.
When the Hyundai reached a hill crest, just west of Marks Road, it struck a westbound 1986 Chevrolet pickup, according to the report.
The driver of the Hyundai, Alexander J. Stipek, 17, and three of his passengers, Chase Dupratt, 18, Danny A. Cuellar, 17, and Ryan Hoffer, 16, were transported to MetroHealth Medical Center in Cleveland, where they were listed in critical condition Tuesday.
A fifth student in the car, Spencer McCoy, 17, sustained minor injuries.
All the students are residents of Olmsted Falls, according to the report.
The patrol said the driver of the pickup, Richard A. Sasack, 23, of North Royalton, was taken to Southwest General Hospital with moderate injuries.
The driver of the ’56 Chevy, John A. Lopiccolo Sr., 66, of Brunswick, was treated for minor injuries at the crash scene.