It happened at the Belmont Plateau around 6 a.m. Sunday.
Police say two men were sitting in their car when someone opened fire on them.
The driver was shot in the head and lost control of the car, causing him to crash into a fence and then a tree.
He was rushed to Penn Presbyterian in critical condition.
The passenger was injured in the crash, but is expected to be okay.
No weapons have been recovered, and no arrest has been made.