The shooting and crash scene spans two blocks on Walnut Street from 53rd to 55th streets.
The gunfire erupted around 1 a.m.
Police said a black Cadillac and a burgundy Jeep were headed west on Walnut when someone in the Jeep fired into the Cadillac, shooting the driver in the head.
Both vehicles then crashed into several parked cars, investigators said.
Police found the victim dead behind the wheel of the Cadillac, and said they believe he was in his 20s or early 30s. His name has not been released.
Investigators said multiple people riding in the Jeep left the scene after it crashed.
Police found an AR-15 rifle in the Jeep as well as a 30-round extended magazine.
Homicide detectives and crash scene investigators are still sorting out how this all played out.
George Taylor, a resident who lives by the scene of the crash, says he came outside in the dark and saw the Jeep in his yard and his wife's SUV after it was pushed onto the sidewalk.
"Violence on the streets everywhere in Philadelphia. They need to do something about it," Taylor said.
He says this is the second time in recent years that one of his family's vehicles has been totaled while parked on this street.
But in the 17 years of living here, this is the first time he says he's dealt with a shooting on the block.
"I'm upset because the young man got killed. I don't know why but he's dead. That's another black man dead," Taylor said.
Anyone with information can call Philadelphia police at 215-686-TIPS (8477).
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