The two car crash happened at around 9:30 p.m. Saturday in the 4500 block of D Street in Feltonville.
Officials say a classic 1950 Plymouth flipped several times after hitting a newer-model Mitsubishi that was trying to make a left turn.
The driver of the Plymouth, a 37-year-old man, is hospitalized in critical condition.
His passenger is in stable condition.
The driver of the Mitsubishi and his passenger are also hospitalized.
