Emergency crews were called to Hawksview Street in Merrylands just after 5pm on Saturday after a Hyundai i30 and a Holden ute collided.
As a result of the impact, the Holden rolled, flipped upside down and smashed into a third car – a parked ute.
A 35-year-old man, who was a passenger in the Holden, was pronounced dead at the scene despite the efforts of paramedics.
The driver, a 23-year-old man, was taken to hospital for minor injuries and mandatory testing.
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The 37-year-old driver of the Hyundai miraculously escaped unharmed and he was also tested at Westmead Hospital.
The parked car was unoccupied at the time.
A crime scene has been established while officers work to determine the cause of the crash.
Witnesses or anyone who may possess dashcam footage are urged to contact police immediately.