Firefighters used cutting equipment to free the pair following Sunday's late night accident on the A82 Great Western Road between Drumchapel and Clydebank.
One of the men was confirmed dead at the scene and the other is in a critical condition in the city's Western Infirmary. No other vehicles were involved.
Part of the road was closed in both directions for more than five hours as police launched an investigation into the crash near the Great Western Retail Park.
Police have appealed for anyone with information to contact them.
One local man said work had been carried out to try to make the road safer.
He said: "There have been a number of accidents on this road, but work has been carried out to widen it and there are speed restrictions. It seemed to be a lot safer."
A Police Scotland spokesman appealed for any witnesses to contact the force by calling 101.
It is the second road accident firefighters in the area have been called out to in recent days.
On Friday, three women were cut from a car after crashing on Duntocher Road.
One of them was taken to the Western Infirmary for treatment.
The station commander at Clydebank said:"It is vital that all motorists recognise the risks and take action to prevent further tragedy.
"Even the most experienced drivers can be caught out by variable conditions at this time of year, with low winter sun and unpredictable weather and [wet] surfaces."