Police are appealing for witnesses to come forward following the fatal collision shortly before 10am on the A64 East Bound at Grimston Bar.
It involved a Triumph Rocket Motorcycle and a black VW Passatt .
Officers investigating the incident are asking anyone with "dash cam" footage to send it to police.
The rider of the motorcycle, a man in his early fifties from the Nottingham area, died at the scene.
The pillion passenger, a woman in her early fifties, was taken to the Leeds General Infirmary by air ambulance with serious injuries.
The occupants of the VW Passatt, from the Durham area, were not injured but extremely shaken.
Anyone who witnessed the collision is asked to contact police. Dial 101, press two and ask to speak to TC Cobb in the Major Collision Investigation Team.
And anyone who has dash cam footage is asked to send it to [email protected]
Quote reference number NYP-06052018-0203 when passing on any information.