His black Mercedes saloon collided with the lorry on the A168 near Grafton at about 10.15am on Wednesday, June 26.
Ambulance crews attended but the man, believed to be in his 40s, was pronounced dead at the scene.
The lorry driver was not seriously hurt.
Police have closed the road to investigate the incident.
At 3.45pm officers have warned that it is likely to be shut for some time.
Motorists are advised to use alternative routes.
North Yorkshire Police are appealing for anyone who witnessed the crash, or saw either vehicle in the moments leading up to it, to contact them. They are also asking anyone with dashcam footage to get in touch.
To contact North Yorkshire Police, dial 101 and select option 1. Please quote reference NYP-26062019-0132.