Police are appealing for witnesses to a serious collision on the A169 near Pickering on Friday.
The collision occurred on Friday at about 10pm on the A169 Pickering to Whitby road, just north of the junction to Lockton, just over a mile north of the Fox and Rabbit Inn.
It involved a black Peugeot 106 travelling south on the A169 towards Pickering, and a black Mercedes car and a black Honda Civic, both travelling in the opposite direction towards Whitby.
The 24-year-old male driver of the Peugeot was seriously injured and was taken to James Cook Hospital.
The 22-year-old male passenger in the Peugeot also sustained serious injuries, and had to be freed from the vehicle by North Yorkshire Fire and Rescue Service.
He was taken to Hull Royal Infirmary. Both men remain in hospital at this time.
Two female occupants of the Mercedes were assessed at the scene by paramedics but did not require hospital treatment. The male and female occupants of the Honda were uninjured.
The road remained closed for more than five hours while police collision investigators carried out a thorough examination of the vehicles and the scene.
Police are appealing for anyone who may have seen the collision, or any of the vehicles involved prior to it, to contact them. Please dial 101, select option 2 and ask for TC 1854 Zoe Billings or the Major Collision Investigation Team, or email email@example.com. Please quote reference number 12150071972.