North Yorkshire Police said a black Ford Focus, a black Vauxhall Corsa and a green Volkswagen Bora were involved in the collision near Thirsk on Wednesday at around 9.25pm.
The boys, believed to be 17, died at the scene and five adults and two children were taken to hospital.
Officers said they believed the vehicles were travelling from Thirsk to Busby Stoop - and are appealing for anyone with information or dash-cam footage to get in touch.
"Two boys, believed to be 17 years old, sadly died at the scene. A further five people and two children have been taken to hospital," the force said.
A stretch of the road between Busby Stoop and Carlton Minniott was closed while the scene was examined, but North Yorkshire Police said it reopened at 4.45am.
Anyone with information is asked to call police on 101 quoting incident 12180039673.