Two women were also injured in the collision at the junction of Monmouth Drive and Darnick Road, in Sutton Coldfield, shortly before 8pm on Monday night.
West Midlands Ambulance service sent four ambulances, a paramedic officer, a MERIT trauma doctor and a critical care paramedic to the scene, where they joined off-duty medics who were already trying to save the male motorcyclist.
A spokeswoman said: “When ambulance crews arrived, they found several off-duty medics who had stopped to render aid and were administering CPR to the motorcyclist, a man, who was in cardiac arrest.
"Ambulance crews and MERIT quickly took over treatment to administer advanced life support but sadly, despite everyone’s best efforts, nothing could be done to save the man and he was confirmed dead on scene a short time later."
The two women were both driving the cars involved in the crash, and were assessed by ambulance staff at the scene.
Both had sustained minor injuries, with one being taken to Good Hope Hospital for further checks while the other was discharged at the scene.
West Midlands Police has been approached for comment.