Air Racing has been around for nearly as long as there has been planes. Some of the first races were long distance events such as flying from England to Australia. Such events help develop long distance flying as a commercial and passenger enterprise.
Recently air races have become popular again, though in the current format small acrobatic planes fly close to the ground through a series of obstacles. As with the pilots in the very early flights on primitive planes, the current pilots would have to have no fear and lots of skill, and a bit of craziness.
The event to look out for is the Red Bull Air Race World Championship series of races, in which competitors fly one at a time through a series of pylons (air gates). Another air racing competition is the Aero GP which has been held each year since 2005. Aero GP air racing pits multiple planes racing against each other in a tight pylon circuit.
And soon to a sky near you - the Rocket Racing League where real-life pilots blast through real skies in real rockets, though on virtual tracks which they see using special helmets.