The first Skymaster, model 336, had fixed landing gear and first flew on February 28, 1961.  It went into production in May 1963, and 195 were produced through mid 1964.

In February 1965 Cessna introduced the model 337 Super Skymaster. The model was larger, and had more powerful engines, retractable landing gear, and a dorsal air scoop for the rear engine ("Super" was subsequently dropped from the name).  In 1966 the turbocharged T337 was introduced, and in 1973 the pressurized P337G entered production.

Cessna built 2,993 Skymasters of all variants, including 513 military O-2 versions.  Production in America ended in 1982 but continued with Reims in France with the FTB337 STOL and the military FTMA Milirole. Production totalled 94 units.

The Skymaster handles differently from a conventional twin-engine aircraft, primarily in that it will not yaw into the dead engine if one engine fails. Without the issue of differential thrust inherent to conventional (engine-on-wing) twins, engine failure on takeoff will not produce yaw from the runway direction. With no one-engine-out minimum controllable speed(Vmc), in-flight control at any flying speed with an engine inoperative is not as critical as it is with engines on the wing with the associated leverage. Nevertheless, the Skymaster requires a multi-engine-rating, although many countries issue a special "centerline thrust rating" for Skymaster and other like-configurated aircraft.

The Skymaster produces a unique sound: a combination sound of its rear propeller slicing through turbulent air from the front prop and over the airframe, while its nose propeller addresses undisturbed air.