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"How did a Los Angeles helicopter traffic pilot (Billy Covington, Robert Downey Jr.'s character) suddenly get so quickly "qualified" to fly those single-engine planes, not to mention the bigger twin-engine piston-driven C-123's??"
You brought yourself the answer to your first question: "he'd been a bush flyer in Canada" and thus we may assert that he has all the required licenses to fly a dual-engine plane, not to mention single-engine ones (with a commercial pilot license, you learn to do that).
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I'd have to quibble a bit with your answer. I have an unlimited commercial pilot's license, but I am certified ONLY in SEL (Single Engine Land) aircraft. A pilot must receive specific and separate training for multi-engine, complex aircraft (constant-speed prop, retractable gear, etc.), rotorcraft, etc., and receive a check ride from an FAA examiner before being type-rated--meaning he is certified to be pilot-in-command of the particular aircraft. Further, to pilot certain types of aircraft, a pilot must also be instrument rated, requiring yet additional training and check rides.
Typically, a pilot also receives some small amount of dual-time in an aircraft he has never flown before, to become acquainted with all aspects of that aircraft's performance characteristics--that is, if a pilot is flying an aircraft that is NOT his own. Insurance regulations, you know.
On the other hand, in situations such as that depicted in "Air America", administrators might abandon formal rules, and simply be sure you are type-rated for the general type of aircraft--single-engine, multi-engine, rotorcraft, etc., then give you a quick run-down of the performance characteristics (speeds, RPM, manifold pressure, weights, etc.) of the aircraft you are about to command.
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