Here are some vidcaps from "It's a Mad, Mad, Mad Mad World", a 1963 movie about a wacky treasure hunt. Not sure who the stunt pilots were, but the legendary Paul Mantz and Frank Tallman are credited as the "aerial supervisors", so it may have been the masters themselves. Bear in mind that the exterior shots are not model shots ; these are real airplanes doing really crazy things.
Here are Mickey Rooney and Buddy Hackett trying to find a plane ride so they can beat the others to the treasure. There's a gorgeous Beech 18 there, but its owner, played by Jim Backus, is passed out on the pool table...

A cold shower and a Bloody Mary, and he's good to go...

Backus sends Mickey back to fix him a drink ("The only way to fly, you know"). This plane has a pop-up bar... nice.

Backus is not happy with his Old Fashioned, so he decides to go fix one for himself, leaving Buddy at the helm...

Of course, Buddy can't keep her level, and Backus is knocked unconscious during an upset.

Now the fun begins. Things are not too bad until an obstacle is spotted...

I love this shot. This is obviously a prop billboard, but that is a real Beech 18, and it's really flying right through it. Woopee!!

More to come...